UNITED STATES
SECURITIES AND EXCHANGE COMMISSION
WASHINGTON, DC 20549
SCHEDULE 14A
Proxy Statement Pursuant to Section 14(a) of the Securities
Exchange Act of 1934 (Amendment No.    )
Filed by the Registrant  þ
Filed by a Party other than the Registrant  ¨
Check the appropriate box:
 
¨
Preliminary Proxy Statement
¨Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2))
þDefinitive Proxy Statement
¨Definitive Additional Materials
¨Soliciting Material Pursuant to § 240.14a-12
Tiptree Financial Inc.

(Name of Registrant as Specified in its Charter)
       
(Name of Person(s) Filing Proxy Statement, if Other Than the Registrant)
Payment of Filing Fee (Check the appropriate box):
þNo fee required.
¨Fee computed on table below per Exchange Act Rules 14a-6(i)(1) and 0-11.
(1)Title of each class of securities to which transaction applies:
(2)Aggregate number of securities to which transaction applies:
(3)Per unit price or other underlying value of transaction computed pursuant to Exchange Act Rule 0-11 (set forth the amount on which the filing fee is calculated and state how it was determined):
(4)Proposed maximum aggregate value of transaction:
(5)Total fee paid:
(1)Title of each class of securities to which transaction applies:
(2)Aggregate number of securities to which transaction applies:
(3)Per unit price or other underlying value of transaction computed pursuant to Exchange Act Rule 0-11 (set forth the amount on which the filing fee is calculated and state how it was determined):
(4)Proposed maximum aggregate value of transaction:
(5)Total fee paid:
¨Fee paid previously with preliminary materials.
¨Check box if any part of the fee is offset as provided by Exchange Act Rule 0-11(a)(2) and identify the filing for which the offsetting fee was paid previously. Identify the previous filing by registration statement number, or the Form or Schedule and the date of its filing.
 
(1)Amount Previously Paid:
(2)Form, Schedule or Registration Statement No.:
(3)Filing Party:
(4)Date Filed:








tiptree_logoxupdateda.jpg









2022
(1)Amount Previously Paid:
ANNUAL MEETING OF SHAREHOLDERS
PROXY STATEMENT

TIPTREE INC.


(2)Form, Schedule or Registration Statement No.:
(3)Filing Party:
(4)Date Filed:






tiptree_logoxupdateda.jpg
Tiptree Financial Inc.
780 Third299 Park Avenue, 21st13th Floor
New York, New York 1001710171
April 27, 201622, 2022
Dear Stockholder:
You are invited to attend the
The Annual Meeting of Stockholders (the “Annual Meeting”) of Tiptree Financial Inc. This year’s meeting(the “Company” or “Tiptree”) will be held virtually only via live audio webcast at www.virtualshareholdermeeting.com/TIPT2022, on Monday,Tuesday, June 6, 2016,7, 2022, at 9:30 a.m., local4:00 p.m. Eastern time (EST). You will be able to attend the meeting online and submit questions during the meeting by visiting the website listed above. You will also be able to vote your shares electronically at 780 Third Avenue, 21st Floor, New York, NY 10017.the Annual Meeting. As always, we encourage you to authorize a proxy to vote your shares prior to the annual meeting.
On or about April 27, 2016, we
We are delivering the attached proxy statement, with the accompanying formal notice of the meeting, which describes the matters expected to be acted upon at the meeting. We urge you to review these materials carefully and to vote on the matters described in the accompanying proxy statement. If you wish

Virtual Meeting Admission. Stockholders of record as of April 14, 2022 will be able to attendparticipate in the Annual Meeting by visiting our Annual Meeting website at www.virtualshareholdermeeting.com/TIPT2022. To participate in person, we askthe Annual Meeting, you will need the 16-digit control number included on your proxy card or on the instructions that accompanied your proxy materials. The Annual Meeting will begin promptly at 4:00 p.m. EST on Tuesday, June 7, 2022. Online check-in will begin at 3:45 p.m. EST, and you reserve your seat by May 31, 2016 by contacting us at (212) 446-1400 or IR@tiptreefinancial.com.should allow approximately 15 minutes for the online check-in procedures. Additional details regarding requirements for admission to the Annual Meeting are described in the attached proxy statement under the heading “How docan I obtain admission toattend the virtual Annual Meeting?”
Your vote is important. Whether you plan to virtually attend the meeting or not, please authorize a proxy to vote your shares either over the Internet, by toll-free telephone or by completing the enclosed proxy card and returning it as promptly as possible. You may continue to have your shares of common stock voted as instructed over the Internet, by toll-free telephone or in the proxy card, or you may change your vote either by votingauthorizing a proxy to vote your shares again before 11:59 p.m., Eastern Time, on June 5, 2016,6, 2022, the time at which the Internet and telephone votingproxy authorization facilities close, or, if you attend the meeting,Annual Meeting virtually, by submitting a proxy card prior to orvoting at the virtual meeting.
 
Sincerely,
Sincerely,
/s/ Jonathan Ilany
Jonathan Ilany
Chief Executive Officer





TIPTREE FINANCIAL INC.
780 Third299 Park Avenue,
21st 13th Floor
New York, NY 1001710171
NOTICE OF ANNUAL MEETING OF STOCKHOLDERS
You are hereby invited to attend the 20162022 Annual Meeting of Stockholders of Tiptree Financial Inc.
WHENMonday,Tuesday, June 6, 2016,7, 2022, at 9:30 a.m.4:00 p.m., local time.
EST.
WHERE
780 Third Avenue, 21st Floor, New York, NY 10017. If you wish to attendVirtually via audio webcast
Participate in the Annual Meeting by visiting our Annual Meeting website at www.virtualshareholdermeeting.com/TIPT2022.
There will not be a physical meeting in person, we ask that you reserve your seat by May 31, 2016 by contacting us at (212) 446-1400New York or anywhere else
IR@tiptreefinancial.com
. Additional details regarding requirements for admission to the Annual Meeting are described in the attached proxy statement under the heading “How docan I obtain admission toattend the virtual Annual Meeting?”
ITEMS OF BUSINESS•To elect two (2) Class III directors to serve for a term expiring at the 2019 Annual Meeting (Proposal 1);
•To ratify the selection of KPMG LLP (“KPMG”) as our independent registered public accounting firm for the fiscal year ending December 31, 2016 (Proposal 2); and
•To conduct such other business as may properly come before the meeting or any adjournment or postponement thereof.
RECORD DATEStockholders of record as of the close of business on April 18, 201614, 2022 will be entitled to notice of and to vote at the 20162022 Annual Meeting of Stockholders.
ITEMS OF BUSINESS(1) To elect two (2) Class III directors to serve for a term expiring at the 2025 Annual Meeting (“Proposal 1”);(2) To approve an amendment to the Tiptree Inc. 2017 Omnibus Incentive Plan to increase the number of shares of the Company’s common stock available for awards thereunder by an additional 4,000,000 shares (“Proposal 2”);(3) To ratify the selection of Deloitte & Touche LLP (“Deloitte”) as our independent registered public accounting firm for the fiscal year ending December 31, 2022 (“Proposal 3”); and
(4) To conduct such other business as may properly come before the meeting or any
adjournment or postponement thereof.
VOTING BY PROXY OR PROXY AUTHORIZATIONTiptree Financial Inc., on behalf of the Board of Directors, is soliciting your proxy to ensure that a quorum is present and that your shares are represented and voted at the 20162022 Annual Meeting of Stockholders. Whether or not you plan to virtually attend the Annual Meeting, please authorize a proxy to vote either over the Internet, by toll-free telephone or by completing, signing, dating and promptly returning the enclosed proxy card in the postage-prepaid envelope provided. For specific instructions on voting, please refer to the instructions on the proxy card or the information forwarded by your broker, bank or other holder of record. If you attend the Annual Meeting virtually, you may vote in person (virtually) if you wish, even if you have previously voted.given your proxy. Please note, however, that if your shares are held of record by a broker, bank or other nominee and you wish to vote in person (virtually) at the virtual meeting, you must obtain a proxy issued in your name from such broker, bank or other nominee.

RECOMMENDATIONS
The Board of Directors recommends that you voteImportant Notice Regarding the Availability of Proxy Materials for our Annual Meeting to be held on June 7, 2022: “FOR” each nominee for director (Proposal 1) and “FOR” the ratification of KPMG as our independent registered public accounting firm for 2016 (Proposal 2).

We encourage you to receive all proxy materials in the future electronically to help us save printing costs and postage fees, as well as natural resources in producing and distributing these materials. If you wish to receive these materials electronically next year, please follow the instructions on the proxy card.
By Order of our Board of Directors,
/s/ Neil C. Rifkind
Neil C. Rifkind
Secretary
New York, New York
April 27, 2016




IMPORTANT NOTICE REGARDING THE AVAILABILITY OF PROXY MATERIALS FOR
THE ANNUAL MEETING TO BE HELD ON June 6, 2016:
Financial and other information concerning Tiptree Financial Inc. (“Tiptree”) is contained in our Annual Report on Form 10-K for the fiscal year ended December 31, 2015,2021, including financial statements, filed with the Securities and Exchange Commission (“SEC”)SEC on March 15, 201614, 2022 (the “2015“2021 10-K”). Under rules issued by the SEC, we are providing access to our proxy materials both by sending you this full set of proxy materials, including a proxy card, and by notifying you of the availability of our proxy materials on the Internet. The proxy materials and our Annual Report are available at http://www.proxyvote.com.
By Order of our Board of Directors,
/s/ Neil C. Rifkind
Neil C. Rifkind
Secretary
New York, New York
April 22, 2022



Table of Contents
 Page
1
1
2
4
5
17
17
1
Who is entitled to vote at the meeting?
17
17
17
8
28
28
29
39
310
310
310
410
411
4
Who should I contact if I have any questions?
411
12
12
14
15
15
15
16
16
16
17
17
17
18
18
18
18
20
20
i

422
522
523
24
624
EXECUTIVE OFFICERS
7
CORPORATE GOVERNANCE MATTERS
8
926
1026
1130
1131
1231
Director Attendance at Annual Meetings
12
12
Executive Sessions of Independent Directors
13
Current Board Leadership Structure
13
Board’s Role in Risk Oversight
13
CNG Committee Interlocks and Insider Participation
14
AUDIT COMMITTEE REPORT
14
PROPOSAL 2:3: RATIFICATION OF APPOINTMENT OF THE INDEPENDENT REGISTERED PUBLIC ACCOUNTING FIRM
1532
1532
1532

i


Ratification
15
32
1532
16
COMPENSATION DISCUSSION AND ANALYSIS
1634
1734
1836
1938
1938
2040
20
20152021 Executive Compensation Program and Decisions
2141
24
Separation Payments to Mr. Kauffman
25
Tax Deductibility of NEO Compensation
2642
2643
2643
2643
2743
28
Grants of Plan-Based Awards
3145
31
Option Exercises and Stock Vested
3246
3347
33
Potential Payments to Named Executive Officers Upon Termination or Change in Control
3348
3351
3452
3452
Section 16(a) Beneficial Ownership Reporting Compliance
36
3754
3754
3755
56
ii

3856
3957
3957
3957
4058
59
60

iii
ii



TIPTREE FINANCIAL INC.
780 Third Avenue
21st Floor
New York, NY 10017tiptree_logoxupdateda.jpg
PROXY STATEMENT
FOR THE 2016 ANNUAL MEETING OF STOCKHOLDERSSUMMARY
To be held2022 Annual Meeting Information
Date and Time:Tuesday, June 7, 2022, at 4:00 p.m., EST.
Location:Virtually via audio webcast
Participate in the Annual Meeting by visiting our Annual Meeting website at www.virtualshareholdermeeting.com/TIPT2022.
There will not be a physical meeting in New York or anywhere else
Record Date:April 14, 2022
Mailing Date:On or about April 22, 2022

Meeting Agenda and Board Recommendations
PROPOSALSTHE BOARD’S VOTING RECOMMENDATIONS:Page
1.To elect two (2) Class III directors to serve for a term expiring at the 2025 Annual Meeting (Proposal 1); and
“FOR” each nominee for director (Proposal 1)
22
2.To approve an Amendment to the Tiptree Inc. 2017 Omnibus Incentive Plan to increase the number of shares of the Company’s common stock available for awards thereunder by an additional 4,000,000 shares (Proposal 2);
“FOR” (Proposal 2)
24
3.To ratify the selection of Deloitte & Touche LLP (“Deloitte”) as our independent registered public accounting firm for the fiscal year ending December 31, 2022 (Proposal 3).
“FOR” (Proposal 3)
32

How to Vote

You can vote by any of the following methods:
By Internet:Go to www.proxyvote.com
By Phone:Call 1-800-690-6903
By Mail:Complete, sign, date and mail the proxy card in the postage paid envelope provided.
In Person:Attend the Annual Meeting virtually and vote in person (virtually)

If you authorize a proxy to vote your shares by Internet or phone, you must do so no later than 11:59 p.m. Eastern Time on June 6, 20162022.

1

Tiptree Performance in 2021
2021 was one of Tiptree’s best years since its founding in June 2007 and we made meaningful progress on our long-term strategic initiatives while delivering a strong increase in shareholder value. Tiptree’s revenues, earnings and total return to shareholders all set records. Our specialty insurer, Fortegra also produced record results, with adjusted return on equity of 22% while growing premiums and equivalents at 32%. In addition, our mortgage and shipping businesses also reported excellent results for the year, benefiting from favorable market conditions. Below is a summary of our 2021 results. Additional information on our 2021 results is contained in our Annual Report on Form 10-K for the year ended December 31, 2021 filed with the SEC.

Full-Year 2021 Summary

($ in thousands, except per share information)FY’21FY’20
Total revenues$1,200,514 $810,301 
Net income (loss) attributable to common stockholders$38,132 $(29,158)
Diluted earnings per share$1.09 $(0.86)
Cash dividends paid per common share$0.16 $0.16 
Return on average equity11.4 %(6.4)%
Non-GAAP: (1)
Adjusted net income$63,869 $51,431 
Adjusted return on average equity16.5 %13.1 %
Adjusted EBITDA$100,776 $4,541 
Book value per share$11.22 $10.90 

•Revenues of $1.2 billion, increased 48.2%, driven by growth in insurance and shipping operations and investment gains in 2021 compared to losses in 2020. Excluding the impact from investment gains and losses, revenues increased 32.9% versus prior year.
•Net income attributable to common stockholders of $38.1 million, increased significantly from a net loss in 2020, represented an annualized return on average equity of 11.4%.

•Adjusted net income(1) of $63.9 million, increased 24.2%, reflecting higher earnings in insurance and shipping operations. Adjusted return on average equity(1) of 16.5%, compared to 13.1% in 2020.

•Adjusted EBITDA(1) was $100.8 million, an increase of $96.2 million from 2020, driven by realized and unrealized gains in 2021 compared to losses in 2020 (primarily Invesque), in addition to the improved operating performance noted above.

•On October 12, 2021, Tiptree announced a $200 million investment in Fortegra from Warburg Pincus, which is expected to close in the second quarter of 2022 and is expected to result in an approximate 24% ownership of the business on an as converted basis.

Insurance (The Fortegra Group)

2

($ in thousands)FY’21FY’20
Gross written premiums and premium equivalents$2,194,024 $1,666,942 
Revenues$984,130 $691,061 
Income before taxes$69,857 $26,948 
Return on average equity17.1 %8.1 %
Combined ratio90.6 %91.5 %
Non-GAAP: (1)
Adjusted net income$66,782 $43,423 
Adjusted return on average equity22.2 %15.2 %

•Fortegra’s gross written premiums and premium equivalents increased 31.6% for the year driven by growth in its U.S. specialty insurance lines and service contract businesses in the U.S. and Europe. As a function of Fortegra’s premium growth, the combination of unearned premiums and deferred revenues on the balance sheet grew to $1,658.8 million, up $399.1 million, or 31.7%, from 2020.

•Revenues increased 42.4% for the year driven by premium growth and investment gains in 2021 compared to losses in 2020. Excluding the impact of investment gains and losses, revenues increased by 39.5% over 2020.

•For total year 2021, the combined ratio was 90.6%, compared to 91.5% in 2020. Operating and technology efficiencies contributed to an improved expense ratio, while the underwriting ratio remained stable.

•Total year 2021 income before taxes was $69.9 million compared to $26.9 million in the prior year. Return on equity was 17.1% for 2021, as compared to 8.1% in 2020.

•Adjusted net income(1) for 2021 was $66.8 million, up 53.8% from 2020, driven by revenue growth and an improved combined ratio. The adjusted return on average equity(1) was 22.2% for 2021, as compared to 15.2% in 2020.

Tiptree Capital

($ in thousands)FY’21FY’20
Revenues$216,384 $119,240 
Income before taxes$45,617 $(30,140)
Return on average equity22.2 %(12.7)%
Non-GAAP: (1)
Adjusted net income$28,197 $33,075 
Adjusted return on average equity16.2 %17.8 %

•Mortgage income before taxes was $28.4 million in 2021, as compared to $31.1 million in 2020, with the decrease driven by a decline in gain on sale margins, partially offset by higher servicing fees and positive fair value adjustments on the mortgage servicing portfolio. Return on average equity was 22.2% and Adjusted return on average equity was 28.8% in 2021.

•Maritime transportation income before taxes was $11.6 million in 2021, as compared to $1.5 million in 2020, with the increase driven by cyclically high dry-bulk charter rates.

3

•Within Tiptree Capital, our investment in Invesque contributed unrealized gains of $3.1 million in 2021 compared to a loss of $67.7 million in 2020.

(1)For a reconciliation to GAAP financials, see “Annex B: Non-GAAP Measures”

Tiptree Long Term Performance
We believe that our performance is best measured over the long term and that long term growth in our stock price plus dividends paid is the best metric for evaluating our performance. The table below shows growth in our stock price plus dividends paid annually and since inception(1) (June 2007) during the one, three and five year period from December 31, 2021, compared with the S&P 500, Russell 2000 and S&P Select Sector Financial Services Index, with all values calculated with dividends reinvested.
TiptreeS&P 500S&P Financial Select SectorRussell 2000
1 Year178.7%28.7%35.0%14.8%
3 Year37.7%26.0%20.6%20.0%
5 Year19.4%18.5%13.2%12.0%
From Jun’079.7%10.5%4.0%8.6%

(1)    At inception in 2007, book value per share was $5.36.

Stock Performance Graph
Set forth below is a line-graph presentation comparing the cumulative total return on our common stock against cumulative total returns of the Russell 2000 and the S&P Select Sector Financial Services Index(1). The performance graph shows the total return on an investment of $100 for the period beginning December 31, 2016 and ending December 31, 2021 assuming reinvestment of dividends. The stockholder return shown on the graph below is not necessarily indicative of future performance, and we will not make or endorse any predictions as to future stockholder returns. The graph and related data were furnished by ICR, LLC.
4

performancestockcharta.jpg

(1) We believe it is difficult to develop a peer group of companies similar to Tiptree as Tiptree owns subsidiaries engaged in a number of diverse business activities. However, management views Tiptree and its subsidiaries as primarily engaged in financial services as of December 31, 2021 and accordingly, management has used the Standard and Poor’s Select Sector Financial Services Index for comparative purposes.

Compensation Highlights

2021 was a milestone year for the Company as we achieved record levels of financial and stock price performance. A key performance objective for our performance-based stock options granted in past years was to achieve a 20-day volume weighted average stock price greater than the book value per share on the date of grant. This hurdle was achieved in 2021 for all stock options granted to our Executive Committee (collectively, the Executive Chairman and Chief Executive Officer) from 2017-2020.

In order to continue to focus, motivate and reward our Executive Committee, in August 2021, the Compensation, Nominating and Governance Committee (the “CNG”) decided to change its incentive pay program to focus on achievement of stock price rather than book value.Prior to 2021, the incentive pay program for our Executive Committee (with the exception of 2020) was based on annual payments of 3.0% of Adjusted EBITDA for the Executive Chairman and 4.5% of Adjusted EBITDA for the Chief Executive Officer, allocated 55% in the form of cash, 30% in the form of restricted stock units (“RSUs”) with three-year cliff vesting and 15% in the form of stock options tied to performance and time vesting criteria. The new incentive pay program provides for an annual bonus in the form of a cash payment equal to 3.5% of Adjusted EBITDA to each of the Executive Chairman and the Chief Executive Officer and a one-time award of performance restricted stock units (the “PRSUs”) for each of the Executive Chairman, the Chief Executive Officer and Tiptree’s President, intended to cover three-years of long-term incentive opportunity (i.e., the Executive Chairman, the Chief Executive Officer and Tiptree’s President will not receive another long-term incentive award under the program until 2024). Tiptree’s President was included in the PRSU program to recognize his ability to impact shareholder value and to align his reward structure with that of the Executive Committee.
5


The PRSUs were established with the following objectives for our Executive Committee and President:
•Focus management on near-term and long-term opportunities to create shareholder value and deliver robust total shareholder returns over the next ten years

•Deliver extraordinary compensation value through the PRSUs only for extraordinary total shareholder returns (i.e., ~ 20% annualized total shareholder return over the performance period)

With these objectives in mind, the CNG Committee developed a PRSU design structure based on a goal of achieving stock price hurdles.Under the terms of the PRSUs, the maximum number of shares can only be earned by delivering an annualized total shareholder return of approximately 20%, which is equivalent to growing the stock price to more than six times the base value of $9.70 (Tiptree’s closing stock price on August 4, 2021, the date the PRSUs were granted). While there are opportunities to receive shares earlier by achieving lower share price targets, the PRSU design back-loads the number of shares eligible to be earned toward the higher share price targets (for example, 60% of the PRSUs vest upon the final two stock price targets of $45 and $60).

The table below summarizes the PRSU awards to the Executive Committee and the President and includes the number of shares eligible to vest upon achievement of each stock price hurdle (adjusted for dividends paid), the determination period when such price targets must be met, the minimum annualized total shareholder return required to be achieved prior to the end of such determination period in order to earn the shares and the increase in Tiptree’s market value at achievement of each price target.
Price TargetShares EarnedDetermination Period
Minimum Annualized Return through End of Determination Period(1)
Incremental Increase of Tiptree’s Market Value at Price Target(2)
Shares Earned as Percentage of Shares Outstanding(3)
$15233,333Before August 4, 202324.35%$182,243,6910.67%
$20466,667Before August 4, 202519.83%$183,722,8251.34%
$30700,000Before August 4, 202720.70%$374,445,6401.98%
$45933,333Before August 4, 202921.14%$582,668,4452.59%
$601,166,667Before August 4, 203119.99%$624,668,4753.16%

(1) Based on grant date closing stock price of $9.70.
(2) Based on 34,877,897 shares outstanding as of March 31, 2022, the increase in Tiptree’s market value at achieving each price target as compared to a share price of $9.70 at grant of the PRSUs, assuming Tiptree’s shares outstanding increases solely to include the incremental common stock issued for vested PRSUs at achievement of each price target.
(3) At the $15 price target, this is based on 34,877,897 shares outstanding as of March 31, 2022. At each subsequent price target, the shares outstanding is increased solely to include the incremental common stock issued for vested PRSUs at achievement of each price target.

The PRSU grants amount to 3,500,000 maximum shares in the aggregate; however, none of these shares will be earned unless management delivered the minimum annualized returns required within the determination periods outlined above. To date, the first stock price hurdle of $15 has been met.

6

tiptree_logoxupdateda.jpg
QUESTIONS AND ANSWERS ABOUT THE ANNUAL MEETING
What is the purpose of the meeting?
At the Annual Meeting, stockholders will be asked to vote on:
the election of two (2) Class III directors to serve for a term expiring at the 2019 annual meeting of stockholders (Proposal 1);
the ratification of KPMG LLP (“KPMG”) as our independent registered public accounting firm for the fiscal year ending December 31, 2016 (Proposal 2); and
any other matters that may properly be brought before the Annual Meeting or at any adjournments or postponements thereof.
How how does the Board of Directors recommend I vote on these proposals?
The Board of Directors recommends a vote:
“FOR” the electionpurpose of the Annual Meeting is for stockholders to vote on the following two (2) nomineesproposals, which are included in this Proxy Statement. Tiptree’s Board recommends that you vote your shares as indicated below.
PROPOSALSTHE BOARD’S VOTING RECOMMENDATIONS:Page
1.To elect two (2) Class III directors to serve for a term expiring at the 2025 Annual Meeting (Proposal 1);
“FOR” each nominee for director (Proposal 1)
22
2.To approve an amendment to the Company’s 2017 Omnibus Incentive Plan to increase the number of shares of the Company’s common stock available for awards thereunder by an additional 4,000,000 shares (Proposal 2); and
“FOR” (Proposal 2)
24
3.To ratify the selection of Deloitte & Touche LLP (“Deloitte”) as our independent registered public accounting firm for the fiscal year ending December 31, 2022 (Proposal 3).
“FOR” (Proposal 3)
32

Other than the proposals described in this Proxy Statement, the Board is not aware of any other matters to be presented for a vote at the Annual Meeting. If you grant a proxy by telephone, Internet or by signing and returning your proxy card, any of the persons appointed by the Board of Directors as Class III directors: Jonathan Ilanyproxy holders — Sandra Bell and Lesley Goldwasser (Proposal 1); andNeil C. Rifkind — will have the discretion to vote your shares on any additional matters properly presented for a vote at the Annual Meeting. If any of our nominees is unavailable as a candidate for director, the above-named proxy holders will vote your proxy for another candidate or candidates as may be nominated by the Board of Directors.
“FOR” the ratification of the selection of KPMG as our independent registered public accounting firm for the fiscal year ending December 31, 2016 (Proposal 2).
Who is entitled to vote at the meeting?meeting?
If our records show that you were a holder of our common stock at the close of business on April 18, 2016,14, 2022, which is referred to in this proxy statement as the “record date,” you are entitled to receive notice of the meetingAnnual Meeting and to vote the shares of common stock that you held as of the close of business on the record date.
How many shares can vote?
As of the close of business on the record date of April 18, 2016, 34,928,26414, 2022, there were 34,886,865 shares of Class A common stock and 8,049,029 shares of Class B common stock of Tiptree Inc. (“Tiptree” or the Company were“Company”) issued and outstanding and entitled to vote.outstanding. There are no other classes of voting securities outstanding. You are entitled to one (1) vote for each share of Class A or Class B common stock you held as of the close of business on the record date.
What constitutes a quorum?
A quorum of stockholders is necessary to hold a valid meeting. A quorum will be present if at least a majority of the outstanding shares entitled to vote are represented at the Annual Meeting. As of the close of business on April 18, 2016, the record date of April 14, 2022, there were 42,977,29334,886,865 shares outstanding and entitled to vote. Thus, 21,488,64717,443,433 shares must be represented at the Annual Meeting to have a quorum.
Your shares will be counted towards the quorum if you vote in person (virtually) at the Annual Meeting or if you submit a valid proxy (or one is submitted on your behalf by your broker, bank or other nominee). Additionally, abstentions and broker non-votes will also be counted towards the quorum requirement. If there is no quorum, the Chairman of the Annual Meeting may adjourn the meeting until a later date.

7

How docan I obtain admission toattend the virtual Annual Meeting?
All stockholders at the close of business on the Record Date are invited to attend the Annual Meeting. All stockholders planning to attend theThe Annual Meeting in person must reservewill be a seatcompletely virtual meeting of stockholders conducted exclusively by May 31, 2016 by contacting us at (212) 446-1400 or IR@tiptreefinancial.com. For admission, stockholders should come to the Annual Meeting check-in area no less than 15 minutes before the Annual Meeting is scheduled to begin. Stockholdersa live audio webcast.

If you are a stockholder of record should bring a form of photo identification so their share ownership can be verified. A beneficial owner holding shares in “street name” must also bring an account statement or letter from his or her bank or brokerage firm showing that he or she beneficially owns shares as of the close of business on April 14, 2022, the record date along withfor the Annual Meeting, you will be able to virtually attend the Annual Meeting, vote your shares and submit your questions online during the meeting by visiting www.virtualshareholdermeeting.com/TIPT2022. You will need to enter the 16-digit control number included on your notice, on your proxy card or on the instructions that accompanied your proxy materials.

If your shares of common stock are held by a formbroker, bank or other nominee (i.e., in “street name”) as of photo identification. Thethe close of business on April 14, 2022, you may gain access to the meeting by following the instructions in the voting instruction card provided by your broker, bank or other nominee. You may not vote your shares electronically at the Annual Meeting unless you receive a valid proxy from your brokerage firm, bank, broker dealer or other nominee holder.

The online meeting will begin promptly at 4:00 p.m., EST on June 7, 2022. We encourage you to access the meeting prior to the start time. Online check-in will begin at 9:30 a.m.3:45 p.m., local time.EST, and you should allow approximately 15 minutes for the online check-in procedures.

If you wish to submit a question for the Annual Meeting, you may do so in advance at www.virtualshareholdermeeting.com/TIPT2022, or you may type it into the dialog box provided at any point during the virtual meeting (until the floor is closed to questions).

What can I do if I need technical assistance during the Annual Meeting?
If you encounter any difficulties accessing the virtual Annual Meeting webcast, please call the technical support number that will be posted on the Annual Meeting website log-in page.
How do I vote?
•For Proposal 1 (election of directors), you may either vote “FOR” all of the nominees to the Board of Directors or you may “WITHHOLD” your vote for all of the nominees or for any nominee that you specify.

•For Proposal 2 (ratification(approval of the appointment of KPMG)amendment to the Tiptree Inc. 2017 Omnibus Incentive Plan), you may vote “FOR” or “AGAINST” such proposal or “ABSTAIN” from voting.

•For Proposal 3 (ratification of the appointment of Deloitte), you may vote “FOR” or “AGAINST” such proposal or “ABSTAIN” from voting.
The procedures for voting are set forth below:below:
Stockholder of Record: Shares Registered in Your Name.  If you are a stockholder of record, you may vote in person (virtually) at the Annual Meeting or vote by giving your proxy authorization over the Internet, by telephone or by properly completing, signing and dating the accompanying proxy card where indicated and mailing the card in the postage paid envelope provided. Whether or not you plan to virtually attend the Annual Meeting, we encourage you to vote by proxy or to give your proxy authorization to ensure that your votes are counted. You may still virtually attend the Annual Meeting and vote in person (virtually) if you have already voted by proxy or given your proxy authorization.

•VOTE BY INTERNET — You may authorize a proxy to vote your shares by internetInternet at www.proxyvote.com. Use the Internet to transmit your voting instructions and for electronic delivery of
8

information up until 11:59 PM Eastern TimeEST on June 5, 2016.6, 2022. Have your proxy card in hand when you access the web sitewebsite and follow the instructions to obtain your records and to create an electronic voting instruction form.


•VOTE BY PHONE — You may authorize a proxy to vote your shares by calling 1-800-690-6903. Use any touch-tone telephone to transmit your voting instructions up until 11:59 PM Eastern TimeEST on June 5, 2016.6, 2022. Have your proxy card in hand when you call and then follow the instructions.


•VOTE BY MAIL — Mark, sign and date your proxy card and return it in the postage-paid envelope we have provided or return it to Tiptree Financial Inc., Vote Processing, c/o Broadridge, 51 Mercedes Way, Edgewood, NY 11717.11717 so that it is received by June 6, 2022.


•VOTE IN PERSON (VIRTUALLY) — You may vote in person by attending(virtually) during the Annual Meeting. AtMeeting at www.virtualshareholdermeeting.com/TIPT2022 by using the meeting, you will need to request a ballot to vote. See “How do I obtain admission at the Annual Meeting” for additional information.16-digit control number included with these proxy materials.
Beneficial Owner: Shares Registered in the Name of Broker, Bank or Other Nominee.    If your shares of common stock are held by a broker, bank or other nominee (i.e., in “street name”), you will receive instructions from your nominee, which you must follow in order to have your shares of common stock voted. Such stockholders who

We encourage you to receive all future proxy materials electronically to help us save printing costs and postage fees, as well as natural resources in producing and distributing these materials. If you wish to vote in person atreceive these materials electronically next year, please follow the Annual Meeting will need to obtain ainstructions on the proxy form from the broker, bank or other nominee that holds their shares of common stock of record.card.
How is my vote counted?
If you authorize a proxy to vote your shares through the Internet, by phone or properly execute the accompanying proxy card, and if we receive it by 11:59 p.m., Eastern Time, on June 5, 2016,6, 2022, the shares of common stock that the proxy represents will be voted in the manner specified on the proxy. If no specification is made in the proxy, your shares of common stock that the proxy represents will be voted in accordance with the recommendations of our Board of Directors set forth in this proxy statement. It is not anticipated that any matters other than those set forth in the proxy statement will be presented at the Annual Meeting. If other matters are presented, proxies will be voted in accordance with the d


iscretiondiscretion of the proxy holders. In addition, no stockholder proposals or nominations were received on a timely basis, so no such matters may be brought to a vote at the Annual Meeting.
What vote is needed to approve each proposal?

•For Proposal 1 (election of directors), the vote of a plurality of all of the votes cast at the Annual Meeting, assuming a quorum is present, is required for the election of a director. Therefore, the two nominees for director receiving the most “FOR” votes will be elected. For purposes of the election of directors, abstentionsvote on Proposal 1, withheld votes and broker non-votes, if any, will not be counted as votes cast and will have no effect on the result of the vote, although they will be considered present for the purpose of determining the presence of a quorum.

•For Proposal 2 (ratification(approval of an amendment to the appointment of KPMG)Company’s 2017 Omnibus Incentive Plan), the affirmative vote of a majority of all of the votes cast at the Annual Meeting, assuming a quorum is present, is required for approval of Proposal 2. For purposes of the vote on Proposal 2, abstentions and broker non-votes, if any, will not be counted as votes cast and will have no effect on the result of the vote, although they will be considered present for the purpose of determining the presence of a quorum.

•For Proposal 3 (ratification of the appointment of Deloitte), the affirmative vote of a majority of all of the votes cast at the Annual Meeting, assuming a quorum is present, is required for approval of Proposal 3. For purposes of the vote on Proposal 3, abstentions will not be counted as votes cast and will have no effect on the result of the vote, although they will be considered present for the purpose of determining the presence of a quorum. We do not expect any broker non-votes for this proposal.
9


How are abstentions and “broker non-votes” and abstentions treated for purposes of the proposals?
Under the laws of Maryland, the state of Tiptree’s incorporation, abstentions generally do not constitute a vote “for” or “against” any matter being voted on at the Annual Meeting and generally will not be counted as “votes cast.” Therefore, abstentions and “broker non-votes” will have no effect on any of the proposals. “Broker non-votes” will be treated in the same manner as abstentions for purposes of the Annual Meeting.
Brokers, banks, or other nominees that have not received voting instructions from their clients cannot vote on their clients’ behalf with respect to “non-routine” proposals, but may vote their clients’ shares on “routine” proposals. Although the determination of whether a nominee will have discretionary voting power for a particular item is typically determined only after proxy material are filed with the SEC, we expect both Proposal 1 (election of directors) is aand Proposal 2 (approval of an amendment to the Company’s 2017 Omnibus Incentive Plan) to be considered non-routine proposal. Conversely,proposals. We expect that Proposal 23 (ratification of appointment of KPMG) isDeloitte) will be considered a routine proposal. In the event that a broker, bank, or other nominee indicates on a proxy that it does not have discretionary authority to vote certain shares on a non-routine proposal, then those shares will be treated as broker non-votes. Abstentions and broker non-votes will be treated as present for the purpose of determining the presence of a quorum.
What other information is part of thisthe proxy statement?materials?
The proxy materials include a letter to stockholders and our 20152021 Annual Report which is comprised of the 20152021 10-K. The 20152021 10-K and this Notice and Proxy Statement and Form of Proxy are available, free of charge, on our website at http://www.tiptreefinancial.com.www.tiptreeinc.com. The information found on, or accessible through, our website is not incorporated into, and does not form a part of, this proxy statement. You may also obtain a copy of our 20152021 Annual Report or the 20152021 10-K, free of charge, by directing your request in writing to Tiptree Financial Inc., 780 Third299 Park Avenue, 21st13th Floor, New York, NY,10017,New York 10171, Attn: Secretary, or by calling our corporate number at (212) 446-1400. Our other filings made with the SEC are also accessible on our website and available at no charge on the SEC’s website at http://www.sec.gov.
Can I change my vote after I submit my proxy card or give instructions over the Internet or telephone?
Yes. If you are the record holder of your shares, you may revoke your proxy in one of three ways:
•filing a written notice (via e-mail) revoking the proxy with our Secretary at our address;legal@tiptreeinc.com;
•signing and forwarding to us a properly executed proxy with a later date;date or authorizing another proxy over the Internet or telephone; or
•appearing in person (virtually) and voting by ballot at the Annual Meeting.Meeting at
www.virtualshareholdermeeting.com/TIPT2022 by using the 16-digit control number included with these proxy materials.
Whether or not you vote using a traditional proxy card, through the Internet or by telephone, you may use any of those three methods to change your vote. Accordingly, you may change your vote either by submitting a proxy card prior to or at the Annual Meeting or by votingauthorizing a proxy again before 11:59 p.m., Eastern Time, on June 5, 2016,6, 2022, the time at which the Internet and telephone votingproxy authorization facilities close. The later submitted vote will be recorded and the earlier vote revoked. If you virtually attend the Annual Meeting, you may vote in person (virtually) whether or not you have previously given a p


roxy,proxy, but your presence, (withoutvirtually or otherwise, without further action)action at the meetingAnnual Meeting will not constitute revocation of a previously given proxy.
If your shares are held by your broker, bank or other nominee, you should follow the instructions provided by your broker, bank or nominee.
How can I determine the results of the voting at the Annual Meeting?
Preliminary voting results will be announced at the Annual Meeting. Final results will be announced in a Current Report on Form 8-K, which will be filed with the SEC within four business days after the conclusion of the Annual Meeting. If final results are unavailable at the time we file the Form 8-K, then we will file an amended
10


report on Form 8-K to disclose the final voting results within four business days after the final voting results are known.
Who is soliciting my proxy?
This solicitation of proxies is made by and on behalf of our Board of Directors. We will pay the cost of the solicitation of proxies. In addition to the solicitation of proxies by mail, our directors, officers and employees may solicit proxies personally or by telephone.
We have hired Morrow & Co.,Sodali LLC, 470 West Ave., Stamford, CT 06902 (“Morrow”), to help us distribute and solicit proxies. We will pay approximately $5,000$2,500 in fees, plus expenses and disbursements, to Morrow for its proxy solicitation services.
No person is authorized on our behalf to give any information or to make any representations with respect to the proposals other than the information and representations contained in this proxy statement, and, if given or made, such information and/or representations must not be relied upon as having been authorized and the delivery of this proxy statement shall, under no circumstances, create any implication that there has been no change in our affairs since the date hereof.
Can I obtain a list of stockholders entitled to vote at the Annual Meeting?
At the Annual Meeting, and at least ten days prior to the Annual Meeting, a complete list of stockholders entitled to vote at the meeting will be available at our principal office, 780 Third Avenue, 21st Floor, New York, NY, 10017, during regular business hours. Stockholders of record may inspect the list for proper purposes during normal business hours.
Who should I contact if I have any questions?
If you have any questions about the Annual Meeting, this proxy statement, our proxy materials or your ownership of the Company’s common stock, please direct your request in writing to Tiptree Financial Inc., 780 Third299 Park Avenue, 21st13th Floor, New York, NY, 10017,10171, Attn: Secretary, or call our corporate number at (212) 446-1400.
11
PROPOSAL 1: ELECTION OF DIRECTORS

Our board
CORPORATE GOVERNANCE MATTERS
This section of directors is classified into three classes: Class I, consistingour proxy statement contains information about our corporate governance policies and practices. You can visit the governance documents section of Bradley E. Smith and Richard A. Priceour corporate website at http://www.tiptreeinc.com to hold office for a term expiring at the 2017 annual meeting of stockholders; Class II, consisting of Michael G. Barnes and Mr. John E. Mackview or to hold office for a term expiring at the 2018 annual meeting of stockholders and Class III, consisting of Jonathan Ilany and Lesley Goldwasser to hold office for a term expiring at the 2016 annual meeting of stockholders.
Our Third Amended and Restated Bylaws (“Bylaws”) provide that a majorityobtain copies of the entireCompany’s Bylaws, Charter, CNG Committee Charter, Audit Committee Charter, Code of Business Conduct and Ethics and Corporate Governance Guidelines. The information found on, or accessible through, our website is not incorporated into, and does not form a part of, this proxy statement or any other report or document we file with or furnish to the SEC. You may also obtain, free of charge, a copy of our Bylaws, Charter, CNG Committee Charter, Audit Committee Charter and Code of Business Conduct and Ethics Corporate Governance Guidelines by directing your request in writing to Tiptree Inc., 299 Park Avenue, 13th Floor, New York, NY, 10171, Attn: Secretary or by calling our corporate number at (212) 446-1400.
The Board of Directors may establish, increase or decrease the numberand its Committees
Our business and affairs are overseen by our Board of directors, provided that the number of directors shall never be less than one (1), which is the minimum number required byDirectors pursuant to the Maryland General Corporation Law nor more than fifteen (15).

(the “MGCL”) and our Charter and Bylaws. Members of the Board of Directors are kept informed of the Company’s business by participating in Board and committee meetings, by reviewing materials provided to them and through discussions with the Chairman and CEO and with key members of management.

Information Regarding the Nominees for Election
The following tableCompany has elected to be subject to Section 3-804(c) of the MGCL (the “Opt-In”), which is a common practice among Maryland corporations with classified boards. As a result of the Opt-In, the Board has the exclusive power to fill vacancies on the Board, and biographical descriptionsany director elected by the Board to fill a vacancy will hold office for the remainder of the full term of the class of directors in which the vacancy occurred and until his or her successor is elected and qualified.

The average age of our directors, including our director nominees, is 59 years. The average tenure of our directors, including our director nominees as of the 2022 Annual Meeting, is expected to be approximately six years.

Our Board of Directors presently consists of seven members: Michael G. Barnes, Paul M. Friedman, Lesley Goldwasser, Jonathan Ilany, Randy Maultsby, Dominique Mielle and Bradley E. Smith. The Board of Directors has affirmatively determined that Messrs. Friedman and Smith and Mses. Goldwasser and Mielle are independent as that term is defined in Nasdaq Stock Market Rules and SEC regulations.

The Board of Directors currently has two standing committees: an Audit Committee and a CNG Committee.

During fiscal 2021, our Board of Directors held nine meetings, the Audit Committee held eight meetings and the CNG Committee held eight formal meetings and several informal discussions among the members of the CNG Committee and its independent compensation consultant. All of our directors during fiscal 2021 attended at least 75% of the aggregate number of meetings of our Board of Directors and each committee of the Board of Directors on which they served during fiscal 2021.
Audit Committee
Our Board of Directors has established an audit committee that meets the definition provided by Section 3(a)(58)(A) of the Securities Exchange Act of 1934, as amended (the “Exchange Act”). Currently the Audit Committee is comprised of our four independent directors: Messrs. Friedman and Smith and Mses. Goldwasser and Mielle. The current Audit Committee members satisfy the definition of independence set forth certain information,in the Nasdaq Stock Market Rules and Rule 10A-3 under the Exchange Act. Mr. Friedman was appointed as the Chairman of April 27, 2016, with respectthe Audit Committee on August 24, 2020. He was determined by our Board of Directors to each nominee for electionbe an “audit committee financial expert” as director atthat term is defined in the Annual Meeting. Mr. Ilany and Ms. Goldwasser each currently serve as a director.Exchange Act.
12

NomineesThe Audit Committee is responsible for Election as directorsAgeDirector Sinceoverseeing:
Class III• our accounting and financial reporting processes;
Jonathan Ilany63August 2010• the quality and integrity and audits of our consolidated financial statements, and accounting and reporting processes;
Lesley Goldwasser• our compliance with legal and regulatory requirements;
• the qualifications and independence of our independent registered public accounting firm; and
54January 2015• the performance of our independent registered public accounting firm and any internal auditors.
The Audit Committee is also responsible for engaging the independent registered public accounting firm, reviewing with the independent registered public accounting firm the plans and results of the audit engagement, approving professional services provided by the independent registered public accounting firm and considering the range of audit and non-audit fees.
Compensation, Nominating and Governance Committee
The CNG Committee is comprised of our four independent directors: Messrs. Friedman and Smith and Mses. Goldwasser and Mielle. Ms. Mielle was appointed as the Chair of the CNG Committee on August 24, 2020.
The CNG Committee is responsible for:
• establishing our corporate goals and objectives relevant to the Executive Committee’s compensation, reviewing the Executive Committee’s performance in light of such goals and objectives and evaluating and approving the performance of, and the compensation paid by the Company to, the Executive Committee in light of such goals and objectives;
• reviewing and evaluating the performance of, and recommending to the Board of Directors the compensation of, our executive officers other than the Executive Committee, considering our corporate goals and objectives and evaluating the performance of such executive officers in light of such goals and objectives;
• overseeing the compensation policies and programs of our non-executive officer employees to determine whether such compensation policies and programs are functioning effectively or create any unreasonable risk to the Company, as well as reviewing the appropriateness of the compensation practices to determine if they are reasonably likely to have a material adverse effect on the Company;
• reviewing, evaluating and recommending to the Board of Directors any incentive plan or material revision thereto, and administering the same;
• reviewing and approving the disclosure regarding our compensation and benefit matters in our proxy statement and Annual Report;
• identifying, recruiting and recommending to the full Board of Directors qualified candidates for election as directors and recommending a slate of nominees for election as directors at the annual meeting of stockholders;
• developing and recommending to the Board of Directors corporate governance guidelines and policies;
• recommending to the Board of Directors compensation for service as directors in accordance with our corporate governance guidelines;
• overseeing the evaluation of the structure, duties, size, membership and functions of the Board of Directors and its committees and recommending appropriate changes to the Board of Directors; and
• establishing procedures to exercise oversight of the evaluation of the Board of Directors and its committees and members (including a self-evaluation).
13

The CNG Committee has the authority to retain, at the Company’s expense, independent legal, accounting and other consultants, advisors and experts that it reasonably determines to be necessary or appropriate to assist the committee in the performance of its responsibilities. For 2021, the CNG Committee engaged Compensation Advisory Partners LLC (“CAP”) as its independent compensation consultant to help advise it on the design of our executive compensation program and the compensation opportunities thereunder. See “Use of Independent Compensation Consultant” below for further details on the services provided by our independent compensation consultant in 2021.
Jonathan
Director Compensation
The following table sets forth information regarding the compensation paid to, or earned by our directors, during fiscal 2021:
Director Compensation Fiscal 2021
NameFees Earned or Paid in Cash
($)
Stock
Awards
($)(1)(2)
Total
($)
Michael G. Barnes(3)
———
Paul M. Friedman$115,008$103,848$218,856
Lesley Goldwasser$95,025$129,796$224,821
Jonathan Ilany(3)
———
Randy Maultsby(3)
———
Dominique Mielle$110,008$103,848$213,856
Bradley E. Smith$75,025$129,796$204,821
(1)The number of shares granted is based on the volume weighted average price for the ten trading days prior to the end of the quarter. The grant date closing market price of our common stock for each quarterly payment on each of April 7, 2021, July 6, 2021, October 6, 2021 and January 7, 2022 was $9.93, $8.88, $10.45, and $13.39, respectively.
(2)Represents the grant date fair value of shares granted, as recognized by the Company for financial statement reporting purposes in the fiscal year ended December 31, 2021 in accordance with Accounting Standards Codification 718 — Compensation — Stock Compensation. See Note 19, Stock Based Compensation, to our consolidated financial statements in 2021 Annual Report on Form 10-K.
(3)Messrs. Barnes, Ilany is and Maultsby receive no compensation in connection with their service on our Board. The compensation that they receive in their capacity as Executive Chairman, Chief Executive Officer and a memberPresident, respectively, is included in the Summary Compensation Table below.
Non-Employee Director Compensation Program
In fiscal 2021, each non-employee director was eligible to receive an annual cash retainer of $100,000 plus $100,000 in immediately vested shares of our Executive Committee. He is also a membercommon stock, both of which are paid quarterly in arrears. Such non-employee directors may elect to receive up to $125,000 of total compensation in the form of immediately vested common stock and the cash compensation payable to such director would be reduced proportionately. The Lead Director received an additional $20,000 annual retainer, the Chair of the Audit Committee receives an additional annual retainer of $15,000 and the Chair of the CNG Committee received an additional annual retainer of $10,000. In addition, we reimburse all directors for reasonable out-of-pocket expenses incurred in connection with their services on our Board of Directors. From February 2015
14

Principal Executive Officer Pay Ratio
Set forth below is a reasonable estimate of the ratio of annual total compensation of the Company’s principal executive officer (“PEO”) to November 2015,the median of the annual total compensation of all employees, other than the PEO. The Company views the Executive Committee, consisting of Mr. Barnes, its Executive Chairman, and Mr. Ilany, its Chief Executive Officer, collectively as the Company’s PEO.  
In 2021, we identified the median employee (such person, the “Median Employee”) by using as our consistently applied compensation measure, 2021 gross earnings, as reported on Form W-2 (“W-2 gross earnings”), for all individuals who were employed by the Company and its subsidiaries on December 31, 2021, other than our principal executive officers. We included all employees, whether employed on a full-time, part-time or seasonal basis, and we did not annualize the compensation of any full-time employee who was employed for less than the full 2021 calendar year. We believe that the use of W-2 gross earnings is an appropriate measure by which to determine the Median Employee because it accurately represents annual compensation earned by our Co-Chief Executive Officer. From October 2014 until February 2015, heemployees.

Messrs. Barnes and Ilany had 2021 annual total compensation of $8,877,686 and $9,168,916, respectively, as reflected in the Summary Compensation Table included in this Proxy Statement under “Executive Compensation—Summary Compensation”. Using the same methodology used to calculate Messrs. Barnes and Ilany’s 2021 total compensation in the Summary Compensation Table, our Median Employee’s total compensation for 2021 was $84,137. As a result, we estimate that Messrs. Barnes’s and Ilany’s 2021 annual total compensation was approximately 106 times and 109 times, respectively, that of our Executive Vice President, HeadMedian Employee.
Because the SEC rules for identifying the median of Mortgage Financethe annual total compensation of our employees and Asset Management. Mr. Ilany servedcalculating the pay ratio based on the employee’s annual total compensation allow companies to adopt a variety of methodologies, to apply certain exclusions, and to make reasonable estimates and assumptions that reflect their employee populations and compensation practices, the pay ratio reported by other companies may not be comparable to the pay ratio for the Company.
Corporate Governance Guidelines
Our Board of Directors has adopted Corporate Governance Guidelines that address significant issues of corporate governance and set forth procedures by which our Board of Directors carries out its responsibilities. Among the areas addressed by the Corporate Governance Guidelines are director qualification standards, director responsibilities, director relationships and access to management and independent advisors, director compensation, director orientation and continuing education, management succession, annual performance evaluation of the Board of Directors and management responsibilities. Our CNG Committee is responsible for assessing and periodically reviewing the adequacy of the Corporate Governance Guidelines and will recommend, as appropriate, proposed changes to the Board of Directors.
Code of Business Conduct and Ethics
Our Board of Directors has adopted a Code of Business Conduct and Ethics that applies to our directors, executive officers (including our principal executive officer and principal financial and accounting officer) and employees, as well as employees of any person or its affiliates that provide services to us. The Code of Business Conduct and Ethics was designed to assist our directors, executive officers and employees, as well as employees of any person or its affiliates that provide services to us, in complying with the law, resolving moral and ethical issues that may arise and in complying with our policies and procedures. Among the areas addressed by the Code of Business Conduct and Ethics are compliance with applicable laws, conflicts of interest, use and protection of our Company’s assets, confidentiality, communications with the public, accounting matters, record keeping and discrimination and harassment.
We intend to satisfy our disclosure obligations under Item 5.05 of Form 8-K related to amendments or waivers of the Code of Business Conduct and Ethics by posting such information on our corporate website.
15


Stockholder Engagement and Communications with our Board of Directors
We have discussions with a variety of our stockholders throughout the year including one-on-one meetings and participation at investor conferences. In addition, we have a process by which stockholders and other parties may communicate with our Board of Directors, our independent directors as a directorgroup or our individual directors. Any such communications may be sent to our Board of Rescap,Directors in writing and should be directed to the Board of Directors, a subsidiary of Ally Bank from November 2011 until December 2013. Since 2005, Mr. Ilany has been a private investor and passive partner at Mariner Investment Group (“Mariner”). Mr. Ilany was a partner at Mariner from 2000 until 2005, responsible for hiring and setting up new trading groups, overseeing risk management, and servingcommittee, the independent directors as a senior membergroup, or an individual director at Tiptree Inc., 299 Park Avenue, 13th Floor, New York, NY, 10171, Attn: Secretary, who will forward all such appropriate communications on to the intended recipient. In addition, stockholder communications can be directed to our Board of Directors, a committee, the Investment Committee and Management Committee of the firm. From 1996-2000, Mr. Ilany wasindependent directors as a private investor. From 1982 until 1995, Mr. Ilany wasgroup or an employee of Bear Stearns & Co. (“Bear Stearns”) From 1980 until 1982, Mr. Ilany workedindividual director by calling our Corporate Governance Hotline at Merrill Lynch. From 1971 until 1975, Mr. Ilany served in the armored corps of the Israeli Defense Forces, and he was honorably discharged holding the rank of First Lieutenant. Mr. Ilany received his B.A. and M.B.A. from the University of San Francisco.(844) 877-5474. Any such communications may be made anonymously.

Mr. Ilany was selected and qualified
Director Attendance at Annual Meetings
Pursuant to serve as aour Corporate Governance Guidelines, we expect each member of our Board of Directors becauseto attend each annual meeting of his extensive riskstockholders. Last year, all of the directors attended the annual meeting of stockholders.
Identification of Director Candidates
As stated in the CNG Committee Charter, the CNG Committee assists our Board of Directors in identifying and reviewing director candidates to determine whether they qualify for membership on the Board and for recommending to the Board nominees to be considered for election at our annual meeting of stockholders.
In making recommendations to our Board of Directors, the CNG Committee considers such factors as it deems appropriate. Though the Company does not have a formal policy addressing diversity, the Board of Directors and the CNG Committee believe that diversity is an important attribute of the members who comprise our Board of Directors and that members should represent an array of backgrounds and experiences and should be capable of articulating a variety of viewpoints. As such, directors should have diversity with respect to background, skills and expertise, industry knowledge and experience. The CNG Committee uses the following general criteria for identifying director candidates:
•Directors should possess senior level management and senior managerialdecision-making experience;
•Directors should have a reputation for integrity and abiding by exemplary standards of business and professional conduct;
•Directors should have the commitment and ability to devote the time and attention necessary to fulfill their duties and responsibilities to the Company and its stockholders;
•Directors should be highly accomplished in their respective fields, with leadership experience in corporations or other complex organizations, including government, educational and military institutions;
•In addition to satisfying the independence criteria described in the Corporate Governance Guidelines, independent directors should be able to represent all stockholders of the Company;
•Directors who are expected to serve on a committee of the Board of Directors shall satisfy applicable legal requirements and other criteria established by any securities exchange on which our common stock is listed; and
•Directors should have the ability to exercise sound business judgment to provide advice and guidance to the Chief Executive Officer and Executive Chairman with candor.
The foregoing general criteria apply equally to the evaluation of all potential independent and management director nominees, including those individuals recommended by stockholders.
The Board of Directors’ assessment of an individual’s candidacy for director also includes consideration of diversity, age, skills and experience in the financial services industry, his board experiencecontext of the needs of the Board of Directors.
Our CNG Committee may solicit and his experience with investing in real estate and real estate-related assets and extensive knowledgeconsider suggestions of our business and industries.directors or our management regarding possible nominees. Our CNG Committee may also procure the services of outside sources or third parties to assist in the identification of director candidates.
16

Lesley Goldwasser has been a memberOur CNG Committee may consider director candidates recommended by our stockholders. Our CNG Committee will apply the same standards in considering candidates submitted by stockholders as it does in evaluating candidates submitted by members of our Board of Directors since January 5, 2015.or our management. Any recommendations by stockholders should follow the procedures outlined under “Additional Information — Stockholder Proposals” in this proxy statement and in our Bylaws.
Executive Sessions of Independent Directors
In accordance with our Corporate Governance Guidelines, the independent directors serving on our Board of Directors are given an opportunity at each meeting to meet in executive session without the presence of any directors or other persons who are part of our management. Our executive sessions were chaired by our Lead Director, Ms. Goldwasser has been a Managing Partner of GreensLedge Capital Markets LLC (“GreensLedge”) since September 2013. Prior to joining GreensLedge, Ms. Goldwasser was associatedGoldwasser. Interested parties may communicate directly with Credit Suisse Group AG (“Credit Suisse”)our Lead Director or our independent directors as a Managing Director from September 2010 to November 2013, where she had global responsibility forgroup through the Hedge Fund Strategic Services unit. Before Credit Suisse, Ms. Goldwasser spent 12 years at Bear Stearns. where she was co-headprocess set forth above under “Communications with our Board of Global Debt and Equity Capital Markets units and had global responsibility for structured products. Prior to her tenure at Bear Stearns, Ms. Goldwasser spent 12 years at Credit Suisse in a varietyDirectors.”
Current Board Leadership Structure
Our Board of management positions, including responsibility for bothDirectors is led by Michael G. Barnes, the Asset Backed and Non-Agency Mortgage Trading Desks. Ms. Goldwasser is a graduate of the University of Cape Town, South Africa.

Ms. Goldwasser was selected and qualified to serve as a memberChairman of our Board of Directors, becauseand our Executive Chairman.
Because the Chairman of her diversethe Board of Directors is not independent, the Board of Directors appointed Ms. Goldwasser to serve as the Company’s Lead Director and extensivepreside at executive sessions of the independent directors and at meetings of the Board of Directors when the Chairman is not present.
To help ensure that the Board of Directors carries out its oversight responsibilities, our Corporate Governance Guidelines require the Board of Directors as a whole to maintain independence from management. Pursuant to the Corporate Governance Guidelines, a majority of the Board of Directors must be independent. As of the date hereof, four of our current seven directors have been determined to be independent.
Board’s Role in Risk Oversight
Our Board of Directors oversees our business in general, including risk management and performance of the Executive Chairman, Chief Executive Officer and other members of senior management, to assure that the long-term interests of the stockholders are being served. Each committee of our Board of Directors is also responsible for reviewing the risk exposure related to such committee’s areas of responsibility and providing input to senior management on such risks.
Management and our Board of Directors have a process to identify, analyze, manage and report all significant risks facing us. Our Executive Chairman and Chief Executive Officers will regularly report to the Board of Directors on significant risks facing us, including legal, financial, operational and strategic risks. The Audit Committee reviews with senior management significant risks related to the Company and periodically reports to the Board of Directors on such risks.
In addition, pursuant to its charter, the Audit Committee is responsible for reviewing and discussing the Company’s business risk management process, including the quality and integrity of the Company’s financial statements, and accounting and reporting processes, the Company’s compliance with legal and regulatory requirements, the independent registered public accounting firm’s qualifications and independence, and the performance of the Company’s internal audit function. Furthermore, the Audit Committee evaluates key financial statement issues and risks, their impact or potential effect on reported financial information and the process used by management to address such matters. At each Audit Committee meeting, management briefs the committee on the current business and financial experience across a variety of investment banking disciplines.
All nominees for director have consented to be named and have agreed to serve as directors if elected. We have no reason to believe that anyposition of the nominees will be unableCompany, as well as such items as internal audits and independent audits.
17


Compensation Risk Assessment
The CNG Committee assessed our compensation policies and practices to accept election asevaluate whether they create risks that are reasonably likely to have a director. However,material adverse effect on the Company. Based on its assessment, the CNG Committee concluded that the Company’s compensation policies and practices, in conjunction with the eventCompany’s existing processes and controls, do not create incentives to take risks that one or more nominees are unable or unwillingreasonably likely to accept election orhave a material adverse effect on the Company.
CNG Committee Interlocks and Insider Participation
The following non-employee directors are unable to serve for any reason, the persons named as proxies or their substitutes will have authority, according to their judgment, to vote or refrain from voting for such substitute as may be designated bycurrent members of the CNG Committee of the Board of Directors.

Vote RequiredDirectors: Messrs. Friedman and the RecommendationSmith and Mses. Goldwasser and Mielle. During 2021, none of the Board
The vote ofCompany’s executive officers served as a plurality of alldirector or member of the votes cast at the Annual Meeting, assuming a quorum is present, is necessary for the electioncorporate governance committee of each Class III director. Therefore, the two nominees for director receiving the most “FOR” votes will be elected. For purposes of the election of directors, abstentions and broker non-votes, if any will not be counted as votes cast and will have no effectother entity whose executive officers served on the resultCompany’s Board of Directors or CNG Committee.

Prohibition of Hedging and Pledging Transactions
Our Tiptree Inc. Securities Trading Policy (“Insider Trading Policy”) prohibits short sales of and option trading on Tiptree stock and prohibits our directors and officers, other employees of Tiptree subject to the vote, although they will be considered presentInsider Trading Policy and their respective designees from engaging in hedging transactions, such as (but not limited to) zero-cost collars, equity swaps, exchange funds and forward sale contracts, that may allow such individual to continue to own Tiptree securities without the full risks and rewards of ownership.  Our Insider Trading Policy also prohibits holding Tiptree securities in a margin account or otherwise pledging Tiptree securities as collateral for the purpose of determining the presence of a quorum.loan.
THE BOARD OF DIRECTORS UNANIMOUSLY RECOMMENDS A VOTE “FOR”
EACH NOMINEE.



CONTINUING DIRECTORSThe Board of Directors and its Committees
Our business and affairs are overseen by our Board of Directors pursuant to the Maryland General Corporation Law (the “MGCL”) and our Charter and Bylaws. Members of the Board of Directors are kept informed of the Company’s business by participating in Board and committee meetings, by reviewing materials provided to them and through discussions with the Chairman and CEO and with key members of management.

The followingCompany has elected to be subject to Section 3-804(c) of the MGCL (the “Opt-In”), which is a common practice among Maryland corporations with classified boards. As a result of the Opt-In, the Board has the exclusive power to fill vacancies on the Board, and any director elected by the Board to fill a vacancy will hold office for the remainder of the full term of the class of directors will continuein which the vacancy occurred and until his or her successor is elected and qualified.

The average age of our directors, including our director nominees, is 59 years. The average tenure of our directors, including our director nominees as of the 2022 Annual Meeting, is expected to servebe approximately six years.

Our Board of Directors presently consists of seven members: Michael G. Barnes, Paul M. Friedman, Lesley Goldwasser, Jonathan Ilany, Randy Maultsby, Dominique Mielle and Bradley E. Smith. The Board of Directors has affirmatively determined that Messrs. Friedman and Smith and Mses. Goldwasser and Mielle are independent as directors.that term is defined in Nasdaq Stock Market Rules and SEC regulations.

The Board of Directors currently has two standing committees: an Audit Committee and a CNG Committee.

During fiscal 2021, our Board of Directors held nine meetings, the Audit Committee held eight meetings and the CNG Committee held eight formal meetings and several informal discussions among the members of the CNG Committee and its independent compensation consultant. All of our directors during fiscal 2021 attended at least 75% of the aggregate number of meetings of our Board of Directors and each committee of the Board of Directors on which they served during fiscal 2021.
Audit Committee
Our Board of Directors has established an audit committee that meets the definition provided by Section 3(a)(58)(A) of the Securities Exchange Act of 1934, as amended (the “Exchange Act”). Currently the Audit Committee is comprised of our four independent directors: Messrs. Friedman and Smith and Mses. Goldwasser and Mielle. The current Audit Committee members satisfy the definition of independence set forth in the Nasdaq Stock Market Rules and Rule 10A-3 under the Exchange Act. Mr. Friedman was appointed as the Chairman of the Audit Committee on August 24, 2020. He was determined by our Board of Directors to be an “audit committee financial expert” as that term is defined in the Exchange Act.
12

NameAgeDirector SinceThe Audit Committee is responsible for overseeing:
Class I• our accounting and financial reporting processes;
Richard A. Price (Chairman• the quality and integrity and audits of our consolidated financial statements, and accounting and reporting processes;
• our compliance with legal and regulatory requirements;
• the qualifications and independence of our independent registered public accounting firm; and
• the performance of our independent registered public accounting firm and any internal auditors.
The Audit Committee is also responsible for engaging the independent registered public accounting firm, reviewing with the independent registered public accounting firm the plans and results of the audit engagement, approving professional services provided by the independent registered public accounting firm and considering the range of audit and non-audit fees.
Compensation, Nominating and Governance Committee
The CNG Committee is comprised of our four independent directors: Messrs. Friedman and Smith and Mses. Goldwasser and Mielle. Ms. Mielle was appointed as the Chair of the CNG Committee on August 24, 2020.
The CNG Committee is responsible for:
• establishing our corporate goals and objectives relevant to the Executive Committee’s compensation, reviewing the Executive Committee’s performance in light of such goals and objectives and evaluating and approving the performance of, and the compensation paid by the Company to, the Executive Committee in light of such goals and objectives;
• reviewing and evaluating the performance of, and recommending to the Board of Directors the compensation of, our executive officers other than the Executive Committee, considering our corporate goals and objectives and evaluating the performance of such executive officers in light of such goals and objectives;
• overseeing the compensation policies and programs of our non-executive officer employees to determine whether such compensation policies and programs are functioning effectively or create any unreasonable risk to the Company, as well as reviewing the appropriateness of the CNG Committee and Lead Director)69July 2013compensation practices to determine if they are reasonably likely to have a material adverse effect on the Company;
Bradley E. Smith59July 2013• reviewing, evaluating and recommending to the Board of Directors any incentive plan or material revision thereto, and administering the same;
• reviewing and approving the disclosure regarding our compensation and benefit matters in our proxy statement and Annual Report;
Class II• identifying, recruiting and recommending to the full Board of Directors qualified candidates for election as directors and recommending a slate of nominees for election as directors at the annual meeting of stockholders;
Michael G. Barnes (Chairman• developing and recommending to the Board of Directors corporate governance guidelines and policies;
• recommending to the Board of Directors compensation for service as directors in accordance with our corporate governance guidelines;
• overseeing the evaluation of the structure, duties, size, membership and functions of the Board of Directors and Executive Chairman)49August 2010its committees and recommending appropriate changes to the Board of Directors; and
John E. Mack (Chairman• establishing procedures to exercise oversight of the Audit Committee)68May 2015evaluation of the Board of Directors and its committees and members (including a self-evaluation).
13

The CNG Committee has the authority to retain, at the Company’s expense, independent legal, accounting and other consultants, advisors and experts that it reasonably determines to be necessary or appropriate to assist the committee in the performance of its responsibilities. For 2021, the CNG Committee engaged Compensation Advisory Partners LLC (“CAP”) as its independent compensation consultant to help advise it on the design of our executive compensation program and the compensation opportunities thereunder. See “Use of Independent Compensation Consultant” below for further details on the services provided by our independent compensation consultant in 2021.
Richard A. Price
Director Compensation
The following table sets forth information regarding the compensation paid to, or earned by our directors, during fiscal 2021:
Director Compensation Fiscal 2021
NameFees Earned or Paid in Cash
($)
Stock
Awards
($)(1)(2)
Total
($)
Michael G. Barnes(3)
———
Paul M. Friedman$115,008$103,848$218,856
Lesley Goldwasser$95,025$129,796$224,821
Jonathan Ilany(3)
———
Randy Maultsby(3)
———
Dominique Mielle$110,008$103,848$213,856
Bradley E. Smith$75,025$129,796$204,821
(1)The number of shares granted is based on the volume weighted average price for the ten trading days prior to the end of the quarter. The grant date closing market price of our common stock for each quarterly payment on each of April 7, 2021, July 6, 2021, October 6, 2021 and January 7, 2022 was $9.93, $8.88, $10.45, and $13.39, respectively.
(2)Represents the grant date fair value of shares granted, as recognized by the Company for financial statement reporting purposes in the fiscal year ended December 31, 2021 in accordance with Accounting Standards Codification 718 — Compensation — Stock Compensation. See Note 19, Stock Based Compensation, to our consolidated financial statements in 2021 Annual Report on Form 10-K.
(3)Messrs. Barnes, Ilany and Maultsby receive no compensation in connection with their service on our Board. The compensation that they receive in their capacity as Executive Chairman, Chief Executive Officer and President, respectively, is included in the Summary Compensation Table below.
Non-Employee Director Compensation Program
In fiscal 2021, each non-employee director was eligible to receive an annual cash retainer of $100,000 plus $100,000 in immediately vested shares of our common stock, both of which are paid quarterly in arrears. Such non-employee directors may elect to receive up to $125,000 of total compensation in the form of immediately vested common stock and the cash compensation payable to such director would be reduced proportionately. The Lead Director received an additional $20,000 annual retainer, the Chair of the Audit Committee receives an additional annual retainer of $15,000 and the Chair of the CNG Committee received an additional annual retainer of $10,000. In addition, we reimburse all directors for reasonable out-of-pocket expenses incurred in connection with their services on our Board of Directors.
14

Principal Executive Officer Pay Ratio
Set forth below is a reasonable estimate of the ratio of annual total compensation of the Company’s principal executive officer (“PEO”) to the median of the annual total compensation of all employees, other than the PEO. The Company views the Executive Committee, consisting of Mr. Barnes, its Executive Chairman, and Mr. Ilany, its Chief Executive Officer, collectively as the Company’s PEO.  
In 2021, we identified the median employee (such person, the “Median Employee”) by using as our consistently applied compensation measure, 2021 gross earnings, as reported on Form W-2 (“W-2 gross earnings”), for all individuals who were employed by the Company and its subsidiaries on December 31, 2021, other than our principal executive officers. We included all employees, whether employed on a full-time, part-time or seasonal basis, and we did not annualize the compensation of any full-time employee who was employed for less than the full 2021 calendar year. We believe that the use of W-2 gross earnings is an appropriate measure by which to determine the Median Employee because it accurately represents annual compensation earned by our employees.

Messrs. Barnes and Ilany had 2021 annual total compensation of $8,877,686 and $9,168,916, respectively, as reflected in the Summary Compensation Table included in this Proxy Statement under “Executive Compensation—Summary Compensation”. Using the same methodology used to calculate Messrs. Barnes and Ilany’s 2021 total compensation in the Summary Compensation Table, our Median Employee’s total compensation for 2021 was $84,137. As a result, we estimate that Messrs. Barnes’s and Ilany’s 2021 annual total compensation was approximately 106 times and 109 times, respectively, that of our Median Employee.
Because the SEC rules for identifying the median of the annual total compensation of our employees and calculating the pay ratio based on the employee’s annual total compensation allow companies to adopt a variety of methodologies, to apply certain exclusions, and to make reasonable estimates and assumptions that reflect their employee populations and compensation practices, the pay ratio reported by other companies may not be comparable to the pay ratio for the Company.
Corporate Governance Guidelines
Our Board of Directors has beenadopted Corporate Governance Guidelines that address significant issues of corporate governance and set forth procedures by which our Board of Directors carries out its responsibilities. Among the areas addressed by the Corporate Governance Guidelines are director qualification standards, director responsibilities, director relationships and access to management and independent advisors, director compensation, director orientation and continuing education, management succession, annual performance evaluation of the Board of Directors and management responsibilities. Our CNG Committee is responsible for assessing and periodically reviewing the adequacy of the Corporate Governance Guidelines and will recommend, as appropriate, proposed changes to the Board of Directors.
Code of Business Conduct and Ethics
Our Board of Directors has adopted a Code of Business Conduct and Ethics that applies to our directors, executive officers (including our principal executive officer and principal financial and accounting officer) and employees, as well as employees of any person or its affiliates that provide services to us. The Code of Business Conduct and Ethics was designed to assist our directors, executive officers and employees, as well as employees of any person or its affiliates that provide services to us, in complying with the law, resolving moral and ethical issues that may arise and in complying with our policies and procedures. Among the areas addressed by the Code of Business Conduct and Ethics are compliance with applicable laws, conflicts of interest, use and protection of our Company’s assets, confidentiality, communications with the public, accounting matters, record keeping and discrimination and harassment.
We intend to satisfy our disclosure obligations under Item 5.05 of Form 8-K related to amendments or waivers of the Code of Business Conduct and Ethics by posting such information on our corporate website.
15


Stockholder Engagement and Communications with our Board of Directors
We have discussions with a variety of our stockholders throughout the year including one-on-one meetings and participation at investor conferences. In addition, we have a process by which stockholders and other parties may communicate with our Board of Directors, our independent directors as a group or our individual directors. Any such communications may be sent to our Board of Directors in writing and should be directed to the Board of Directors, a committee, the independent directors as a group, or an individual director at Tiptree Inc., 299 Park Avenue, 13th Floor, New York, NY, 10171, Attn: Secretary, who will forward all such appropriate communications on to the intended recipient. In addition, stockholder communications can be directed to our Board of Directors, a committee, the independent directors as a group or an individual director by calling our Corporate Governance Hotline at (844) 877-5474. Any such communications may be made anonymously.

Director Attendance at Annual Meetings
Pursuant to our Corporate Governance Guidelines, we expect each member of our Board of Directors since July 2013 and currently serves as Chairmanto attend each annual meeting of stockholders. Last year, all of the Compensation, Nominatingdirectors attended the annual meeting of stockholders.
Identification of Director Candidates
As stated in the CNG Committee Charter, the CNG Committee assists our Board of Directors in identifying and Governancereviewing director candidates to determine whether they qualify for membership on the Board and for recommending to the Board nominees to be considered for election at our annual meeting of stockholders.
In making recommendations to our Board of Directors, the CNG Committee (the “CNG Committee”)considers such factors as it deems appropriate. Though the Company does not have a formal policy addressing diversity, the Board of Directors and Lead Director. Mr. Price was a memberthe CNG Committee believe that diversity is an important attribute of the boardmembers who comprise our Board of Directors and that members should represent an array of backgrounds and experiences and should be capable of articulating a variety of viewpoints. As such, directors should have diversity with respect to background, skills and expertise, industry knowledge and experience. The CNG Committee uses the following general criteria for identifying director candidates:
•Directors should possess senior level management and decision-making experience;
•Directors should have a reputation for integrity and abiding by exemplary standards of Tiptree Financial Partners, LP (“TFP”) from August 2010business and professional conduct;
•Directors should have the commitment and ability to July 2013. From 2008 until 2009, he served as Chairmandevote the time and attention necessary to fulfill their duties and responsibilities to the Company and its stockholders;
•Directors should be highly accomplished in their respective fields, with leadership experience in corporations or other complex organizations, including government, educational and military institutions;
•In addition to satisfying the independence criteria described in the Corporate Governance Guidelines, independent directors should be able to represent all stockholders of the Company;
•Directors who are expected to serve on a committee of the Board of Directors shall satisfy applicable legal requirements and other criteria established by any securities exchange on which our common stock is listed; and
•Directors should have the ability to exercise sound business judgment to provide advice and guidance to the Chief Executive Officer and Executive Chairman with candor.
The foregoing general criteria apply equally to the evaluation of all potential independent and management director nominees, including those individuals recommended by stockholders.
The Board of Directors’ assessment of an individual’s candidacy for CIFG Group, a Bermuda-based holding company with two financial guaranty insurance subsidiaries. From 2005 until 2007, Mr. Price held a varietydirector also includes consideration of roles with Zurich Insurance Company, a global insurance-based financial services provider baseddiversity, age, skills and experience in Zurich, Switzerland. Mr. Price served as a director and chief executive officer of Centre Re, a wholly-owned subsidiary of Zurich Insurance Company, which operated in three non-traditional insurance sectors: finite insurance, financial guaranty insurance and long-term care and disability insurance. Mr. Price also served as chief executive officer of Zurich Capital Markets and as a director of Zurich Bank, Dublin, a major commercial real estate lender in England and Ireland, where he served as chairmanthe context of the auditneeds of the Board of Directors.
Our CNG Committee may solicit and compensation committees. Mr. Price founded CGA Group, Ltd.consider suggestions of our directors or our management regarding possible nominees. Our CNG Committee may also procure the services of outside sources or third parties to assist in 1996, a Bermuda holding company, for which he servedthe identification of director candidates.
16

Our CNG Committee may consider director candidates recommended by our stockholders. Our CNG Committee will apply the same standards in considering candidates submitted by stockholders as chief executive officer until 2001. From 1985 until 1996, Mr. Price served a variety of roles with FGIC, a bond insurance company. Mr. Price led FGIC’s entry into the structured finance marketsit does in 1987 after managing FGIC’s non-vanilla municipal finance business from 1985 until 1987. From 1970 until 1985, Mr. Price worked in banking for Chemical Bank & Bankers Trust. Mr. Price received his Bachelor of Science degree in engineering from Cornell University and his Master’s of Business Administration from the Wharton School of Business.
Mr. Price was selected and qualified to serve as a memberevaluating candidates submitted by members of our Board of Directors becauseor our management. Any recommendations by stockholders should follow the procedures outlined under “Additional Information — Stockholder Proposals” in this proxy statement and in our Bylaws.
Executive Sessions of his extensive, senior experience inIndependent Directors
In accordance with our Corporate Governance Guidelines, the specialty insurance industry and the structured finance markets and his prior board experience.
Bradley E. Smith has been a member ofindependent directors serving on our Board of Directors since July 2013. Mr. Smith was a memberare given an opportunity at each meeting to meet in executive session without the presence of the boardany directors or other persons who are part of our management. Our executive sessions were chaired by our Lead Director, Ms. Goldwasser. Interested parties may communicate directly with our Lead Director or our independent directors of TFP from June 2007 to July 2013. He is the founder of Kahala Capital Advisors LLC, a private investment firm, and of Kahala Aviation Ltd. a commercial aircraft leasing company. Prior to Kahala Capital, Mr. Smith worked for almost 20 years in banking in New York and Asia. He was employed from 1995 until 2000 at Bear Stearns where he started that company’s credit derivatives businesses in New York; and later as a Senior Managing Director, based in Tokyo managinggroup through the firm’s fixed income and derivative businesses. Before Bear Stearns, Mr. Smith spent 10 yearsprocess set forth above under “Communications with Bankers Trust Company as a syndicate manager in its loan syndications group, where he was responsible for the syndication of some of the largest leveraged loan financings ever completed. Afterwards, he transferred to Tokyo and Hong Kong, where he was involved in BT’s credit trading businesses in Asia. In his last position at Bankers Trust, Mr. Smith was one of the founders of that bank’s credit derivatives business. He is currently on the board of Tricadia Credit Strategies, Ltd. Mr. Smith holds a B.A. from St. Joseph’s University and an M.B.A. from the American Graduate School of International Management.
Mr. Smith was selected and qualified to serve on Tiptree’s board due to his knowledge as a private investor and entrepreneur, experience involving large complex financial transactions and his extensive international relationships.
Michael G. Barnes has been a member of our Board of Directors.”
Current Board Leadership Structure
Our Board of Directors since August 2010, and he currently serves asis led by Michael G. Barnes, the Chairman of our Board of Directors, and our Executive Chairman.
Because the Chairman of the Board of Directors is not independent, the Board of Directors appointed Ms. Goldwasser to serve as wellthe Company’s Lead Director and preside at executive sessions of the independent directors and at meetings of the Board of Directors when the Chairman is not present.
To help ensure that the Board of Directors carries out its oversight responsibilities, our Corporate Governance Guidelines require the Board of Directors as a whole to maintain independence from management. Pursuant to the Corporate Governance Guidelines, a majority of the Board of Directors must be independent. As of the date hereof, four of our current seven directors have been determined to be independent.
Board’s Role in Risk Oversight
Our Board of Directors oversees our business in general, including risk management and performance of the Executive Chairman, of our Company and is a member of


the Tiptree management executive committee. He has been the Chairman of TFP since its inception in 2007 and served as the Chief Executive Officer and other members of TFP from 2007 until June 2012. Mr. Barnes has been Executive Chairman of Tiptree Operating Company, LLC (“Operating Company”) since July 1, 2013. Mr. Barnes is a founding partner and currently Managing Partner and Co-Chief Investment Officer of Tricadia Holdings, L.P. (“Tricadia”) and its affiliated companies, which are privately held and provide investmentsenior management, services. Prior to assure that the formation of Tricadia in 2003, Mr. Barnes spent two years as Head of Structured Credit Arbitrage within UBS Principal Finance LLC, a wholly owned subsidiary of UBS Warburg, which conducted proprietary trading on behalflong-term interests of the firm. Mr. Barnes joined UBS in 2000 as part of the merger between UBS and PaineWebber Inc. Prior to joining UBS, Mr. Barnes was a Managing Director and Global Head of the Structured Credit Products Group of PaineWebber. Prior to joining PaineWebber in 1999, he spent 12 years at Bear Stearns, the last five of which he was head of their Structured Transactions Group. Mr. Barnes received his A.B. from Columbia College.
Mr. Barnes was selected and qualified to serve as a memberstockholders are being served. Each committee of our Board of Directors becauseis also responsible for reviewing the risk exposure related to such committee’s areas of his extensive senior level experience in the investment management industry, including with respectresponsibility and providing input to the management of credit and real estate assets.

John E. Mack has been a member of our Board of Director since May 2015 and currently serves as Chairman of the Audit Committee. Mr. Mack has over 40 years of international banking and financial business management experience. Mr. Mack is currently a member of the board of directors of Tiptree, Medley Capital Corporation, Incapital Holdings LLC, Searchlight Minerals Corp and GlobalMin Ventures Inc.  From January 2010 to March 2015, Mr. Mack was Vice Chairman and a director of Islandsbanki hf located in Reykjavik, Iceland. From November 2011 through December 2013, Mr. Mack was a member of the board of directors of Residential Capital LLC. From November 2002 through September 2005, Mr. Mack served as Senior Managing Executive Officer and Chief Financial Officer of Shinsei Bank, Limited of Tokyo, Japan. Prior to joining Shinsei Bank and for more than twenty-five years, Mr. Mack served in senior management positions at Bank of Americaon such risks.
Management and its predecessor companies, including twelve years as Corporate Treasurer of NationsBank Corporation and NCNB Corporation. Mr. Mack holds an MBA from the University of Virginia, Darden School of Business and received his bachelor’s degree in Economics from Davidson College.

Mr. Mack was selected and qualified to serve as a member of our Board of Directors becausehave a process to identify, analyze, manage and report all significant risks facing us. Our Executive Chairman and Chief Executive Officers will regularly report to the Board of his experience inDirectors on significant risks facing us, including legal, financial, operational and strategic risks. The Audit Committee reviews with senior management positions at large financial institutions and his extensive experience in finance, accounting and regulatory issues. In addition, his tenure in the financial services industry and service as a director of both public and private companies provide industry-specific knowledge and expertise to our Board of Directors.
EXECUTIVE OFFICERS
Set forth below is the background information regarding each of our executive officers as of April 27, 2016, other than Mr. Ilany, whose biography is above under “Information Regarding Nominees for Election” and Mr. Barnes, whose biography is above under “Continuing Directors”.
Sandra Bell, age 59, has been our Chief Financial Officer since July 2015. Ms. Bell brings over 30 years of business experience in the financial services and energy industries, both as a public company Chief Financial Officer and as an investment banker. Most recently, Ms. Bell served as Chief Financial Officer of Prospect Mortgage, LLC (“Prospect”), a private equity owned mortgage originator and servicer, overseeing all financial activities, including strategic planning, treasury, financial reporting, bank and rating agency relationships and investor relations. Prior to joining Prospect, from 2008 to 2011, Ms. Bell served as Chief Financial Officer of PHH Corporation (“PHH”), a publicly traded, multi-divisional financial services company engaged in the private label mortgage services and fleet management businesses. While at PHH, her responsibilities included treasury, cash management and banking relationships, strategic planning, budgeting and forecasting, investor relations, accounting and public reporting, audit and tax. Prior to PHH, Ms. Bell served as Executive Vice President and Chief Financial Officer of the Federal Home Loan Bank of Cincinnati, where Ms. Bell managed its development, profitability and risk of its core business lines. She also led the strategic financial management and reporting functions, including SEC reporting; treasury, including funding and capital and risk management; credit services, including the lending and credit risk management functions; and management of a whole loan mortgage portfolio. Prior to assuming her position at the Federal Home Loan Bank, Ms. Bell had been a Managing Director at Deutsche Bank Securities, where she had been employed for 13 years. Ms. Bell received a Bachelor of Arts degree in Economics from The Ohio State University


and a Masters in Business Administration from Harvard Business School.
Julia Wyatt, age 58, has been our Chief Operating Officer since January 2015. Previously, Ms. Wyatt was our Chief Financial Officer and the Chief Financial Officer of the Operating Company from July 2013 to January 2015. Ms. Wyatt was also the Chief Financial Officer of Tricadia from 2005 to March 2016. Prior to joining Tricadia in 2005, Ms. Wyatt was the Chief Financial Officer of Havell Capital Management (“HCM”) from 1996 to 2005, which is a specialized investment management firm dedicated to managing funds in fixed income markets. During her tenure with HCM, Ms. Wyatt was responsible for all non-investmentsignificant risks related aspects of the firm, including financial, legal, regulatory and client services. Prior to HCM, from 1992 to 1996, Ms. Wyatt was a senior member of the fixed income management group with Neuberger Berman. Previously, from 1987 to 1991, she was employed by Morgan Grenfell Capital Management, where she was the Treasurer and Director of Client Services. Ms. Wyatt was with Deloitte & Touche from 1980 to 1988, spending the last two years in the Executive Office Research Department as a Senior Manager. Ms. Wyatt has a B.S. in Accounting from the University of Utah.
Timothy Schott, age 46, was appointed our Principal Accounting Officer effective April 4, 2016. Prior to joining Tiptree, Mr. Schott was at Lazard Ltd., a financial advisory and asset management firm, since 2011, as the Director of Accounting Policy for Global Finance, where he led the oversight of compliance with U.S. GAAP, including SEC reporting and approval of the accounting for significant and complex transactions. Prior to Lazard Ltd., Mr. Schott was a partner at Deloitte & Touche Financial Accounting and Reporting Services since 2007, providing accounting consulting services to clients in a variety of industries, with emphasis on the financial services industry, on matters pertaining to the accounting, reporting and valuation for complex transactions. Prior to joining Deloitte’s advisory business in 2004, Mr. Schott spent 11 years as an auditor at Deloitte. Mr. Schott is a Certified Public Accountant in New York. Mr. Schott received his B.S. in accounting at Fairfield University.
Patrick Huvane, age 47, has been our Chief Accounting Officer and the Chief Accounting Officer of the Operating Company since August 2013. He was our Principal Accounting Officer and the Principal Accounting Officer of the Operating Company from February 2013 to August 2013, and Controller of TFP since November 2007. Mr. Huvane is employed by Mariner Investment Group LLC (“Mariner”) and provides services to the Company and periodically reports to the Operating Company through an Administrative Services Agreement between BackOffice Services Group, Inc., an affiliateBoard of Mariner,Directors on such risks.
In addition, pursuant to its charter, the Audit Committee is responsible for reviewing and discussing the Operating Company. Prior to joining Mariner in 2007, Mr. Huvane was Controller at Axon Financial Services, Inc. (“Axon”) from 2006 to 2007. ForCompany’s business risk management process, including the five years prior to joining Axon, Mr. Huvane was employed at Fletcher Asset Management, Inc. (“Fletcher”). During his tenure with Fletcher, Mr. Huvane held positions of increasing responsibility, including as Chief Financial Officerquality and Chief Compliance Officer. Prior to that date, Mr. Huvane also was at Credit Suisse and Sumitomo Bank. He began his career as an auditor at Ernst & Young in 1990. Mr. Huvane was a part-time adjunct faculty member of Manhattan College’s Department of Economics & Finance from 2008 to 2009. Mr. Huvane is a Certified Public Accountant in New York and is also a CFA charterholder. Mr. Huvane has a B.S. in Accounting from Manhattan College and an M.B.A. in Finance from New York University’s Leonard N. Stern School of Business.
Neil C. Rifkind, age 49, has been our Vice President, General Counsel and Secretary and the Vice President, General Counsel and Secretary of the Operating Company since July 2013. From 2011 until July 2013, Mr. Rifkind was Special Counsel at the law firm of Schulte Roth & Zabel LLP, specializing in mergers and acquisitions and securities law. From 2006 through 2010, he was an associate at Schulte Roth & Zabel LLP. From 1998 until 2006, Mr. Rifkind was an associate at the law firm of Fried, Frank, Harris, Shriver & Jacobson LLP. Mr. Rifkind has a J.D. from Boston University School of Law, an M.A. in Philosophy from the University of Toronto and an A.B. in Philosophy from the University of Chicago.
CORPORATE GOVERNANCE MATTERS
This section of our proxy statement contains information about our corporate governance policies and practices. You can visit the governance documents section of our corporate website at http://www.tiptreefinancial.com to view or to obtain copiesintegrity of the Company’s Bylaws, Charter,financial statements, and accounting and reporting processes, the Company’s compliance with legal and regulatory requirements, the independent registered public accounting firm’s qualifications and independence, and the performance of the Company’s internal audit function. Furthermore, the Audit Committee evaluates key financial statement issues and risks, their impact or potential effect on reported financial information and the process used by management to address such matters. At each Audit Committee meeting, management briefs the committee on the current business and financial position of the Company, as well as such items as internal audits and independent audits.
17


Compensation Risk Assessment
The CNG Committee Charter, Auditassessed our compensation policies and practices to evaluate whether they create risks that are reasonably likely to have a material adverse effect on the Company. Based on its assessment, the CNG Committee Charter, Codeconcluded that the Company’s compensation policies and practices, in conjunction with the Company’s existing processes and controls, do not create incentives to take risks that are reasonably likely to have a material adverse effect on the Company.
CNG Committee Interlocks and Insider Participation
The following non-employee directors are the current members of Business Conductthe CNG Committee of the Board of Directors: Messrs. Friedman and Ethics, CodeSmith and Mses. Goldwasser and Mielle. During 2021, none of Ethical Conduct and Corporate Governance Guidelines. The information found on,the Company’s executive officers served as a director or accessible through, our website is not incorporated into, and


does not form a partmember of this proxy statement orthe corporate governance committee of any other reportentity whose executive officers served on the Company’s Board of Directors or document we file with or furnish to the SEC. You may also obtain, freeCNG Committee.

Prohibition of charge, a copy of our Bylaws, Charter, CNG Committee Charter, Audit Committee Charter, Code of Business ConductHedging and Ethics, Code of Ethical Conduct, Corporate Governance Guidelines andPledging Transactions
Our Tiptree Inc. Securities Trading Policy by directing your request(“Insider Trading Policy”) prohibits short sales of and option trading on Tiptree stock and prohibits our directors and officers, other employees of Tiptree subject to the Insider Trading Policy and their respective designees from engaging in writinghedging transactions, such as (but not limited to) zero-cost collars, equity swaps, exchange funds and forward sale contracts, that may allow such individual to continue to own Tiptree Financial Inc., 780 Third Avenue, 21st Floor, New York, NY, 10017, Attn: Secretarysecurities without the full risks and rewards of ownership.  Our Insider Trading Policy also prohibits holding Tiptree securities in a margin account or by calling our corporate number at (212) 446-1400.otherwise pledging Tiptree securities as collateral for a loan.

The Board of Directors and its Committees

Our business and affairs are overseen by our Board of Directors pursuant to the Maryland General Corporation Law (the “MGCL”) and our Charter and Bylaws. Members of the Board of Directors are kept informed of the Company’s business by participating in Board and Committeecommittee meetings, by reviewing materials provided to them and through discussions with the Chairman and CEO and with key members of management.

The Company has elected to be subject to Section 3-804(c) of the MGCL (the “Opt-In”), which is a common practice among Maryland corporations with classified boards. As a result of the Opt-In, the Board has the exclusive power to fill vacancies on the Board, and any director elected by the Board to fill a vacancy will hold office for the remainder of the full term of the class of directors in which the vacancy occurred and until his or her successor is elected and qualified.

The average age of our directors, including our director nominees, is 60.359 years. The average tenure of our directors, including our director nominees as of the 20162022 Annual Meeting, is expected to be approximately 3six years.

Our Board of Directors presently consists of sixseven members: Michael G. Barnes, Paul M. Friedman, Lesley Goldwasser, Jonathan Ilany, John E. Mack, Richard A. PriceRandy Maultsby, Dominique Mielle and Bradley E. Smith. The Board of Directors has affirmatively determined that Messrs. Price, MackFriedman and Smith and Ms.Mses. Goldwasser and Mielle are independent as that term is defined in NASDAQ MarketplaceNasdaq Stock Market Rules and SEC regulations.

The Board of Directors currently has two standing committees: an Audit Committee and a Compensation, Nominating and Governance Committee (the “CNG Committee”).CNG Committee.

During fiscal 2015,2021, our Board of Directors held eightnine meetings, the Audit Committee held fiveeight meetings and the CNG Committee held sixeight formal meetings and several informal discussions among the members of the CNG Committee and its independent compensation consultant. All of our directors during fiscal 20152021 attended at least 75% of the combined totalaggregate number of meetings of our Board of Directors and the committeeseach committee of the Board of Directors on which they served if any, during fiscal 2015.2021.
Audit Committee
Our Board of Directors has established an audit committee that meets the definition provided by Section 3(a)(58)(A) of the Securities Exchange Act of 1934, as amended (the “Exchange Act”). Until the Annual Meeting,Currently the Audit Committee will beis comprised of our four independent directors: Messrs. Mack, Price,Friedman and Smith and Ms. Goldwasser.Mses. Goldwasser and Mielle. The current Audit Committee members satisfy the definition of independence set forth in the NASDAQ MarketplaceNasdaq Stock Market Rules and Rule 10A-3 under the Exchange Act. Mr. Mack isFriedman was appointed as the Chairman of the Audit Committee andon August 24, 2020. He was determined by our Board of Directors to be an “audit committee financial expert” as that term is defined in the Exchange Act.
The Audit Committee assists the Board of Directors in overseeing:
12

our accounting and financial reporting processes;
the quality and integrity and audits of our consolidated financial statements, and accounting and reporting processes;
our compliance with legal and regulatory requirements;
the qualifications and independence of our independent registered public accounting firm; and
The Audit Committee is responsible for overseeing:
• our accounting and financial reporting processes;
• the quality and integrity and audits of our consolidated financial statements, and accounting and reporting processes;
• our compliance with legal and regulatory requirements;
• the qualifications and independence of our independent registered public accounting firm; and
• the performance of our independent registered public accounting firm and any internal auditors.
The Audit Committee is also responsible for engaging the independent registered public accounting firm, reviewing with the independent registered public accounting firm the plans and results of the audit engagement, approving professional services provided by the independent registered public accounting firm and considering the range of audit and non-audit fees.
Compensation, Nominating and Governance Committee


Until the Annual Meeting, theThe CNG Committee will beis comprised of our four independent directors: Messrs. Mack, PriceFriedman and Smith and Mses. Goldwasser and Mielle. Ms. Goldwasser. Mr. Price has been ChairmanMielle was appointed as the Chair of the CNG Committee since July 2013.on August 24, 2020.
The CNG Committee is responsible for:
establishing our corporate goals and objectives relevant to the Chief Executive Officer’s compensation, reviewing the Chief Executive Officer’s performance in light of such goals and objectives and evaluating and approving the performance of, and the compensation paid by the Company to, the Chief Executive Officer in light of such goals and objectives;
reviewing and evaluating the performance of, and recommending to the Board of Directors the compensation of, our executive officers other than our Chief Executive Officer, considering our corporate goals and objectives and evaluating the performance of such executive officers in light of such goals and objectives;
overseeing the compensation policies and programs of our non-executive officer employees to determine whether such compensation policies and programs are functioning effectively and do not create any unreasonable risk to the Company, as well as reviewing the appropriateness of the compensation practices to determine if they are reasonably likely to have a material adverse effect on the Company;
reviewing, evaluating and recommending to the Board of Directors any incentive plan or material revision thereto, and administering the same;
reviewing and approving the disclosure regarding our compensation and benefit matters in our proxy statement and Annual Report;
identifying, recruiting and recommending to the full Board of Directors qualified candidates for election as directors and recommending a slate of nominees for election as directors at the annual meeting of stockholders;
developing and recommending to the Board of Directors corporate governance guidelines and policies;
recommending to the Board of Directors compensation for service as directors in accordance with our corporate governance guidelines;
overseeing the evaluation of the structure, duties, size, membership and functions of the Board of Directors and its committees and recommending appropriate changes to the Board of Directors; and
The CNG Committee is responsible for:
• establishing our corporate goals and objectives relevant to the Executive Committee’s compensation, reviewing the Executive Committee’s performance in light of such goals and objectives and evaluating and approving the performance of, and the compensation paid by the Company to, the Executive Committee in light of such goals and objectives;
• reviewing and evaluating the performance of, and recommending to the Board of Directors the compensation of, our executive officers other than the Executive Committee, considering our corporate goals and objectives and evaluating the performance of such executive officers in light of such goals and objectives;
• overseeing the compensation policies and programs of our non-executive officer employees to determine whether such compensation policies and programs are functioning effectively or create any unreasonable risk to the Company, as well as reviewing the appropriateness of the compensation practices to determine if they are reasonably likely to have a material adverse effect on the Company;
• reviewing, evaluating and recommending to the Board of Directors any incentive plan or material revision thereto, and administering the same;
• reviewing and approving the disclosure regarding our compensation and benefit matters in our proxy statement and Annual Report;
• identifying, recruiting and recommending to the full Board of Directors qualified candidates for election as directors and recommending a slate of nominees for election as directors at the annual meeting of stockholders;
• developing and recommending to the Board of Directors corporate governance guidelines and policies;
• recommending to the Board of Directors compensation for service as directors in accordance with our corporate governance guidelines;
• overseeing the evaluation of the structure, duties, size, membership and functions of the Board of Directors and its committees and recommending appropriate changes to the Board of Directors; and
• establishing procedures to exercise oversight of the evaluation of the Board of Directors and its committees and members (including a self-evaluation).
13

The CNG Committee has the authority to retain, at the Company’s expense, independent legal, accounting and other consultants, advisors and experts that it reasonably determines to be necessary or appropriate to assist the committee in the performance of its responsibilities. In 2015,For 2021, the CNG Committee engaged Compensation Advisory Partners LLC (“CAP”) as its independent compensation consultant to help advise it on the design and amount of our executive compensation.compensation program and the compensation opportunities thereunder. See “Use of Independent Compensation Consultant” below for further details on the services provided by our independent compensation consultant in 2021.

Director Compensation
The following table sets forth information regarding the compensation paid to, and the compensation expense we recognized, with respect toor earned by our Board of Directorsdirectors, during fiscal 2015:2021:


Director Compensation Fiscal 2015 (1)(2)2021
Name 
Fees Earned or
Paid in
Cash
($)
 
Stock
Awards
($)
 
Total
($)
Michael G. Barnes(3)
 $—
 $—
 $—
Lesley Goldwasser $75,005
 $33,025
 $108,030
William A. Houlihan(4)
 $32,548
 $13,849
 $46,397
Jonathan Ilany(5)
 $—
 $—
 $—
Geoffrey N. Kauffman(6)
 $—
 $—
 $—
John E. Mack(7)
 $57,119
 $19,916
 $77,035
Richard A. Price $85,005
 $33,025
 $118,030
Bradley E. Smith $75,005
 $33,025
 $108,030
NameFees Earned or Paid in Cash
($)
Stock
Awards
($)(1)(2)
Total
($)
Michael G. Barnes(3)
———
Paul M. Friedman$115,008$103,848$218,856
Lesley Goldwasser$95,025$129,796$224,821
Jonathan Ilany(3)
———
Randy Maultsby(3)
———
Dominique Mielle$110,008$103,848$213,856
Bradley E. Smith$75,025$129,796$204,821
 
(1)
Amounts
(1)The number of shares granted is based on the volume weighted average price for the ten trading days prior to the end of the quarter. The grant date closing market price of our common stock for each quarterly payment on each of April 7, 2021, July 6, 2021, October 6, 2021 and January 7, 2022 was $9.93, $8.88, $10.45, and $13.39, respectively.
(2)Represents the grant date fair value of shares granted, as recognized by the Company for financial statement reporting purposes in the fiscal year ended December 31, 2021 in accordance with Accounting Standards Codification 718 — Compensation — Stock Compensation. See Note 19, Stock Based Compensation, to our consolidated financial statements in 2021 Annual Report on Form 10-K.
(3)Messrs. Barnes, Ilany and Maultsby receive no compensation in connection with their service on our Board. The compensation that they receive in their capacity as Executive Chairman, Chief Executive Officer and President, respectively, is included in the Summary Compensation Table below.
Non-Employee Director Compensation Program
In fiscal 2021, each non-employee director was eligible to receive an annual cash retainer of $100,000 plus $100,000 in immediately vested shares of our common stock, both of which are paid quarterly in arrears. Such non-employee directors may elect to receive up to $125,000 of total compensation in the form of immediately vested common stock and the cash compensation payable to such director would be reduced proportionately. The Lead Director received an additional $20,000 annual retainer, the Company for financial statement reporting purposes in the fiscal year ended December 31, 2015 in accordance with Accounting Standards Codification 718 — Compensation — Stock Compensation. See Note 21 to the consolidated financial statements contained in the 2015 10-K. In accordance with SEC rules, estimates of forfeitures related to service-based conditions have been disregarded. In fiscal 2015, each director other than Messrs. Barnes and Ilany and former director, Mr. Kauffman, received an annual retainer of $50,000, plus $6,250 per quarter for attending each quarterly meeting (for total meeting fees of $25,000 per year), plus $35,000 in immediately vested shares of our common stock. Each independent director may elect to receive up to $70,000 of the total compensation in the form of immediately vested shares of our common stock rather than cash. The annual retainer payable to our independent directors is payable quarterly in arrears. These shares are granted in arrears with the number of shares based on the volume weighted average price for the ten trading days prior to the end of the quarter. The grant date fair market value of our common stock for each of the fiscal quarters in 2015 were $6.88, $7.01, $6.16 and $5.67, respectively.
(2)For a list of beneficial ownership of our Class A common stock held by our directors as of March 31, 2016, see “Security Ownership of Certain Beneficial Owners and Management” below.
(3)Mr. Barnes receives no annual retainer in connection with his service on our Board.
(3)Mr. Houlihan’s tenure as a director ended on May 12, 2015.
(4)Mr. Ilany receives no annual retainer in connection with his service on our Board.
(5)Mr. Kauffman’s tenure as a director ended on November 10, 2015; Mr. Kauffman received no annual retainer in connection with his service on our Board.
(6)Mr. Mack joined the Board effective May 12, 2015.

The Chair of the Audit Committee receives an additional annual retainer of $15,000 and the chairChair of the CNG Committee receivesreceived an additional annual retainer of $10,000. In addition, we reimburse all directors for reasonable out-of-pocket expenses incurred in connection with their services on our Board of Directors.
14

Principal Executive Officer Pay Ratio
Set forth below is a reasonable estimate of the ratio of annual total compensation of the Company’s principal executive officer (“PEO”) to the median of the annual total compensation of all employees, other than the PEO. The Company views the Executive Committee, consisting of Mr. Barnes, its Executive Chairman, and Mr. Ilany, its Chief Executive Officer, collectively as the Company’s PEO.  
In 2021, we identified the median employee (such person, the “Median Employee”) by using as our consistently applied compensation measure, 2021 gross earnings, as reported on Form W-2 (“W-2 gross earnings”), for all individuals who were employed by the Company and its subsidiaries on December 31, 2021, other than our principal executive officers. We included all employees, whether employed on a full-time, part-time or seasonal basis, and we did not annualize the compensation of any full-time employee who was employed for less than the full 2021 calendar year. We believe that the use of W-2 gross earnings is an appropriate measure by which to determine the Median Employee because it accurately represents annual compensation earned by our employees.

Messrs. Barnes and Ilany had 2021 annual total compensation of $8,877,686 and $9,168,916, respectively, as reflected in the Summary Compensation Table included in this Proxy Statement under “Executive Compensation—Summary Compensation”. Using the same methodology used to calculate Messrs. Barnes and Ilany’s 2021 total compensation in the Summary Compensation Table, our Median Employee’s total compensation for 2021 was $84,137. As a result, we estimate that Messrs. Barnes’s and Ilany’s 2021 annual total compensation was approximately 106 times and 109 times, respectively, that of our Median Employee.
Because the SEC rules for identifying the median of the annual total compensation of our employees and calculating the pay ratio based on the employee’s annual total compensation allow companies to adopt a variety of methodologies, to apply certain exclusions, and to make reasonable estimates and assumptions that reflect their employee populations and compensation practices, the pay ratio reported by other companies may not be comparable to the pay ratio for the Company.
Corporate Governance Guidelines
Our Board of Directors has adopted Corporate Governance Guidelines that address significant issues of corporate governance and set forth procedures by which our Board of Directors carries out its responsibilities. Among the areas addressed by the Corporate Governance Guidelines are director qualification standards, director responsibilities, director relationships and access to management and independent advisors, director compensation, director orientation and continuing education, management succession, annual performance evaluation of the Board of Directors and management responsibilities. Our CNG Committee is responsible for assessing and periodically reviewing the adequacy of the Corporate Governance Guidelines and will recommend, as appropriate, proposed changes to the Board of Directors.
Code of Business Conduct and Ethics and Code of Ethical Conduct
Our Board of Directors has adopted a Code of Business Conduct and Ethics that applies to our directors, executive officers (including our principal executive officer and principal financial and accounting officer) and employees, as well as employees of any person or its affiliates that provide services to us. The Code of Business Conduct and Ethics was designed to assist our directors, executive officers and employees, as well as employees of any person or its affiliates that provide services to us, in complying with the law, resolving moral and ethical issues that may arise and in complying with our policies and procedures. Among the areas addressed by the Code of Business Conduct and Ethics are compliance with applicable laws, conflicts of interest, use and protection of our


Company’s assets, confidentiality, communications with the public, accounting matters, record keeping and discrimination and harassment. In addition, we have a Code of Ethical Conduct that applies to our senior officers and financial managers. The Code of Ethical Conduct provides principles to which senior officers and financial managers are expected to adhere and advocate, rules regarding individual and peer responsibilities, and responsibilities to other employees, us, the public and other stockholders. Like the Code of Business Conduct and Ethics, it is designed to assist the senior officers and financial managers comply with the law and resolve moral and ethical issues that may arise.
We intend to satisfy our disclosure obligations under Item 5.05 of Form 8-K related to amendments or waivers of the Code of Business Conduct and Ethics by posting such information on our corporate website.
15


Stockholder Engagement and Communications with our Board of Directors
We have discussions with a variety of our stockholders throughout the year including one-on-one meetings and participation at investor conferences. In addition, we have a process by which stockholders and/orand other parties may communicate with our Board of Directors, our independent directors as a group or our individual directors. Any such communications may be sent to our Board of Directors in writing and should be directed to the Board of Directors, a committee, the independent directors as a group, or an individual director at Tiptree Financial Inc., 780 Third299 Park Avenue, 21st13th Floor, New York, NY, 10017,10171, Attn: Secretary, who will forward all such appropriate communications on to the intended recipient. In addition, stockholder communications can be directed to our Board of Directors, a committee, the independent directors as a group or an individual director by calling our Corporate Governance Hotline at (844) 877-5474. Any such communications may be made anonymously.

Director Attendance at Annual Meetings
Pursuant to our Corporate Governance Guidelines, we expect each member of our Board of Directors to attend each annual meeting of stockholders. Last year, all of the then six directors attended the annual meeting of stockholders.
Identification of Director Candidates
As stated in the CNG Committee Charter, the CNG Committee assists our Board of Directors in identifying and reviewing director candidates to determine whether they qualify for membership on the Board and for recommending to the Board nominees to be considered for election at our annual meeting of stockholders.
In making recommendations to our Board of Directors, the CNG Committee considers such factors as it deems appropriate. Though the Company does not have a formal policy addressing diversity, the Board of Directors and the CNG Committee believe that diversity is an important attribute of the members who comprise our Board of Directors and that members should represent an array of backgrounds and experiences and should be capable of articulating a variety of viewpoints. As such, directors should have diversity with respect to background, skills and expertise, industry knowledge and experience. The CNG Committee uses the following general criteria for identifying director candidates:
•Directors should possess senior level management and decision-making experience;
•Directors should have a reputation for integrity and abiding by exemplary standards of business and professional conduct;
•Directors should have the commitment and ability to devote the time and attention necessary to fulfill their duties and responsibilities to the Company and its stockholders;
•Directors should be highly accomplished in their respective fields, with leadership experience in corporations or other complex organizations, including government, educational and military institutions;
•In addition to satisfying the independence criteria described in the Corporate Governance Guidelines, independent directors should be able to represent all stockholders of the Company;
•Directors who are expected to serve on a committee of the Board of Directors shall satisfy applicable legal requirements and other criteria established by any securities exchange on which our common stock is listed; and
•Directors should have the ability to exercise sound business judgment to provide advice and guidance to the Chief Executive Officer and Executive Chairman with candor.


The foregoing general criteria apply equally to the evaluation of all potential independent and management director nominees, including those individuals recommended by stockholders.
The Board of Director’sDirectors’ assessment of aan individual’s candidacy for director candidate’s qualifications also includes consideration of diversity, age, skills and experience in the context of the needs of the Board of Directors.
Our CNG Committee may solicit and consider suggestions of our directors TFP or its affiliates or our management regarding possible nominees. Our CNG Committee may also procure the services of outside sources or third parties to assist in the identification of director candidates.
16

Our CNG Committee may consider director candidates recommended by our stockholders. Our CNG Committee will apply the same standards in considering candidates submitted by stockholders as it does in evaluating candidates submitted by members of our Board of Directors TFP or its affiliates or our management. Any recommendations by stockholders should follow the procedures outlined under “Additional Information — Stockholder Proposals” in this proxy statement and in our Bylaws.
Executive Sessions of Independent Directors
In accordance with our Corporate Governance Guidelines, the independent directors serving on our Board of Directors are given an opportunity at each meeting to meet in executive session without the presence of any directors or other persons who are part of our management. Our executive sessions were chaired by our Lead Director, who was Mr. Houlihan prior to March 26, 2015 and was Mr. Price thereafter.Ms. Goldwasser. Interested parties may communicate directly with our Lead Director or our independent directors as a group through the process set forth above under “Communications with our Board of Directors.”
Current Board Leadership Structure
Our Board of Directors is led by Michael G. Barnes, the Chairman of our Board of Directors, and our Executive Chairman.
Because the Chairman of the Board of Directors is not independent, the Board of Directors appointed Mr. PriceMs. Goldwasser to serve as the Company’s Lead Director and preside at executive sessions of the independent directors and at meetings of the Board of Directors when the Chairman is not present.
To help ensure that the Board of Directors carries out its oversight responsibilities, our Corporate Governance Guidelines require the Board of Directors as a whole to maintain independence from management. Pursuant to the Corporate Governance Guidelines, a majority of the Board of Directors must be independent. As of the date hereof, four of our current sixseven directors have been determined to be independent.
Board’s Role in Risk Oversight
Our Board of Directors oversees our business in general, including risk management and performance of the Executive Chairman, Chief Executive Officer and other members of senior management, to assure that the long-term interests of the stockholders are being served. Each committee of our Board of Directors is also responsible for reviewing the risk exposure related to such committee’s areas of responsibility and providing input to senior management on such risks.
Management and our Board of Directors have a process to identify, analyze, manage and report all significant risks facing us. Our Executive Chairman and Chief Executive Officers will regularly report to the Board of Directors on significant risks facing us, including legal, financial, operational and strategic risks. The Audit Committee reviews with senior management significant risks related to the Company and periodically reports to the Board of Directors on such risks.
In addition, pursuant to its charter, the Audit Committee is responsible for reviewing and discussing the Company’s business risk management process, including the quality and integrity of the Company’s financial statements, and accounting and reporting processes, the Company’s compliance with legal and regulatory requirements, the independent registered public accounting firm’s qualifications and independence, and the


performance of the Company’s internal audit function. Furthermore, the Audit Committee evaluates key financial statement issues and risks, their impact or potential effect on reported financial information and the process used by management to address such matters. At each Audit Committee meeting, management briefs the committee on the current business and financial position of the Company, as well as such items as internal audits and independent audits.
17


Compensation Risk Assessment
The CNG Committee assessed our compensation policies and practices to evaluate whether they create risks that are reasonably likely to have a material adverse effect on the Company. Based on its assessment, the CNG Committee concluded that the Company’s compensation policies and practices, in conjunction with the Company’s existing processes and controls, do not create incentives to take risks that are reasonably likely to have a material adverse effect on the Company.
CNG Committee Interlocks and Insider Participation
The following non-employee directors are the current members of the CNG Committee of the Board of Directors: Messrs. Price, MackFriedman and Smith and Ms. Goldwasser. Until he ceased being a director on May 12, 2015, Mr. Houlihan was a member of the CNG Committee.Mses. Goldwasser and Mielle. During 2015,2021, none of the Company’s executive officers served as a director or member of the corporate governance committee of any other entity whose executive officers served on the Company’s Board of Directors or CNG Committee.

AUDIT COMMITTEE REPORT
Prohibition of Hedging and Pledging Transactions
Our Tiptree Inc. Securities Trading Policy (“Insider Trading Policy”) prohibits short sales of and option trading on Tiptree stock and prohibits our directors and officers, other employees of Tiptree subject to the Insider Trading Policy and their respective designees from engaging in hedging transactions, such as (but not limited to) zero-cost collars, equity swaps, exchange funds and forward sale contracts, that may allow such individual to continue to own Tiptree securities without the full risks and rewards of ownership.  Our Insider Trading Policy also prohibits holding Tiptree securities in a margin account or otherwise pledging Tiptree securities as collateral for a loan.

CONTINUING DIRECTORS
The Audit Committee oversees our financial reporting process on behalffollowing table and biographical descriptions set forth certain information, as of March 31, 2022, with respect to each continuing director.
NameAgeDirector Since
Class I
Paul M. Friedman (Chairman of the Audit Committee)66August 2016
Bradley E. Smith65July 2013
Randy Maultsby48November 2021
Class II
Michael G. Barnes55August 2010
Dominique Mielle (Chair of the CNG Committee)53January 2020
Paul M. Friedman has been a member of our Board of Directors in accordance withsince August 2016 and was appointed Chairman of the Audit Committee Charter.in August 2020. He was the Chairman of the CNG Committee from 2016 until August 2020. From November 2009 to March 2015, Mr. Friedman served as the Senior Managing Director and Chief Operating Officer of Guggenheim Securities LLC. From June 2008 to October 2009, Mr. Friedman served as a Managing Director of Mariner. Mr. Friedman spent 27 years at Bear Stearns & Co. Inc. (“Bear Stearns”) from 1981 to 2008, most recently holding the position of Chief Operating Officer of its Fixed Income Division. Mr. Friedman serves as the Lead Director and the chairman of the Compliance Committee of Oppenheimer Holdings Inc. and on the board of directors of Great Ajax Corp., where he is a member of both the audit and compensation committees. He also joined the board of Intelligo in 2020. Mr. Friedman has a M.S. in Finance and Accounting from New York University, Stern School of Business, and a B.A. in Economics from Colgate University.

Mr. Friedman was selected and qualified to serve as a member of our Board of Directors because of his diverse
18

and extensive business and financial experience as well as his experience on the boards of other public companies.

Bradley E. Smith has been a member of our Board of Directors since July 2013. Mr. Smith was a member of the board of directors of Tiptree Financial Partners, L.P. (“TFP”) from June 2007 to July 2013. He is the founder of Kahala Capital Advisors LLC, a private investment firm, and of Kahala Aviation Ltd., a commercial aircraft leasing company. Prior to Kahala Capital, Mr. Smith worked for almost 20 years in banking in New York and Asia. He was employed from 1995 until 2000 at Bear Stearns, where he started its credit derivatives businesses in New York; and later as a Senior Managing Director, based in Tokyo, managing the firm’s fixed income and derivative businesses. Before Bear Stearns, Mr. Smith spent 10 years with Bankers Trust Company (“Bankers Trust”) as a syndicate manager in its loan syndications group, where he was responsible for the syndication of some of the largest leveraged loan financings ever completed. Afterwards, he transferred to Tokyo and later to Hong Kong, where he was involved in Bankers Trust’s credit trading businesses in Asia. In his last position at Bankers Trust, Mr. Smith was one of the founders of that bank’s credit derivatives business. Mr. Smith holds a B.A. from St. Joseph’s University and an M.B.A. from the American Graduate School of International Management.
Mr. Smith was selected and qualified to serve as a member of our Board of Directors because of his knowledge as a private investor and entrepreneur, experience involving large complex financial transactions and his extensive international relationships.
Randy S. Maultsby was appointed a member of our Board of Directors on November 2, 2021 and was also appointed as our President on July 14, 2021. Previously, he served as the Company’s Managing Director. Mr. Maultsby focuses on corporate strategy and development, overseeing the Company’s acquisition, disposition and capital markets activities. Prior to joining Tiptree Inc. in 2010, Mr. Maultsby was a senior vice president in the investment banking division of Fox-Pitt, Kelton. During his investment banking career, he focused on providing strategic advice to a broad array of banks, finance, asset management and brokerage clients. Prior to joining Fox-Pitt, Kelton, Mr. Maultsby was an Associate in the M&A Group at JP Morgan and an analyst in the Financial Institutions Group at Citigroup. He is a member of the Board of Directors of Invesque Inc., where he also serves on the audit committee. Mr. Maultsby received his BA in Political Science, with Honors, from Hampton University.
Mr. Maultsby was selected and qualified to serve as a member of our Board of Directors because of his extensive senior level experience in the capital market industry and his extensive knowledge of our business and industries.
Michael G. Barnes has been a member of our Board of Directors since August 2010, and he currently serves as the Chairman of our Board of Directors.He is also the Company’s Executive Chairman and a member of the management executive committee. In 2007 Mr. Barnes founded Tiptree Financial Partners, L.P. (“TFP”), Tiptree’s predecessor, and served as Chief Executive Officer until 2012 and Chairman until its merger with Tiptree in 2018. In addition, Mr. Barnes is a founding partner and principal of Corvid Peak Holdings, L.P., formerly known as Tricadia Holdings, L.P., and its affiliated companies. Prior to the formation of Corvid Peak in 2003, Mr. Barnes spent two years as Head of Structured Credit Arbitrage within UBS Principal Finance LLC, a wholly owned subsidiary of UBS Warburg that conducted proprietary trading on behalf of the firm. Mr. Barnes joined UBS in 2000 as part of the merger between UBS and PaineWebber Inc. Prior to joining UBS, Mr. Barnes was a Managing Director and Global Head of the Structured Credit Products Group of PaineWebber. Prior to joining PaineWebber in 1999, he spent 12 years at Bear Stearns, the last five of which he was head of their Structured Transactions Group. Mr. Barnes was the Chairman of the Board of Philadelphia Financial Group, Inc., a private placement life insurance, annuity and administration company, from June 2010 until June 2015 and Care Investment Trust Inc., a senior living real estate company, from August 2010 until February 2018. Mr. Barnes received his A.B. from Columbia College.
Mr. Barnes was selected and qualified to serve as a member of our Board of Directors because of his extensive senior level experience in the investment management industry and his extensive knowledge of our business and industries.

Dominique Mielle has been a member of our Board of Directors since January 2020 and was appointed as the Chairperson of the CNG Committee in August 2020. Ms. Mielle was a partner and senior portfolio manager at Canyon Partners, where she worked from 1998 to 2017, focusing on the transportation, technology, retail and
19


consumer products sectors, corporate and municipal bond securitizations and leading Canyon’s collateralized loan obligations business. She was named one of the “Top 50 Women in Hedge Funds” by Ernst & Young in 2017. Prior to joining Canyon in 1998, Ms. Mielle worked at Libra Investments, Lehman Brothers and Credit Lyonnais. Ms. Mielle was a director of PG&E Corporation and Pacific Gas and Electric Company from April 2019 until June 2020, where she was the chair of the audit committee. She was a director of Anworth Mortgage Asset Corporation, a mortgage REIT investment firm, where she was the chair of the compensation committee and served on the audit and compensation, nominating and corporate governance committees from 2018 until its merger with Ready Capital Corp. in March 2021. In connection with the merger, Ms. Mielle became a director of Ready Capital Corp. Ms. Mielle also has been a director of Studio City International since 2018, where she is the chair of the nominating and corporate governance committee and serves on the compensation and audit and risk committees. She has also been a director of Digicel Group since July 2020 and became a director of Osiris Acquisition Corp. in May 2021 where she is the chair of their audit committee. Ms. Mielle graduated with an M.B.A. (Finance) from Stanford University and a Master in Management degree from Ecole des Hautes Etudes Commerciales in France (HEC Paris).
Ms. Mielle was selected and qualified to serve as a member of our Board of Directors because of her extensive financial services industry experience on Wall Street, investing in fixed income and leading capital structure optimizations and restructurings.
BOARD DIVERSITY MATRIX
The members of our board of directors have provided the diversity information below as of March 31, 2022. Each of the categories listed in the table below has the primarymeaning as it is used in Nasdaq Rule 5605(f).
Total Number of Directors7
FemaleMaleNon-BinaryDid Not Disclose Gender
Part I: Gender Identity
Directors23—2
Part II: Demographic Background
African American or Black—1——
Alaskan Native or Native American————
Asian————
Hispanic or Latinx————
Native Hawaiian or Pacific Islander————
White22——
Two or More Races or Ethnicities————
LGBTQ+—
Did Not Disclose Demographic Background2

EXECUTIVE OFFICERS
Set forth below is the background information regarding each of our executive officers as of March 31, 2022, other than Messrs. Barnes, Ilany and Maultsby. The biographies of Messrs. Barnes and Maultsby are listed above, under “Continuing Directors”, and Mr. Ilany’s biography is listed below under “Information Regarding the Nominees for Election”..
Sandra Bell, age 64, has been our Chief Financial Officer since July 2015. Ms. Bell brings over 35 years of business experience in the financial services and energy industries, both as a public company Chief Financial Officer and as an investment banker. Prior to joining the company, Ms. Bell served as Chief Financial Officer of Prospect Mortgage, LLC (“Prospect”), a private equity owned mortgage originator and servicer, overseeing all financial
20


activities, including strategic planning, treasury, financial reporting, bank and rating agency relationships and investor relations. Prior to joining Prospect, from 2008 to 2011, Ms. Bell served as Chief Financial Officer of PHH Corporation (“PHH”), a publicly traded, multi-divisional financial services company engaged in the private label mortgage services and fleet management businesses. Prior to PHH, Ms. Bell served as Executive Vice President and Chief Financial Officer of the Federal Home Loan Bank of Cincinnati. Prior to assuming her position at the Federal Home Loan Bank, Ms. Bell had been a Managing Director at Deutsche Bank Securities, where she had been employed for 13 years. Ms. Bell joined the Board of Directors of Chimera Investment Corporation in December 2021 and serves on their Audit Committee and their Risk Committee. She received a B.A. degree in Economics from The Ohio State University and a M.B.A. from Harvard Business School.
Neil C. Rifkind, age 55, has been our Vice President, General Counsel and Secretary since July 2013. From 2011 until July 2013, Mr. Rifkind was Special Counsel at the law firm of Schulte Roth & Zabel LLP, specializing in mergers and acquisitions and securities law. From 2006 through 2010, he was an associate at Schulte Roth & Zabel LLP. From 1998 until 2006, Mr. Rifkind was an associate at the law firm of Fried, Frank, Harris, Shriver & Jacobson LLP. Mr. Rifkind received a J.D. from Boston University School of Law, an M.A. in Philosophy from the University of Toronto and an A.B. in Philosophy from the University of Chicago.


21

PROPOSALS TO BE VOTED ON
PROPOSAL 1: ELECTION OF DIRECTORS
Our Board of Directors is classified into three classes: Class I, consisting of Paul M. Friedman, Bradley E. Smith and Randy Maultsby, to hold office for a term expiring at the 2023 annual meeting; Class II, consisting of Michael G. Barnes and Dominique Mielle, to hold office for a term expiring at the 2024 annual meeting; and Class III, consisting of Jonathan Ilany and Lesley Goldwasser, to hold office for a term expiring at this Annual Meeting of stockholders.
Our Fourth Amended and Restated Bylaws (“Bylaws”) provide that a majority of the entire Board of Directors may establish, increase or decrease the number of directors, provided that the number of directors shall never be less than one (1), which is the minimum number required by the Maryland General Corporation Law, nor more than fifteen (15).
Information Regarding the Nominees for Election
The following table and biographical descriptions set forth certain information, as of March 31, 2022, with respect to each nominee for election as director at the Annual Meeting. Mr. Ilany and Ms. Goldwasser each currently serve as a director.
All nominees for director have consented to be named and have agreed to serve as directors if elected. We have no reason to believe that any of the nominees will be unable to accept election as a director. However, in the event that one or more nominees are unable or unwilling to accept election or are unable to serve for any reason, the persons named as proxies or their substitutes will have authority, according to their judgment, to vote or refrain from voting for such substitute as may be designated by the Board of Directors.
Nominees for Election as Class III DirectorsAgeDirector Since
Lesley Goldwasser (Lead Independent Director)60January 2015
Jonathan Ilany68August 2010

Lesley Goldwasser has been a member of our Board of Directors since January 2015. Ms. Goldwasser has been a Managing Partner of GreensLedge Capital Markets LLC (“GreensLedge”) since September 2013. Prior to joining GreensLedge, Ms. Goldwasser was associated with Credit Suisse Group AG (“Credit Suisse”) as a Managing Director from September 2010 to November 2013, where she had global responsibility for the preparationHedge Fund Strategic Services unit. Before Credit Suisse, Ms. Goldwasser spent 12 years at Bear Stearns where she was co-head of Global Debt and presentationEquity Capital Markets units and integrityhad global responsibility for structured products. Prior to her tenure at Bear Stearns, Ms. Goldwasser spent 12 years at Credit Suisse in a variety of management positions, including responsibility for both the Asset Backed and Non-Agency Mortgage Trading Desks. She is on the Board of Directors of Liquid Telecom and FinTech Acquisition Corp. V. and joined the board of FTAC Parnassus Acquisition Corp. in March 2021. Ms. Goldwasser is a graduate of the University of Cape Town, South Africa.

Ms. Goldwasser was selected and qualified to serve as a member of our Board of Directors because of her diverse and extensive business and financial statementsexperience across a variety of investment banking disciplines.

Jonathan Ilany is our Chief Executive Officer and has representeda member of our Executive Committee. He is also a member of our Board of Directors. From February 2015 to November 2015, Mr. Ilany was our Co-Chief Executive Officer. From October 2014 until February 2015, he was our Executive Vice President, Head of Mortgage Finance and Asset Management. Mr. Ilany served as a director of Rescap, a subsidiary of Ally Bank from November 2011 until December 2013. From 2005 until 2018, Mr. Ilany was a private investor and passive partner at Mariner Investment Group (“Mariner”). Mr. Ilany was a partner at Mariner from 2000 until 2005, responsible for hiring and setting up new trading groups, overseeing risk management and serving as a senior member of the AuditInvestment Committee that such financial statements were prepared in accordance with generally accepted accounting principles. In fulfilling its oversight responsibilities,and Management Committee. From 1996 until 2000, Mr. Ilany was a private investor. From 1982 until 1995, Mr. Ilany held various senior management roles at Bear Stearns, including as a Senior Managing Director and
22

a member of the Audit Committee reviewed the audited financial statementsboard of directors. From 1980 until 1982, Mr. Ilany worked at Merrill Lynch. From 1971 until 1975, Mr. Ilany served in the Annual Report on Form 10-K for the year ended December 31, 2015 with management, including a discussionarmored corps of the quality, not justIsraeli Defense Forces, and he was honorably discharged holding the acceptability,rank of First Lieutenant. Mr. Ilany received his B.A. and M.B.A. from the accounting principles, the reasonablenessUniversity of significant judgmentsSan Francisco.

Mr. Ilany was selected and the clarityqualified to serve as a member of disclosuresour Board of Directors because of his extensive risk management and senior managerial experience in the financial statements.services industry, his board experience, his experience with investing in real estate and real estate-related assets and his extensive knowledge of our business and industries.
Vote Required and the Recommendation of the Board
The vote of a plurality of all of the votes cast at the Annual Meeting, assuming a quorum is present, is necessary for the election of each Class III director. Therefore, the two nominees for director receiving the most “FOR” votes will be elected. For purposes of the election of directors, withheld votes and broker non-votes, if any, will not be counted as votes cast and will have no effect on the result of the vote, although they will be considered present for the purpose of determining the presence of a quorum.

THE BOARD OF DIRECTORS UNANIMOUSLY RECOMMENDS A VOTE
“FOR”
ALL DIRECTOR NOMINEES.

23



PROPOSAL 2: APPROVAL OF AN AMENDMENT TO THE COMPANY’S 2017 OMNIBUS INCENTIVE PLAN

We are asking stockholders to approve the Amendment (the “Amendment”) to the Tiptree Inc. 2017 Omnibus Incentive Plan (as amended from time to time, the “2017 Plan”), which amends the 2017 Plan to increase the number of shares available for issuance thereunder by 4,000,000 shares. As of March 31, 2022, 2,134,097 shares remained available for future grants under the 2017 Plan, which is our only incentive award plan with shares available for issuance. Our AuditBoard of Directors and CNG Committee reviewedbelieve that this share increase is necessary to ensure that the Company has a sufficient reserve of shares available to attract and retain the services of key individuals essential to the Company’s long-term growth and success. No other material changes to the 2017 Plan are proposed. A copy of the Amendment is attached to this Proxy Statement as Annex A, and the discussion in this proposal is qualified in its entirety by the full text of the Amendment.

The Amendment was adopted by our Board of Directors, upon recommendation from our CNG Committee on April 5, 2022, subject to stockholder approval. Currently, the 2017 Plan provides that the maximum number of shares available for issuance pursuant to awards issued thereunder is 6,100,000 shares of our common stock. If the stockholders do not approve the Amendment, the Amendment will not become effective, the 2017 Plan will continue in effect (without giving effect to the Amendment), and we will be subject to the current share limit set forth in the 2017 Plan. Following stockholder approval of the Amendment to increase the share pool available under the 2017 Plan, our Executive Chairman, Chief Executive Officer and President may elect to exchange PRSUs for performance-based restricted stock having the same economic and vesting terms but with current voting rights. Because certain of our directors and executive officers may be eligible to receive awards under the 2017 Plan, such directors and executive officers may be considered to have an interest in this proposal. The material features of the 2017 Plan as amended by the Amendment are described under “Summary of the 2017 Plan as Amended” below.

Rationale for the Amendment
During the beginning of 2022, in its determination to recommend that the Board adopt the Amendment, the CNG Committee considered advice and input presented by management with the assistance of Compensation Advisory Partners LLC (“CAP”) as its independent compensation consultant. Our Board of Directors believes that equity awards are a critical part of our compensation program and allow us to attract and retain key talent, incentivize sustainable growth and long-term value creation, and align the interests of our employees with those of our stockholders. Our Board of Directors approved the Amendment because it believes, based in part on input from CAP, that we do not currently have a sufficient number of shares available under the 2017 Plan to continue to grant equity awards in line with our independent auditors, who are responsible for auditing our financial statements and for expressing an opinion onhistorical practices. In setting the conformitysize of those audited financial statements with accounting principles generally acceptedthe share pool under the Amendment, the Board of Directors considered the historical amounts of equity awards granted by the Company in the United States, their judgment aslast three years. In fiscal 2019, 2020 and 2021, we made equity awards under the 2017 Plan totaling 708,351 shares, 977,446 shares, and 1,443,603 shares, respectively. In 2021, 80% or 1,166,307 shares out of the 1,443,603 shares issued from the 2017 Plan, were to satisfy exchange obligations of Tiptree shares for vested subsidiary awards to key personnel at our mortgage origination subsidiary, which had a record year of performance. Such exchange obligations are not recurring obligations but rather one-time in nature.

As of March 31, 2022, a total of 2,134,097 shares remain available for issuance under the 2017 Plan, which is our only incentive award plan with shares available for issuance. Such remaining shares were intended to be used to satisfy one-time subsidiary awards that are exchangeable for shares of the Company’s common stock. However, a significant portion of such subsidiary awards will no longer be exchangeable for the Company’s common stock upon closing of the $200 million strategic investment in Fortegra by Warburg Pincus pursuant to the quality, not justSecurities Purchase Agreement between and among Tiptree, Fortegra and WP Falcon Aggregator, L.P. dated October 11, 2021. As such, the acceptability,Company expects that the addition of 4,000,000 shares to the 2017 Plan will provide the Company with enough shares to satisfy the remaining subsidiary awards outstanding, satisfy issuance of shares for any vested PRSUs and have enough shares remaining for future equity grants to our other employees.

24


As of March 31, 2022, the last reported sale price of our accounting principlescommon stock on Nasdaq was $12.85 per share.

In 2021, a total of 3,500,000 PRSUs were granted to our Executive Chairman, Chief Executive Officer and such other matters asPresident. The PRSUs vest into shares of common stock upon Tiptree’s 30 trading day average stock price achieving each of five stock price milestones ranging from $15 to $60, reduced by the aggregate amount of dividends paid. The PRSUs are requiredintended to cover three years of equity compensation for the Executive Chairman, Chief Executive Officer and President, and the CNG Committee does not intend to grant new equity awards to them over the next three years. As discussed above in Summary—Compensation Highlights, the PRSU awards are intended to pay out only upon the delivery of extraordinary performance (i.e., annualized total shareholder returns of ~20%). If the Company does not meet the target stock price goals over the 10-year performance period then these awards will not result in any incremental dilution. Of the 3.5 million PRSUs granted, 2.1 million, or 60% of the total, are contingent on Tiptree achieving the final two stock price hurdles of $45 and $60, which represent significant appreciation from the grant date stock price of $9.70. While the PRSUs were granted on August 4, 2021 when Tiptree’s closing stock price was $9.70, given their significant price target hurdles, the grant date fair value for each PRSU granted was $2.79 each based on a Black-Scholes-Merton option pricing formula. Following stockholder approval of the Amendment to increase the share pool available under the 2017 Plan, our Executive Chairman, Chief Executive Officer and President may elect to exchange PRSUs for performance-based restricted stock having the same economic and vesting terms but with current voting rights.

As of March 31, 2022, the Company did not have sufficient shares available in the 2017 Plan to settle for shares all of the PRSUs awarded. A significant portion of the 4,000,000 proposed additional shares is expected to be discussed withused to satisfy issuance of shares for any of the Audit3,266,667 unvested PRSUs. If the Amendment is not approved, then the Company may need to settle in cash those PRSUs that vest. In November 2021, the first tranche of the PRSUs ($15 share price target) vested, resulting in a net issuance of 215,583 shares of Tiptree common stock under the 2017 Plan.

The below table illustrates the aggregate number of PRSUs that will vest upon the achievement of each Tiptree share price target. Such price targets will be adjusted down for cumulative dividends paid by the Company since grant (e.g., the next share price target is $19.88 as adjusted for cumulative dividends paid to date). As the table shows, the PRSUs only vest upon extraordinary total shareholder returns (i.e., ~ 20% annualized total shareholder return over the performance period) yielding substantial increases in Tiptree’s market value at achievement of each price target. In other words, Tiptree’s market value would need to increase at a minimum of $1.7 billion in order for all the PRSUs to vest.
Price TargetShares EarnedDetermination Period
Minimum Annualized Return through End of Determination Period(1)
Incremental Increase of Tiptree’s Market Value at Price Target(2)
Shares Earned as Percentage of Shares Outstanding(3)
$15233,333Before August 4, 202324.35%$182,243,6910.67%
$20466,667Before August 4, 202519.83%$183,722,8251.34%
$30700,000Before August 4, 202720.70%$374,445,6401.98%
$45933,333Before August 4, 202921.14%$582,668,4452.59%
$601,166,667Before August 4, 203119.99%$624,668,4753.16%

(1) Based on grant date closing stock price of $9.70.
(2) Based on 34,877,897 shares outstanding as of March 31, 2022, the increase in Tiptree’s market value at achieving each price target as compared to a share price of $9.70 at grant of the PRSUs, assuming Tiptree’s shares outstanding increases solely to include the incremental common stock issued for vested PRSUs at achievement of each price target.
(3) At the $15 price target, this is based on 34,877,897 shares outstanding as of March 31, 2022. At each subsequent price target, the shares outstanding is increased solely to include the incremental common stock issued for vested PRSUs at achievement of each price target.

Our three-year average burn rate — the number of shares granted, PRSUs earned and subsidiary awards exchanged in each fiscal year divided by the weighted shares of our common stock outstanding at fiscal year end —
25


is 3.10%. This burn rate is higher than our historical average given that 80% of the shares granted in 2021 (1,166,307 shares out of the total 1,443,603 shares granted) were to satisfy exchange obligations of Tiptree shares for vested subsidiary awards to key personnel at our mortgage origination subsidiary, which had a record year of performance. Excluding one-time subsidiary award exchanges, our three-year average burn rate is 1.92%.
In setting the size of the share pool under the Amendment, the Board of Directors also considered the total amount of equity awards outstanding under existing grants as of March 31, 2022, as further shown in the chart below. Based on an analysis by CAP of the remaining shares available under the 2017 Plan, the number of equity awards outstanding under the 2017 Plan, our historic burn rate, current and proposed plan features and the equity plan guidelines established by proxy advisory firms, the Board of Directors approved the Amendment and the share pool authorized under it to ensure that we continue to have the ability to provide competitive levels of equity compensation.
If the Amendment is not approved by our stockholders, the 2017 Plan will continue in effect (without giving effect to the Amendment), and we will be subject to the current share limit set forth in the 2017 Plan, which would be insufficient to continue to grant equity awards at our current levels and will materially affect our ability to attract and retain key talent. We believe that the increase in shares available for issuance as proposed by the Amendment is reasonable, appropriate, and in the best interests of our stockholders.
Dilution and Overhang
The 2017 Plan is the only long-term incentive plan of the Company under which equity awards are currently granted to our employees and other service providers (including non-employee directors). As of March 31, 2022, 2,134,097 shares remain available for issuance under the 2017 Plan. If the Amendment to the 2017 Plan is approved by our stockholders, we will be able to grant future equity awards to our employees.
Number of shares of common stockOverhang percentage based on 43,228,621 shares outstanding
Unvested RSUs Outstanding501,0081.16%
Unexercised Options Outstanding1,715,6193.97%
Total Shares Subject to Outstanding Awards2,216,6275.13%
Shares Available for Issuance Under the 2017 Plan2,134,0974.94%
Total Overhang4,350,72410.06%
Additional Shares Requested4,000,0009.25%
Total Overhang and Additional Shares Requested8,350,72419.32%
The table above shows the overhang as of March 31, 2022 of the total shares issuable pursuant to outstanding awards, the number of shares available for future awards under the 2017 Plan and the proposed number of shares issuable under the Amendment. As noted above, as of March 31, 2022, 2,134,097 shares remain available for issuance under the 2017 Plan. Additionally, an aggregate of 2,220,561 shares may be issuable subject to outstanding awards. This represented approximately 10.06% of our pro-forma fully diluted common shares outstanding (our “overhang percentage”) as of March 31, 2022, based on 43,228,621 shares outstanding, consisting of 34,877,897 shares of our common stock outstanding as of March 31, 2022, 501,008 shares issuable upon vesting of RSUs, 1,715,619 shares issuable on exercise of outstanding stock options (assuming no cashless exercises), 2,134,097 shares available for issuance under the 2017 Plan and 4,000,000 additional shares requested pursuant to the Amendment. If our stockholders approve the Amendment, the 4,000,000 additional shares proposed to be reserved for issuance under the 2017 Plan would increase our overhang percentage from approximately 10.06% to approximately 19.32%.
Summary of the 2017 Plan as Amended
The following is a brief summary of the material terms of the 2017 Plan, as amended by the Amendment. This summary is qualified in its entirety by reference to the full text of the Amendment, which is attached to this Proxy
26


Statement as Annex A, and the full text of the 2017 Plan, which is incorporated by reference to Exhibit 10.1 of the Company’s Form S-8 Registration Statement filed on June 19, 2017.
Administration. The 2017 Plan is administered by the CNG Committee, which, subject to the provisions of the 2017 Plan, has the authority to, among other things:
•Select the recipients of awards;
•Determine the types of awards to be granted;
•Determine the number of shares or dollar value covered by each award;
•Determine the terms and conditions of each award;
•Determine modify or waiver the terms and conditions of any award;
•Determine the form and timing of settlement of each award;
•Interpret and administer the plan;
•Correct any defect, supply any omission or reconcile any inconsistency in the 2017 Plan or any award;
•Establish rules and regulations; and
•Make any other determination or take any other action that it deems necessary and advisable.
The functions of the CNG Committee may be performed by a subcommittee thereof or another committee designated by the Board of Directors and the CNG Committee (or such subcommittee or other committee) may delegate certain of its powers and responsibilities under Public Company Accounting Oversight Board (PCAOB) Auditing Standard No. 16, the 2017 Plan. As used in this summary, “CNG Committee” refers to the CNG Committee, any such subcommittee or other committee or any of their respective authorized delegates, as applicable. Decisions of the CNG Committee are final, conclusive and binding on all persons.
EligibilityCommunications with Audit Committees. .In addition, the Audit Committee has received from our independent auditors written disclosures regarding the auditors’ independence required by PCAOB EthicsThe 2017 Plan provides that awards may be granted to key employees, directors, consultants (whether or not natural persons) and Independence Rule 3526, Communication with Audit Committees Concerning Independence, and has discussed with the independent auditors, their independence fromother service providers of the Company and its management. In concludingsubsidiaries and to certain other individuals who are reasonably anticipated to begin providing direct services to the Company or a subsidiary within twelve (12) months after the date an award is granted. Incentive stock options (“ISOs”) may be granted only to employees of the Company or certain subsidiaries. As of March 31, 2022, we estimate that approximately 1,472 persons would be eligible to participate in the independent auditors are independent,2017 Plan.
Number of Shares Authorized.Subject to adjustment as described below, the Audit Committee considered, among other factors, whethernumber of shares of our common stock authorized for issuance in satisfaction of awards under the non-audit services provided2017 Plan, as amended by the independent auditorsAmendment is 10,100,000 shares (the “Share Pool”). Up to 1,000,000 shares from the Share Pool may be issued in 2015 were compatible with its independence.respect of stock options intended to qualify as ISOs. For purposes of the Share Pool:
Our Audit Committee discussed with our independent auditors•If any award is settled in cash or otherwise expires, becomes unexercisable, terminates or is forfeited to or repurchased by the overall scopeCompany due to failure to vest, the shares underlying such award will not reduce the Share Pool;
•Shares issued in assumption of, or in substitution or exchange for, awards previously granted by an acquired entity (“substitute awards”) will not reduce the Share Pool;
•All shares covering a SAR, any portion of which is settled in stock, will reduce the Share Pool;
•Shares delivered under the 2017 Plan that are subsequently repurchased using proceeds directly attributable to stock option exercises will not increase the Share Pool; and plans for their audit. Our Audit Committee met with our independent auditors, with
•All shares withheld in payment of the exercise or purchase price of an award or in satisfaction of tax withholding obligations will reduce the Share Pool.
Shares issued under the 2017 Plan may consist of authorized and without management present,unissued shares, treasury shares, shares held by a subsidiary, shares purchased in the open market or other shares.
Individual Limits.Subject to discussadjustment as described below, the resultsmaximum number of their examinations,shares subject to stock options and SARs that may be granted, and the overall qualitymaximum number of our financial reporting.shares subject to other stock-based awards that
In reliance on
27


may be granted, to any participant in any calendar year is, in each case, 2 million shares. The maximum amount that may be earned by any participant in any calendar year in respect of cash-based awards is $10 million.
Non-Employee Director Limits.The aggregate value of all compensation granted or paid to any non-employee director with respect to any calendar year, including awards under the reviews2017 Plan and discussions referredother compensation paid by the Company, in each case, for the director’s service to above, the Audit Committee recommended to our Board of Directors, may not exceed $750,000.
Types of Awards.The 2017 Plan provides for the grant of stock options, SARs, restricted stock, restricted stock units (“RSUs”), performance awards and other share-based awards. Dividend equivalents may also be provided in connection with awards other than the PRSUs granted in 2021, stock options or SARs under the 2017 Plan.
Awards under the 2017 Plan may be granted alone or in combination with other awards.
•Stock Options and SARs. The CNG Committee may grant stock options, including ISOs, and SARs under the 2017 Plan. A stock option is a right to purchase, upon exercise, shares during a specified period of time at a specified exercise price. A SAR entitles the recipient to receive, upon exercise, the excess of the fair market value of a share of our common stock on the date of exercise over the base value of the SAR. The per share exercise price for each stock option, and the base value for each SAR, granted under the 2017 Plan may not be less than 100% of the fair market value of a share of our common stock on the date of grant (110% in the case of certain incentive stock options). The term of each stock option and SAR granted under the 2017 Plan may be no longer than ten years from the date of grant (five years in the case of certain ISOs). Other than adjustments in connection with certain corporate transactions or changes to our corporate structure as described below, stock options and SARs granted under the 2017 Plan may not be amended to reduce the exercise price or base value of such award or be cancelled in exchange for stock options or SARs with a lower exercise price or base value, nor may any consideration be paid upon the cancellation of any stock options or SARs that have a per share exercise price or base value greater than the auditedfair market value of a share of our common stock on the date of such cancellation, in each case, without stockholder approval. No stock option or SAR granted under the 2017 Plan may provide for automatic “reload” grants of additional awards upon exercise.
•Restricted Stock. Restricted stock is stock issued subject to such restrictions as the CNG Committee may impose, including restrictions on transferability.
•Restricted Stock Units.RSUs are awards valued by reference to shares of our common stock, which may be paid in cash, shares, other property or a combination thereof, and which are subject to such restrictions as the CNG Committee may impose.
•Other Share-Based Awards. The CNG Committee may grant other awards that are valued in whole or in part by reference to, or are otherwise based on, shares of our common stock or other property under the 2017 Plan. Other share-based awards may be paid in cash, shares, other property or a combination thereof.
•Performance Awards. The CNG Committee may grant cash-denominated incentives and units valued by reference to a designated number of shares of our common stock, which will be paid upon the achievement of performance goals established by the CNG Committee.
Vesting; Minimum Vesting; Terms of Awards. The CNG Committee determines the terms and conditions of all awards granted under the 2017 Plan, including vesting conditions, and the effect of termination of employment on outstanding awards. No portion of any award granted under the 2017 Plan may be scheduled to vest or become exercisable prior to the one year anniversary of the date of grant, except that up to 5% of the shares reserved for issuance may be granted without regard to this minimum vesting and exercisability provision.
Transferability of Awards.In general, no awards or shares subject to awards may be transferred, other than by wills or laws of descent or distribution. However, the CNG Committee may permit transfers of awards other than ISOs to certain family members, trusts for the benefit of the participant or certain family members, controlled entities or as charitable donations.
28


Performance Criteria.The 2017 Plan permits the CNG Committee to grant awards subject to “performance criteria.” Performance criteria will be subject to the achievement of one or more objective performance goals or measures established by the CNG Committee.
Adjustments.In the event of any merger, reorganization, consolidation, recapitalization, extraordinary distribution, stock split, reverse stock split, spin-off or similar transaction or change in the Company’s corporate structure, the CNG Committee may make such adjustments and substitutions to the 2017 Plan and to awards under it as it deems equitable or appropriate to prevent dilution or enlargement of the rights under the 2017 Plan, including adjustments to:
•The number of shares, class and kind of securities that may be delivered under the 2017 Plan;
•The individual limitations described above; and
•The number, class, kind and exercise price of securities subject to outstanding awards.
Effect of Certain Transactions.Subject to the change in control provisions described below, and except as may be provided in an award agreement, in the event of certain covered transactions, including the consummation of a merger, consolidation, the sale of substantially all of the Company’s assets or stock, or a dissolution or liquidation of the Company, the CNG Committee may provide:
•    For the assumption, substitution or continuation of some or all awards (or any portion thereof) by the acquirer or surviving entity;
•    For a payment in respect of some or all awards (or any portion thereof) equal to the excess, if any, of the fair market value of the shares subject to the award, over the aggregate exercise or base value, if any, on such terms and conditions as the CNG Committee determines; and/or
•    For the acceleration of exercisability or delivery of shares in respect of some or all awards (or any portion thereof), in full or in part.
Except as the CNG Committee may otherwise determine, each award will automatically terminate upon the consummation of the covered transaction, other than awards that are substituted for or assumed and any cash-based awards that continue following the transaction.
Change in Control.Except as may be provided in an award agreement, in the event of a change in control (generally, the sale of all or substantially all of the Company’s assets, the acquisition of 50% of the Company’s voting stock by an unrelated person or group of persons or a merger pursuant to which any person or persons become the beneficial owner of more than 50% of the Company’s voting stock):
•    If equity-based awards are assumed, replaced or continued, if a participant’s employment is terminated without cause within 24 months following the change in control, the participant’s awards will vest in full, except that any performance awards will be considered to be earned at target and prorated based on the portion of the applicable performance period completed as of the date of termination of employment; and
•    To the extent equity-based awards are not assumed, replaced or continued, such awards will vest in full, except that any performance awards will be considered to be earned at target and prorated based on the portion of the applicable performance period completed as of the date of the change in control.
Clawback. We mitigate risk through a clawback policy contained in our Incentive Compensation Clawback Policy effective January 1, 2017. If the Company files an accounting restatement, then, with respect to any recipient of an award under the Company’s plans whose misconduct led to the restatement, the CNG Committee may, at its discretion, require any bonus (whether cash, RSUs or options) paid or granted to such recipient based on the incorrect financial statements, be includedrepaid to the Company in an amount determined by the CNG Committee. In addition, any bonus (whether cash, RSUs or options) paid or granted to the recipient will be subject to clawback to the maximum extent required to comply with the Dodd-Frank Act.
Effective Date, Amendments and Termination.Unless earlier terminated by the Board, the 2017 Plan will terminate on, and no further awards be granted after, June 6, 2027, which is the tenth anniversary of the date the 2017 Plan was originally approved by shareholders. Our Board of Directors may alter, amend, suspend or terminate
29


the 2017 Plan at any time, subject to stockholder approval to the extent required by applicable law, provided that participant consent will be required if any such amendment, suspension of termination materially impairs the participant’s rights under any outstanding award under the 2017 Plan, unless required by applicable law.

Certain Federal Income Tax Consequences
The following is a summary of certain U.S. federal income tax consequences associated with certain awards granted under the 2017 Plan. The summary does not purport to cover federal employment tax or other U.S. federal tax consequences that may be associated with the 2017 Plan, nor does it cover state, local or non-U.S. taxes. The Company’s ability to deduct compensation will be subject to applicable limits under the Internal Revenue Code (the “Code”).
Stock Options (other than ISOs). In general, a participant has no taxable income upon the grant of a stock option that is not intended to be an ISO (an “NSO”) but realizes income in connection with the exercise of the NSO in an amount equal to the excess (at the time of exercise) of the fair market value of the shares acquired upon exercise over the exercise price. A corresponding deduction is generally available to the Company. Upon a subsequent sale or exchange of the shares, any recognized gain or loss is treated as a capital gain or loss for which the Company is not entitled to a deduction.
ISOs.In general, a participant realizes no taxable income upon the grant or exercise of an ISO. However, the exercise of an ISO may result in alternative minimum tax liability to the participant. Generally, a disposition of shares purchased pursuant to an ISO within two years from the date of grant or within one year after exercise produces ordinary income to the participant (and generally a deduction to the Company) equal to the value of the shares at the time of exercise less the exercise price. Any additional gain recognized on the disposition is treated as a capital gain for which the Company is not entitled to a deduction. If the participant does not dispose of the shares until after the expiration of these one- and two-year holding periods, any gain or loss recognized upon a subsequent sale of shares purchased pursuant to an ISO is treated as a long-term capital gain or loss for which the Company is not entitled to a deduction.
SARs. The grant of a SAR does not itself result in taxable income, nor does taxable income result merely because a SAR becomes exercisable. In general, a participant who exercises a SAR for shares of stock or receives a payment in cancellation of a SAR will have ordinary income equal to the amount of any cash and the fair market value of any stock or other property received. A corresponding deduction is generally available to the Company.
Restricted Stock Awards.A participant who is awarded or purchases shares subject to a substantial risk of forfeiture generally does not have income until the risk of forfeiture lapses. When the risk of forfeiture lapses, the participant has ordinary income equal to the excess of the fair market value of the shares at that time over the purchase price, if any, and a corresponding deduction is generally available to the Company. However, a participant may make an election under Section 83(b) of the Code to be taxed on restricted stock when it is acquired rather than when the substantial risk of forfeiture lapses. A participant who makes an effective 83(b) election will realize ordinary income equal to the fair market value of the shares as of the time of acquisition less any price paid for the shares. A corresponding deduction will generally be available to the Company. If a participant makes an effective 83(b) election, no additional income results by reason of the lapsing of the restrictions.
For purposes of determining capital gain or loss on a sale of shares awarded under the 2017 Plan, the holding period in the Annual Report on Form 10-Kshares begins when the participant recognizes taxable income with respect to the transfer. The participant’s tax basis in the shares equals the amount paid for the year ended December 31, 2015 filedshares plus any income realized with respect to the transfer. However, if a participant makes an effective 83(b) election and later forfeits the shares, the tax loss realized as a result of the forfeiture is limited to the excess of what the participant paid for the shares (if anything) over the amount (if any) realized in connection with the SEC.forfeiture.
RSUs. The grant of a RSU does not itself generally result in taxable income. Instead, the participant is generally taxed upon vesting and settlement (and a corresponding deduction is generally available to the Company), unless he or she has made a proper election to defer receipt of the shares (or cash or other property, if applicable) under Section 409A of the Code. If the shares issued in settlement of a RSU are restricted for tax purposes, the participant will instead be subject to the rules described above for restricted stock.
30


Certain Change in Control Payments.Under Section 280G of the Code, the vesting or accelerated exercisability of stock options and SARs and the vesting and payments of other awards in connection with a change in control of a corporation may be required to be valued and taken into account in determining whether participants have received compensatory payments, contingent on the change in control, in excess of certain limits. If these limits are exceeded, a substantial portion of amounts payable to the participant, including income recognized by reason of the grant, vesting or exercise of awards may be subject to an additional 20% federal tax and may be non-deductible to the Company.
Plan Benefits
Certain tables in this Proxy Statement under the heading “Compensation Discussion and Analysis,” including the Summary Compensation Table, Grants of Plan-Based Awards Table and Outstanding Equity Awards at Fiscal Year-End Table set forth information with respect to prior awards granted to our individual named executive officers under the 2017 Plan. The CNG Committee has full discretion to determine the amount of the awards to be made to participants under the 2017 Plan, subject to the limits described above under “Individual Limits” and “Non-Employee Director Limits.” Therefore, it is not possible to determine the benefits or amounts that will be received by or allocated to participants under the 2017 Plan, as amended by the Amendment.
The following table sets forth the awards that were granted to our named executive officers, our executive officers as a group, our non-employee directors as a group, and our other employees (who are not executive officers) as a group under the 2017 Plan during the 2021 fiscal year.
Name and PositionSubmitted by the Audit CommitteeNumber of Stock AwardsNumber of Performance Restricted Stock Units (assuming maximum performance)
Named Executive Officers
Michael G. Barnes, Executive ChairmanJohn E. Mack (Chairman)—1,500,000
Jonathan Ilany, Chief Executive OfficerLesley Goldwasser—1,500,000
Randy Maultsby, PresidentRichard A. Price—500,000
Sandra Bell, Chief Financial OfficerBradley E. Smith——
Neil C. Rifkind, VP, General Counsel and Secretary——
All executives as a group (5 persons)——
All non-employee board members, including nominees, as a group (4 persons)56,832 —
All other employees, as a group——

Vote Required and the Recommendation of the Board
The foregoing report shallaffirmative vote of a majority of all of the votes cast at the Annual Meeting, assuming a quorum is present, is required for approval of Proposal 2. Abstentions and broker non-votes, if any, will not be deemed incorporated by reference by any general statement incorporating by reference this proxy statement into any filing undercounted as votes cast and will have no effect on the Securities Actresult of 1933, as amended (the “Securities Act”), or under the Exchange Act, except tovote, although they will still be considered present for the extent that we specifically incorporate this information by reference, and shall npurpose of determining the presence of a quorum.


THE BOARD OF DIRECTORS UNANIMOUSLY RECOMMENDS THAT THE STOCKHOLDERS VOTE
ot otherwise be deemed filed under such Securities Act and/or Exchange Act.“FOR”
THE ADOPTION OF THE AMENDMENT TO THE 2017 OMNIBUS INCENTIVE PLAN




31



PROPOSAL 2:3: RATIFICATION OF APPOINTMENT OF THE INDEPENDENT REGISTERED PUBLIC ACCOUNTING FIRM
The Audit Committee has appointed the accounting firm
We are asking our stockholders to ratify our audit committee's appointment of KPMG to serveDeloitte & Touche LLP (“Deloitte”) as our independent registered public accounting firm for the fiscal year ending December 31, 2016, subject to ratification2022. Deloitte has audited our financial statements as of this appointment by our stockholders. KPMG acted as the Company’s independent registered public accounting firmand for the fiscal years ended December 31, 20142021 and 2015.
2020. A representative of KPMGDeloitte will be present at the Annual Meeting, will be given the opportunity to make a statement if he or she so desires and will be available to respond to appropriate questions.
Audit and Non-Audit Fees
The following table presents the approximate aggregate fees billed by KPMG,Deloitte, our independent registered public accounting firm for services performed with respect to fiscal 20152021 and 2014, respectively:2020:
 2015 2014
($ in thousands)
($ in thousands)
20212020
Audit Fees(1)
 $4,530,000
 $2,086,000
Audit Fees(1)
$6,152$4,075
Audit-Related Fees(2)
 900,050
 757,500
Audit-Related Fees(2)
$455$225
Tax Fees(3)
 22,000
 10,000
Tax Fees(3)
$682$731
All Other Fees(4)
 84,200
 78,130
All Other Fees(4)
22
Total Fees $5,536,250

$2,931,630
Total Fees$7,291$5,033
 
(1)Fees related to our annual audit, review of our quarterly reports on Form 10-Q, and review of documents filed with the SEC.
(2)Fees related to regulatory and statutory filings and acquisition related audit procedures for subsidiary entities.
(3)Fees related to tax compliance services and tax preparation services.
(4)Fees for agreed upon procedures performed at subsidiary entities and other incidental expenses.
(1)Fees related to our annual audit, review of our quarterly reports on Form 10-Q, and review of documents filed with the SEC.
(2)Fees related to procedures associated with the adoption of new accounting standards, due diligence related to acquisitions, and other attest services not required by statute or regulation.
(3)Fees related to tax compliance services and tax preparation services.
(4)Fees primarily represent accounting research subscription fees.

Pre-Approval Policies and Procedures of the Audit Committee
The Audit Committee has sole authority (with the input of management) to approve in advance all engagements of our independent registered public accounting firm for audit or non-audit services. All services provided by KPMGDeloitte in 20142020 and 20152021 were pre-approved by the Audit Committee. The Audit Committee has determined that the non-audit services provided by the Company’s independent registered public accounting firms are compatible with maintaining the accounting firm’s independence.
Ratification
The Board of Directors asks stockholders to ratify the selection of KPMGDeloitte as our independent registered public accounting firm. Stockholder ratification of the appointment of KPMGDeloitte as our independent registered public accounting firm is not required by our Bylaws or other governing documents. However, the Board of Directors is submitting the appointment of KPMGDeloitte to the stockholders for ratification as a matter of good corporate governance. If the selection is not ratified, the Audit Committee will consider whether it is appropriate to select another registered public accounting firm. Even if the selection is ratified, the Audit Committee, in its discretion, may select a different registered public accounting firm at any time during the year if it determines that such a change would be in the best interests of the Company and our stockholders.
Vote Required and the Recommendation of the Board
The affirmative vote of a majority of all of the votes cast at the Annual Meeting, assuming a quorum is present, is required for approval of Proposal 2.3. For purposes of the vote on Proposal 2,3, abstentions and broker non-votes, if any, will not be counted as votes cast and will have no effect on the result of the vote, although they will be considered present for the purpose of determining the presence of a quorum. We do not expect any broker non-votes for this proposal.

32



THE BOARD OF DIRECTORS UNANIMOUSLY RECOMMENDS THAT THE STOCKHOLDERS VOTE “FOR”
“FOR”
RATIFICATION OF THE APPOINTMENT OF KPMGDELOITTE AS OUR INDEPENDENT REGISTERED PUBLIC ACCOUNTING FIRM FOR THE FISCAL YEAR ENDING DECEMBER 31, 2016.2022.
STOCK PERFORMANCE GRAPH

33
Set forth below is a line-graph presentation comparing the cumulative total return on our Class A common stock against cumulative total returns of the Russell 2000 and the S&P North American Financial Services Index
(2)
. The performance graph shows the total return on an investment of $100 for the period beginning December 31, 2010 and ending December 31, 2015 assuming reinvestment of dividends. The stockholder return shown on the graph below is not necessarily indicative of future performance, and we will not make or endorse any predictions as to future stockholder returns. The graph and related data were furnished by ICR, LLC.

COMPENSATION DISCUSSION AND ANALYSIS

(1) Tiptree Financial’s Class A common stock has traded on the NASDAQ Capital Market under the ticker symbol “TIPT” since August 9, 2013. Prior to July 1, 2013, Tiptree Financial Inc. was formerly known as Care Investment Trust Inc. (“Care”). Care’s common stock was quoted on the OTCQX market under the ticker symbol “CVTR.”

(2) We believe it is difficult to develop a peer group of companies similar to Tiptree as Tiptree owns subsidiaries engaged in a number of diverse business activities. However, management views Tiptree and its subsidiaries as primarily engaged in financial services and accordingly, management has used the Standard and Poor’s North American Financial Services Index for comparative purposes.
.
COMPENSATION DISCUSSION AND ANALYSIS

This Compensation Discussion and Analysis (“CD&A”) describes our executive compensation philosophy and programs,program, and the decisions made by our CNG Committee with respect to the same for 2015.2021. The discussion below is intended to help you understand the detailed information for our named executive officers (“NEOs”) provided in ourthe executive compensation tables that follow this discussion and putto help place the specific pay decisions made for 2015 into2021 in context within our overall compensation program. Our NEOs are Michael Barnes, our Executive Chairman, Jonathan Ilany, our Chief Executive Officer, Randy Maultsby, our President, Sandra Bell, our Chief Financial Officer, and Neil Rifkind, our General Counsel and Secretary.


Guiding Principles and Compensation Policies

Tiptree’s executive compensation program is intended to reward our leadership for performance and to align our leadership’s interests with those of our other stockholders on an annual and long-term basis.Our CNG Committee has developed the following guiding principles for our executive compensation program:

•Pay for performance, with a highsignificant percentage of compensation depending ontied to the Company’s performance, including by aligning a significant portion of the Executive Committee’s equity compensation of our NEOs tied to the Company’s achievementgoals of generating long-term performance;stockholder value;
•Align executive compensation with stockholder interests;
Provide incentives to close the gap between the Company’s book value per share and stock trading price;
•Balance rewarding short-term and long-term performance to focus on long-term value creation;
•Retain current management, encourage loyalty and effectively attract new executives over time by providing competitive levels of compensation; and
•Make our executive compensation practices transparent.

Consistent with the foregoing, our executive compensation program generally has three primary elements: salary, performance-based annual cash incentive awards and annual long-term equity incentive awards.As described further in the table below, each element of our compensation program is tailored to incentivize performance in a specific area that we believe will promote sustained economic value over time.In addition, on a case by case basis, the Company has awarded initial cash or equity grants to attract talented executives.

34


ElementForm of CompensationPay for PerformancePrimary Objectives
Base Salary
Fixed
Cash
Adjustments to base salary take into account individual performanceAttract and retain talented executives while avoiding a high fixed cost structure
Annual Cash Incentive Award
Awards
Variable

Cash
Awards based on an earnings metric of the Company, as adjusted by the CNG Committee, and individual performanceMotivate near-term productivity and profitabilityReward the achievement of key short-term metrics
Annual Long-Term Equity Incentive AwardAwards
Variable
Awards

Performance restricted stock units (“PRSUs”) vest based on an earnings metric of the Company as adjusted by the CNG Committeeachieving share price targets
Value achieved depends on increasing stock price and individual performancegenerating long-term stockholder valueAlign executive interests with long-term stockholder value
Fully vested stockPotential value gain through stock appreciation
Restricted stock units (“RSUs”) subject to time-based vestingVestingTime-based vesting encourages retention; potential increased value gainachieved through stock appreciation
Time- and performance-based optionsVesting encourages retention; potential value gain is dependent on sustained stock trading price increase

Our CNG Committee is responsible for our executive compensation program design and administration, including evaluation of management performance and a regular review of our compensation programs and awards. Tiptree is managed by a management Executive Committee consisting of Michael G. Barnes, our Executive Chairman and Jonathan Ilany. In 2015, the Executive Committee also included Mr. Kauffman until his resignation in November 2015.Ilany, our CEO. The Executive Committee is responsible for strategic planning, capital allocation among Tiptree’s business sectors,businesses, overseeing M&A activity and risk management. Our Executive Committee provides the CNG Committee with preliminary recommendations for the discretionary elements of the compensation of the remaining NEOs other than those on the Executive Committee, to the

extent there is discretion in making compensation decisions.Committee. However, the CNG Committee approves the compensation for all NEOs, including the Executive Chairman and CEO.

Below is a summary description of the Company’s significant compensation policies.
What We Do
üPay for performanceüUse an independent compensation consultant
üGrant equity-based awards as a significant portion of our NEOs annual variable compensationüProhibit NEOs from shorting, pledging or hedging Tiptree stock (see “Corporate Governance Matters - Prohibition of Hedging and Pledging Transactions”)
üMitigate risk through a clawback policyüCNG Committee reserves right to exercise negative discretion
ü
Individual grant limits under our 2017 Omnibus Incentive Plan (discussed above)
What We Don’t Do
üNo perquisites to NEOs other than reimbursement of medical and transportation costsüNo term employment, golden parachute or severance agreements with our NEOs (other than the CFO)
üNo Section 280G or 409A tax gross-upsüLimited guaranteed bonus arrangements with our NEOs (CFO and PAO)home IT network
ü
No defined benefit pensions or supplemental retirement programs

üNo repricing of underwater stock options
üNo recycling of shares used to pay the taxes on vested RSUs
üUnder the 2013 Omnibus Plan, no individual grant may exceed $5 million in cashNo Section 280G or 500,000 shares409A tax gross-upsüNo guaranteed bonus arrangements with our NEOs
üNo defined benefit pensions or supplemental retirement programsüNo repricing of Class A commonunderwater stock or options in any year

35


We mitigate risk, in part, through a clawback policy contained in our 2013 Omnibus Plan.Incentive Compensation Clawback Policy. If the Company files an accounting restatement, duethen, with respect to material noncompliance with financial reporting requirementsany recipient of an award under securities laws orthe Company’s plans whose misconduct then any executive who knowingly or recklessly engaged in misconduct or recklessly failed to prevent or report the misconduct, shall repayled to the Companyrestatement, the CNG Committee may, at its discretion, require any bonus (whether in the form of cash, PRSUs, RSUs or options) paid or granted to the executivesuch recipient based on the incorrect financial statements, be repaid to the Company in an amount determined by the CNG Committee. In addition, any bonus (whether in the form of cash, RSUPRSUs, RSUs or options) paid or granted to the executiverecipient will be subject to clawback to the maximum extent required to comply with the Dodd-Frank Act.

NamedExecutiveOfficers

Our NEOs are the current and former executive officers whose compensation is discussed in this CD&A and whose compensation is shown in the compensation tables below.that follow this CD&A in this proxy statement. For 2015,2021, our NEOs are:are listed in the table below, which shows the base salary and incentive compensation awarded to our NEOs for their performance in 2021 in the manner that it was considered by the CNG Committee. When we refer to total compensation figures of our NEOs as they relate to 2021 in this CD&A we are referring to annual base salary paid in 2021, and cash bonuses for 2021 performance but paid in early 2022. 
Current NEOs
Michael G. BarnesExecutive Chairman
Jonathan IlanyChief Executive Officer
Sandra BellChief Financial Officer
Julia WyattChief Operating Officer
Patrick HuvaneChief Accounting Officer
Neil C. RifkindVice President, General Counsel and Secretary
Former NEOs
Geoffrey N. KauffmanFormer Co-Chief Executive Officer
Richard ClaidenFormer Chief Financial Officer

For 2015, Michael G. Barnespurposes of determining annual equity grants to our NEOs, our CNG Committee starts with a dollar amount (the “Par Value”) and Julia Wyatt were employeesdetermines the number of Tricadiashares or options based on the volume weighted average price (the “VWAP”) of the Company's common stock for the 10 trading days prior to the grant date. The amounts presented below with respect to the stock awards and Patrick Huvane was an employeeoption awards are the Par Value of Mariner. Accordingly,such grants. These amounts differ from the amounts for the same columns included in the Summary Compensation Table because they are valued using a different valuation method and because SEC rules require us to include the grant date fair value of equity awards based on the date of actual grant rather than the performance year in which they were earned. For example, the awards shown in the Summary Compensation Table for 2020 and 2019 were granted in each of those years but were based on 2019 and 2018 performance, respectively. There were no equity grants to our NEOs for the 2020 performance year.

On August 4, 2021, the Company granted Messrs. Barnes, Ilany and Maultsby an aggregate of 3,500,000 PRSUs, which are intended to cover three years of long-term incentive awards. Messrs. Barnes, Ilany and Maultsby will not directly compensated by Tiptree. This proxy statement describesreceive another award under the long-term incentive program until 2024. For purposes of the Summary Compensation Table, such PRSUs were valued using the grant date fair value, as estimated on the date of grant using a Black-Scholes-Merton option pricing formula embedded within a Monte Carlo model used to simulate the future stock prices of Tiptree, which assumes that the market requirement is achieved. For more detail, including the underlying valuation assumptions for PRSUs and stock option awards, please see Note 19, Stock Based Compensation, to our consolidated financial statements in our 2021 Annual Report on Form 10-K.

36
payments, including incentive compensation, by Tiptree

EXECUTIVE COMPENSATION
(CNG Perspective; Not a Substitute for the Summary Compensation Table)
Name and TitlePerformance YearSalary
($)		Non-Equity Incentive Plan Compensation ($)
Stock
Awards(1)
($)
Option Awards(1) ($)
Other Compensation(2)
Total
($)
Michael G. Barnes
Executive Chairman
2021$600,000$4,057,703$1,512,000—$27,583$6,197,286
2020$600,000$300,000——$25,342$925,342
2019$300,000$1,120,499$611,181$305,591$41,285$2,378,556
Jonathan Ilany
Chief Executive Officer
2021$800,000$4,057,703$1,512,000—$118,813$6,488,516
2020$800,000$300,000——$87,466$1,187,466
2019$600,000$1,680,748$916,772$458,386$81,598$3,737,504
Randy Maultsby(3)
President
2021$350,000$1,250,000$503,995—$7,644$2,111,639
Sandra Bell(4)
Chief Financial Officer
2021$450,000$680,000$340,000—$7,644$1,477,644
2020$450,000$550,000——$7,644$1,007,644
2019$400,000$460,000$115,000—$7,800$982,800
Neil C. Rifkind(5)
VP, General Counsel and Secretary
2021$450,000$680,000$340,000—$7,644$1,477,644
2020$450,000$550,000——$7,644$1,007,644
2019$375,000$460,000$115,000—$7,800$957,800
(1)For Messrs. Barnes, Ilany and Maultsby in performance year 2021, this represents 100,000, 100,000 and 33,333 shares, respectively, issued on November 22, 2021 pursuant to Tricadiavested PRSUs (the $15 target), with a closing stock price of $15.12. For all other performance years for Messrs. Barnes, Ilany and Maultsby and for all other NEOs, this represents the Par Value of equity grants (RSUs and options).
(2)For Ms. Bell and Mr. Rifkind for 2021, 2020 and 2019, and for Mr. Barnes’ and Ms. Wyatt’s servicesMaultsby for 2021, this represents premiums paid by the Company to our group health insurance provider under a Transition Services Agreementmedical expenses reimbursement plan (the “TSA”“MERP”). Mr. Barnes’s $27,583 of other compensation in 2021 consists of $7,644 attributable to the MERP, $10,169 attributable to travel reimbursements and payments, including incentive$9,770 of reimbursement for taxes associated with such travel reimbursements. Mr. Barnes’s $25,342 of other compensation by Tiptreein 2020 consists of $7,644 attributable to an affiliatethe MERP, $9,173 attributable to travel reimbursements and $8,525 of Marinerreimbursement for taxes associated with such travel reimbursements. Mr. Huvane’s services under an Administrative Services Agreement (the “ASA”). See “Certain RelationshipsBarnes’s $41,285 of other compensation in 2019 consists of $7,800 attributable to the MERP, $19,294 attributable to travel reimbursements and Related Transactions - Transactions$14,191 of reimbursement for taxes associated with Related Persons”.such travel reimbursements. Mr. Ilany’s $118,813 of other compensation in 2021 consists of $7,644 attributable to the MERP, $41,197 attributable to travel reimbursements, $15,499 that the Company paid in connection with maintaining the IT infrastructure in Mr. Ilany’s home office and $54,473 of reimbursements for taxes associated with such travel and IT reimbursements. Mr. Ilany’s $87,446 of other compensation in 2020 consists of $7,664 attributable to the MERP, $23,535 attributable to travel reimbursements, $17,837 that the Company paid in connection with maintaining the IT infrastructure in Mr. Ilany’s home office and $38,450 of reimbursements for taxes associated with such travel and IT reimbursements. Mr. Ilany’s $81,598 of other compensation in 2019 consists of $7,800 attributable to the MERP, $15,832 attributable to travel reimbursements, $15,270 that the Company paid in connection with maintaining the IT infrastructure in Mr. Ilany’s home office and $42,696 of reimbursements for taxes associated with such travel and IT reimbursements.

During 2015, (3)Mr. Kauffman,Maultsby was appointed our former Co-Chief Executive Officer, andPresident on July 14, 2021. Mr. Claiden, our former Chief Financial Officer, were each an NEOMaultsby’s stock award amount for performance year 2021 represent the grant date fair value of the Company. As previously disclosed, Mr. Kauffman resigned his employment withPRSUs granted on August 4, 2021.
(4)Ms. Bell’s stock award amounts for performance years 2021 and 2019 represent the Company on November 10, 2015 and Mr. Claiden resigned as Chief Financial OfficerPar Value of the CompanyRSU issuances on February 24, 2015, but continued17, 2022 and February 20, 2020, respectively. For the RSU issuance on February 17, 2022, Ms. Bell received matching RSUs that cliff vest after three years and deliver two shares of Tiptree stock for each RSU; as a part time employee in a consulting senior advisor rolesuch, the Par Value of the RSU issuance for 2021 was doubled accordingly.
(5)Mr. Rifkind’s stock award amounts for performance years 2021 and 2019 represent the remainderPar Value of 2015. Separation payments tothe RSU issuances on February 17, 2022 and February 20, 2020, respectively. For the RSU issuance on February 17, 2022, Mr. Kauffman are described under “- Separation Payments to Mr. Kauffman” below. Mr. Claiden did not receive any separation payments.Rifkind received matching RSUs that cliff vest after three years and deliver two shares of Tiptree stock for each RSU; as such, the Par Value of the RSU issuance for 2021 was doubled accordingly.

37



Use of Independent Compensation Consultant

The CNG Committee engaged Compensation Advisory Partners LLC (“CAP”)CAP to serve as its independent compensation consultant.consultant during 2021. CAP received instructions from, and reported to, the CNG Committee on an independent basis. CAP was also authorized by the CNG Committee to share with and request and receive from management specified information in order to prepare for CNG Committee meetings.

The CNG Committee requested CAP’s advice on a variety of matters, including the design and amount of our executive compensation program and the compensation opportunities under it, compensation strategy, market comparisons, pay and performance alignment, the advisability of peer benchmarking, executive pay trends, compensation best practices, compensation-related legislative mattersupdates and related rulemaking, and compensation plan designs and modifications. The CNG Committee met with CAP, both with and without management present, on several occasions during 2015, and also in early 20162021 with respect to compensation decisions for 20152021 performance. The CNG Committee assessed the independence of CAP pursuant to SEC and NASDAQNasdaq rules, and concluded that no conflict of interest exists that would prevent CAP from independently representing the CNG Committee. During 2015,2021, CAP did not provide any services to the Company or its affiliates other than advising the CNG Committee on executive officer compensation.

The CNG Committee does not currently use benchmarking or comparative data in making compensation decisions. In 2015,2021, however, the CNG Committee reviewed compensation practices compiled by CAP with respect to the companies that operate in the same industries as the Company to provide a reference point for pay levels and practices.practices, including practices relating to the grant of performance-vesting equity awards.

What Has Changed From 20142021 Company Performance
2021 was one of Tiptree’s best years since its founding in June 2007 and What Will Changewe made meaningful progress on our long-term strategic initiatives and delivered strong shareholder value. Tiptree’s revenues, earnings and total return to shareholders all set records. Our specialty insurer, Fortegra also produced record results, with adjusted return on equity of 22% while growing premiums and equivalents at 32%. In addition, our mortgage and shipping businesses also reported excellent results for 2016the year, benefiting from favorable market conditions. Below is a summary of our 2021 results. Additional information on our 2021 results is contained in our Annual Report on Form 10-K for the year ended December 31, 2021 filed with the SEC.

The chart below summarizes changesFull-Year 2021 Summary

($ in thousands, except per share information)FY’21FY’20
Total revenues$1,200,514 $810,301 
Net income (loss) attributable to common stockholders$38,132 $(29,158)
Diluted earnings per share$1.09 $(0.86)
Cash dividends paid per common share$0.16 $0.16 
Return on average equity11.4 %(6.4)%
Non-GAAP: (1)
Adjusted net income$63,869 $51,431 
Adjusted return on average equity16.5 %13.1 %
Adjusted EBITDA$100,776 $4,541 
Book value per share$11.22 $10.90 

•Revenues of $1.2 billion, increased 48.2%, driven by growth in insurance and shipping operations and investment gains in 2021 compared to losses in 2020. Excluding the impact from investment gains and losses, revenues increased 32.9% versus prior year.
38


•Net income of $38.1 million, increased significantly from a net loss in 2020, represented an annualized return on average equity of 11.4%.

•Adjusted net income(1) of $63.9 million, increased 24.2%, reflecting higher earnings in insurance and shipping operations. Adjusted return on average equity(1) of 16.5%, compared to 13.1% in 2020.

•Adjusted EBITDA(1) for the year ended December 31, 2021 was $100.8 million, an increase of $96.2 million from 2020, driven by realized and unrealized gains in 2021 compared to losses in 2020 (primarily Invesque), in addition to the improved operating performance noted above.

•On October 12, 2021, Tiptree announced a $200 million investment in Fortegra from Warburg Pincus, which is expected to close in Q2’22 and will result in an approximate 24% ownership of the business on an as converted basis.

Insurance (The Fortegra Group)

($ in thousands)FY’21FY’20
Gross written premiums and premium equivalents$2,194,024 $1,666,942 
Revenues$984,130 $691,061 
Income before taxes$69,857 $26,948 
Return on average equity17.1 %8.1 %
Combined ratio90.6 %91.5 %
Non-GAAP: (1)
Adjusted net income$66,782 $43,423 
Adjusted return on average equity22.2 %15.2 %

•Fortegra’s gross written premiums and premium equivalents increased 31.6% for the year driven by growth in U.S. specialty insurance lines and service contract businesses in U.S. and Europe. As a function of Fortegra’s premium growth, the combination of unearned premiums and deferred revenues on the balance sheet grew to $1,658.8 million, up $399.1 million, or 31.7%, from 2020.

•Revenues increased 42.4% for the year driven by premium growth and investment gains in 2021 compared to losses in 2020. Excluding the impact of investment gains and losses, revenues increased by 39.5% over 2020.

•For total year 2021, the combined ratio was 90.6%, compared to 91.5% in 2020. Operating and technology efficiencies contributed to an improved expense ratio, while the underwriting ratio remained stable.

•Total year 2021 income before taxes of $69.9 million compared to $26.9 million in the Company’s compensation program,prior year. Return on equity was 17.1% for 2021, as compared to 8.1% in 2020.

•Adjusted net income(1) for 2021 was $66.8 million, up 53.8% from 2014 through 2016, which are described2020, driven by revenue growth and an improved combined ratio. The adjusted return on average equity(1) was 22.2% for 2021, as compared to 15.2% in greater detail following the chart.2020.

39


 201420152016
Performance MeasureEconomic Net IncomeEconomic Net IncomeAdjusted EBITDA
Payout %50% of hypothetical management fees50% of hypothetical management fees
Executive Committee: 5.58%
Other NEOs: up to 4.5%
Incentive Compensation ElementsExecutive Committee: Cash and fully vested stockExecutive Committee: Cash, fully vested stock and time- and performance- based optionsExecutive Committee: Cash, three year cliff vested RSUs and time- and performance- based options
Other NEOs: Cash and three year annual vested RSUsOther NEOs: Cash and three year annual vested RSUsOther NEOs: Cash and three year annual vested RSUs
Tiptree Capital

During 2015, the CNG Committee reviewed the Company’s incentive compensation program
($ in thousands)FY’21FY’20
Revenues$216,384 $119,240 
Income before taxes$45,617 $(30,140)
Return on average equity22.2 %(12.7)%
Non-GAAP: (1)
Adjusted net income$28,197 $33,075 
Adjusted return on average equity16.2 %17.8 %

•Mortgage income before taxes was $28.4 million in 2021, as compared to $31.1 million in 2020, with the assistancedecrease driven by a decline in gain on sale margins, partially offset by higher servicing fees and positive fair value adjustments on the mortgage servicing portfolio. Adjusted return on average equity was 28.8% in 2021.

•Maritime transportation income before taxes was $11.6 million in 2021, as compared to $1.5 million in 2020, with the increase driven by cyclically high dry-bulk charter rates.

•Within Tiptree Capital, our investment in Invesque contributed unrealized gains of CAP and has adopted new performance criteria for purposes$3.1 million in 2021 compared to a loss of its variable compensation program for 2016 that are described$67.7 million in more detail below under “-Compensation Considerations for 2016” below.2020.

(1)For a reconciliation to GAAP financials, see “Annex B: Non-GAAP Measures”

2021 Compensation Highlights
To reflect the Executive Committee’s focus on long-term value creation, the Executive Committee and the CNG Committee agreed to use the 2016 plan’s incentive mix of cash, stock and options2021 was a milestone year for the Executive Committee’s 2015 incentive compensation.

2015 Company Performance

In 2015, Tiptree’s management completed several key initiatives, including:

Hiring a Chief Financial Officer with significant public company experience as well as additional accounting,we achieved record levels of financial reporting, tax and compliance personnel to improve our internal controls over financial reporting;
Growing revenue by 5.5x year over year, as the acquisition of Fortegra more than offset the sale of PFG;
Completing the sale of PFG for $142.8 million of proceeds to Tiptree and two future payments over the two years following closing totaling approximately $7.3 million. The sale resulted in an after tax gain of approximately $15.6 million for 2015;
Achieving profitability in our specialty finance segment, in part through the acquisition of Reliance;
Acquiring 11 seniors housing communities through Care for $84.9 million;
Making principal investments in pools of non-performing loans of approximately $39.7 million in 2015. In the first quarter of 2016, we added $8.0 million for a total investment of $47.7 million;
Investing an aggregate of $70.0 million in both Telos 2016-7, Ltd. which launched a new CLO in the second quarter of 2016 and in a Telos managed credit opportunity strategy which involves the leveraged purchase of commercial loans;
Returning $7.3 million to Class A stockholders through dividends of $3.3 million and stock repurchasesprice performance. A key performance objective for our performance-based stock options granted in past years was to achieve a 20-day volume weighted average stock price greater than the book value per share on the date of $4.0 million; and
Taking stepsgrant. This hurdle was achieved in 2021 for all stock options granted to simplify Tiptree’s corporate structure, including by creating a consolidated group among Tiptree and its subsidiaries for U.S. federal income tax purposes effective January 1, 2016.

2015 Compensation Highlights

our Executive Committee.
Compensation of the currentour NEOs is largely driven by the financial and strategic performance of the Company. Total compensation of the currentour NEOs related to fiscal 2021 was approximately $24 million compared to $4.1 million in 2015 was $6.6 million.fiscal 2020. In approving the compensation program and awards

for 2015, our2021, the CNG Committee considered a number of factors including, but not limited to the responsibilities of the executives’ positions, the executives’ experience and contributions, the competitive marketplace for executive talent and corporate performance. The 2021 increase in total NEO compensation reflects the addition of Mr. Maultsby as President in 2021 (he was not an NEO in 2020) and the significant increase in Adjusted EBITDA in fiscal 2021 versus fiscal 2020.
    
Total compensation of the current Executive Committee in 2015 was $3.4 million and total compensation of the current NEOs other than the Executive Committee in 2015 was $3.2 million. Consistent with Tiptree’s pay for performance philosophy, NEO pay mix is heavily weighted toward variable, performance-based pay, which alignsties a large portion of compensation to the achievement of our short and long term performance objectives. For 2021, each of the Executive Chairman, Chief Executive Officer and President were awarded PRSUs that vest upon Tiptree’s 30 trading day average stock price achieving each of five stock price milestones ranging from $15 to $60, reduced by the aggregate amount of dividends paid, within pre-established determination periods (subject to a catch-up vesting mechanism) occurring on the second, fourth, sixth, eighth and tenth anniversaries of the grant date. This award reflects the CNG Committee’s desire for the Executive Chairman, Chief Executive Officer and President to continue to lead Tiptree for an additional significant number of years and to create significant shareholder value over time. The PRSUs are intended to cover three years of equity compensation for the Executive Chairman, Chief Executive Officer and President, and the CNG Committee does not intend to performancegrant new equity awards to them over the next three years. To date, the first tranche of the long term objectivesPRSUs ($15
40


share price target) vested, resulting in a net issuance of Tiptree. 215,583 shares of Tiptree common stock under the 2017 Plan.

The charts below illustrate for 2015 the fixed versus variable mix of compensation for our current NEOs.NEOs in 2021. As seen in the illustration below, for 2015,2021, only 13%8.6% of compensation was fixed for the current Executive Committee while 87%91.4% was variable, of which 41%46.5% was at risk. Only 35%21.4% of the compensation of the other current NEOs at year-end was fixed while 65%78.6% was variable, of which 26%31% was at risk.

chart-1e14b4e457b34c97bd3a.jpgchart-f9f7b376b277459dabaa.jpg

Fixed compensation consists of base salary variableand other guaranteed reimbursements such as travel and information technology reimbursements and the premiums paid for executives under our medical expense reimbursement plan, or MERP. Variable compensation consists of any award based on performance and CNG Committee determination (including negative discretion) and at-risk compensation consists of any cash or stock award subject to forfeiture.

20152021 Executive Compensation Program and Decisions

Consistent with our compensation philosophy, our 2015Our 2021 executive compensation program had three primary elements: base salary, performance-based annual cash incentive awards and annual long-termlong term equity incentive awards. Although each element of compensation described below was considered separately, our CNG Committee made its determinations regarding each individual component of the compensation program in the context of the aggregate effect on total compensation for each NEO. For the Executive Committee, the Company made a partial payment ofNEOs, incentive compensation for services in December 2015 with a true upfiscal year was paid or granted, as applicable, in the first quarter of 2016. Unless otherwise noted, the partial payment and true up amounts are reported on an aggregate basis.following year.

Base Salary

The CNG Committee’s philosophypurpose of base salary is to maintain base salaries atprovide a modest levelset amount of cash compensation for each named executive officer that is not variable in nature and to use incentive compensation as the primary form of compensation.

The Executive Chairman, Chief Operating Officer and the Chief Accounting Officer were not compensated directly by Tiptree. The base salary amounts below for such individuals reflect the amounts paid by Tiptree to Tricadia and Mariner, as applicable, under the TSA and ASA, respectively, and may not reflect actual amounts received by the executives.

is generally competitive with market practices. Base salaries for NEOs and amounts paid under the TSA and ASA did not increase from 2014 to 2015 other than Mr. Huvane. The amounts payable under the TSA and ASA were fixed pursuant to the terms thereof. Base salaries for Messrs. Ilany and Rifkind and Ms. BellNEOs are based on competitive market rates for experienced executives in the financial services industry.of comparable organizations. The 2021 base salaries and amounts paid under the TSA or ASA for the services of our NEOs for 2015 were as follows:


NameBase Salary/TSA/ASA PaymentSalary
Michael Barnes$100,000 (under TSA)600,000
Jonathan Ilany$800,000
Randy Maultsby$350,000
Sandra Bell$400,000 (annualized)
Julia Wyatt
$350,000 (under TSA)(1)
Patrick Huvane$193,750 (under ASA)450,000
Neil Rifkind$375,000450,000
Total$1,768,7502,650,000
Notes
(1) Reflects the payment to Tricadia pursuant to the TSA and may not reflect the amount Ms. Wyatt actually received from Tricadia. As of
41


Effective January 1, 2016, Ms. Wyatt became an employee of a subsidiary of2022, the Company, with aCNG Committee has increased Messrs. Barnes and Ilany’s annual base salary of $300,000.to $1,000,000 and Mr. Maultsby’s annual base salary to $500,000.

Initial Cash or Equity Grants

We make initial cash or equity grants to NEOs when our CNG Committee determines that it would be to the advantage and in the best interests of Tiptree and its stockholders to make these grants as an inducement to the NEO to enter into the employ of Tiptree. For 2015, initial equity grants were only made to Ms. Bell, Tiptree’s Chief Financial Officer, who joined the Company on July 1, 2015. Tiptree granted Ms. Bell 15,000 restricted shares of Class A common stock with a grant date fair value of $110,400 that were fully vested at grant, but subject to forfeiture if she resigns without Good Reason (as defined in her Employment Agreement described below) prior to July 1, 2016, and 40,761 RSUs with a grant date fair value of $300,000 that will vest in equal annual installments over three years.

Incentive Compensation-Pool DeterminationEXECUTIVE COMPENSATION

(CNG Perspective; Not a Substitute for the Summary Compensation Table)
Our incentive compensation has historically consisted
Name and TitlePerformance YearSalary
($)		Non-Equity Incentive Plan Compensation ($)
Stock
Awards(1)
($)
Option Awards(1) ($)
Other Compensation(2)
Total
($)
Michael G. Barnes
Executive Chairman
2021$600,000$4,057,703$1,512,000—$27,583$6,197,286
2020$600,000$300,000——$25,342$925,342
2019$300,000$1,120,499$611,181$305,591$41,285$2,378,556
Jonathan Ilany
Chief Executive Officer
2021$800,000$4,057,703$1,512,000—$118,813$6,488,516
2020$800,000$300,000——$87,466$1,187,466
2019$600,000$1,680,748$916,772$458,386$81,598$3,737,504
Randy Maultsby(3)
President
2021$350,000$1,250,000$503,995—$7,644$2,111,639
Sandra Bell(4)
Chief Financial Officer
2021$450,000$680,000$340,000—$7,644$1,477,644
2020$450,000$550,000——$7,644$1,007,644
2019$400,000$460,000$115,000—$7,800$982,800
Neil C. Rifkind(5)
VP, General Counsel and Secretary
2021$450,000$680,000$340,000—$7,644$1,477,644
2020$450,000$550,000——$7,644$1,007,644
2019$375,000$460,000$115,000—$7,800$957,800
(1)For Messrs. Barnes, Ilany and Maultsby in performance year 2021, this represents 100,000, 100,000 and 33,333 shares, respectively, issued on November 22, 2021 pursuant to vested PRSUs (the $15 target), with a closing stock price of performance-based annual cash incentive awards$15.12. For all other performance years for Messrs. Barnes, Ilany and annual long-termMaultsby and for all other NEOs, this represents the Par Value of equity incentive awards,grants (RSUs and we continued this practice in 2015.options).

As in 2014, for 2015, the Company continued to use Economic Net Income as a performance measure in determining compensation. Economic Net Income was calculated as the Company’s pre-tax, pre-bonus adjusted net income in substantially the same manner as calculated when the Company was externally managed by Tricadia.

(2)For 2015, the Company established an incentive compensation pool for those in place at the time of the internalization in 2012 equal to approximately 50% of the hypothetical management fees that would have been payable to Tricadia as external manager net of direct and allocated expenses (the “50% Methodology”). After discretionary and contractual bonuses are determined for non-Executive Committee participants in the 50% Methodology compensation pool, subject to adjustment by the CNG Committee, the remaining amount was allocated to the Executive Committee. The dollar amount of the Executive Committee pool was then allocated 55% to be issued in the form of cash, 30% to be issued in the form of fully vested stock and 15% to be issued in the form of time-and performance-based options. The CNG Committee’s methodology for determining the number of shares of stock and options to be granted was agreed upon with the Executive Committee and is described below. Amounts for Ms. Bell and Mr. Rifkind were determinedfor 2021, 2020 and 2019, and for Mr. Maultsby for 2021, this represents premiums paid by the Company to our group health insurance provider under a medical expenses reimbursement plan (the “MERP”). Mr. Barnes’s $27,583 of other compensation in 2021 consists of $7,644 attributable to the MERP, $10,169 attributable to travel reimbursements and $9,770 of reimbursement for taxes associated with such travel reimbursements. Mr. Barnes’s $25,342 of other compensation in 2020 consists of $7,644 attributable to the MERP, $9,173 attributable to travel reimbursements and $8,525 of reimbursement for taxes associated with such travel reimbursements. Mr. Barnes’s $41,285 of other compensation in 2019 consists of $7,800 attributable to the MERP, $19,294 attributable to travel reimbursements and $14,191 of reimbursement for taxes associated with such travel reimbursements. Mr. Ilany’s $118,813 of other compensation in 2021 consists of $7,644 attributable to the MERP, $41,197 attributable to travel reimbursements, $15,499 that the Company paid in connection with maintaining the IT infrastructure in Mr. Ilany’s home office and $54,473 of reimbursements for taxes associated with such travel and IT reimbursements. Mr. Ilany’s $87,446 of other compensation in 2020 consists of $7,664 attributable to the MERP, $23,535 attributable to travel reimbursements, $17,837 that the Company paid in connection with maintaining the IT infrastructure in Mr. Ilany’s home office and $38,450 of reimbursements for taxes associated with such travel and IT reimbursements. Mr. Ilany’s $81,598 of other compensation in 2019 consists of $7,800 attributable to the MERP, $15,832 attributable to travel reimbursements, $15,270 that the Company paid in connection with maintaining the IT infrastructure in Mr. Ilany’s home office and $42,696 of reimbursements for taxes associated with such travel and IT reimbursements.
(3)Mr. Maultsby was appointed our President on July 14, 2021. Mr. Maultsby’s stock award amount for performance year 2021 represent the grant date fair value of the PRSUs granted on August 4, 2021.
(4)Ms. Bell’s stock award amounts for performance years 2021 and 2019 represent the Par Value of the RSU issuances on February 17, 2022 and February 20, 2020, respectively. For the RSU issuance on February 17, 2022, Ms. Bell received matching RSUs that cliff vest after three years and deliver two shares of Tiptree stock for each RSU; as such, the Par Value of the RSU issuance for 2021 was doubled accordingly.
(5)Mr. Rifkind’s stock award amounts for performance years 2021 and 2019 represent the Par Value of the RSU issuances on February 17, 2022 and February 20, 2020, respectively. For the RSU issuance on February 17, 2022, Mr. Rifkind received matching RSUs that cliff vest after three years and deliver two shares of Tiptree stock for each RSU; as such, the Par Value of the RSU issuance for 2021 was doubled accordingly.
37



Use of Independent Compensation Consultant
The CNG Committee engaged CAP to serve as its independent compensation consultant during 2021. CAP received instructions from, and reported to, the CNG Committee on an independent basis. CAP was also authorized by the CNG Committee upon recommendationto share with and request and receive from management specified information in order to prepare for CNG Committee meetings.

The CNG Committee requested CAP’s advice on a variety of matters, including the Executivedesign of our executive compensation program and the compensation opportunities under it, compensation strategy, market comparisons, pay and performance alignment, the advisability of peer benchmarking, executive pay trends, compensation best practices, compensation-related legislative updates and related rulemaking, and compensation plan designs and modifications. The CNG Committee basedmet with CAP, both with and without management present, on several occasions during 2021 with respect to compensation decisions for 2021 performance. The CNG Committee assessed the performanceindependence of the CompanyCAP pursuant to SEC and their individual performance.

Incentive Compensation-Performance-Based Annual Cash Incentive Awards

For 2015, the performance-based annual cash incentive award allocation to the Executive Committee was 55%Nasdaq rules, and concluded that no conflict of the available bonus pool for the Executive Committee (with the remaining 45% in the form of annual long-term equity awards as described below), determined using the 50% Methodology described above.

For 2015, the Executive Committee made an annual cash incentive payout recommendation for the other NEOs, which was approved byinterest exists that would prevent CAP from independently representing the CNG Committee. During 2021, CAP did not provide any services to the Company or its affiliates other than advising the CNG Committee on executive officer compensation.

The CNG Committee does not currently use benchmarking or comparative data in making compensation decisions. In developing recommendations2021, however, the CNG Committee reviewed compensation practices compiled by CAP with respect to the companies that operate in the same industries as the Company to provide a reference point for pay levels and practices, including practices relating to the grant of performance-vesting equity awards.

2021 Company Performance
2021 was one of Tiptree’s best years since its founding in June 2007 and we made meaningful progress on our long-term strategic initiatives and delivered strong shareholder value. Tiptree’s revenues, earnings and total return to shareholders all set records. Our specialty insurer, Fortegra also produced record results, with adjusted return on equity of 22% while growing premiums and equivalents at 32%. In addition, our mortgage and shipping businesses also reported excellent results for the other NEOs,year, benefiting from favorable market conditions. Below is a summary of our 2021 results. Additional information on our 2021 results is contained in our Annual Report on Form 10-K for the Executive Committee consideredyear ended December 31, 2021 filed with the overallSEC.

Full-Year 2021 Summary

($ in thousands, except per share information)FY’21FY’20
Total revenues$1,200,514 $810,301 
Net income (loss) attributable to common stockholders$38,132 $(29,158)
Diluted earnings per share$1.09 $(0.86)
Cash dividends paid per common share$0.16 $0.16 
Return on average equity11.4 %(6.4)%
Non-GAAP: (1)
Adjusted net income$63,869 $51,431 
Adjusted return on average equity16.5 %13.1 %
Adjusted EBITDA$100,776 $4,541 
Book value per share$11.22 $10.90 

•Revenues of $1.2 billion, increased 48.2%, driven by growth in insurance and shipping operations and investment gains in 2021 compared to losses in 2020. Excluding the impact from investment gains and losses, revenues increased 32.9% versus prior year.
38


•Net income of $38.1 million, increased significantly from a net loss in 2020, represented an annualized return on average equity of 11.4%.

•Adjusted net income(1) of $63.9 million, increased 24.2%, reflecting higher earnings in insurance and shipping operations. Adjusted return on average equity(1) of 16.5%, compared to 13.1% in 2020.

•Adjusted EBITDA(1) for the year ended December 31, 2021 was $100.8 million, an increase of $96.2 million from 2020, driven by realized and unrealized gains in 2021 compared to losses in 2020 (primarily Invesque), in addition to the improved operating performance noted above.

•On October 12, 2021, Tiptree announced a $200 million investment in Fortegra from Warburg Pincus, which is expected to close in Q2’22 and will result in an approximate 24% ownership of Tiptree, as well as the individual performance of each

other NEO. For the other NEOs in 2015,business on an aggregate basis, annual cash incentives comprised 61%as converted basis.

Insurance (The Fortegra Group)

($ in thousands)FY’21FY’20
Gross written premiums and premium equivalents$2,194,024 $1,666,942 
Revenues$984,130 $691,061 
Income before taxes$69,857 $26,948 
Return on average equity17.1 %8.1 %
Combined ratio90.6 %91.5 %
Non-GAAP: (1)
Adjusted net income$66,782 $43,423 
Adjusted return on average equity22.2 %15.2 %

•Fortegra’s gross written premiums and premium equivalents increased 31.6% for the year driven by growth in U.S. specialty insurance lines and service contract businesses in U.S. and Europe. As a function of Fortegra’s premium growth, the bonus awardedcombination of unearned premiums and deferred revenues on the balance sheet grew to $1,658.8 million, up $399.1 million, or 31.7%, from 2020.

•Revenues increased 42.4% for the year driven by premium growth and investment gains in 2021 compared to losses in 2020. Excluding the impact of investment gains and losses, revenues increased by 39.5% over 2020.

•For total year 2021, the combined ratio was 90.6%, compared to 91.5% in 2020. Operating and technology efficiencies contributed to an improved expense ratio, while the underwriting ratio remained stable.

•Total year 2021 income before taxes of $69.9 million compared to $26.9 million in the prior year. Return on equity was 17.1% for 2021, as compared to 8.1% in 2020.

•Adjusted net income(1) for 2021 was $66.8 million, up 53.8% from 2020, driven by revenue growth and an improved combined ratio. The adjusted return on average equity(1) was 22.2% for 2021, as compared to 15.2% in 2020.

39


Tiptree Capital

($ in thousands)FY’21FY’20
Revenues$216,384 $119,240 
Income before taxes$45,617 $(30,140)
Return on average equity22.2 %(12.7)%
Non-GAAP: (1)
Adjusted net income$28,197 $33,075 
Adjusted return on average equity16.2 %17.8 %

•Mortgage income before taxes was $28.4 million in 2021, as compared to $31.1 million in 2020, with the remaining 39% consistingdecrease driven by a decline in gain on sale margins, partially offset by higher servicing fees and positive fair value adjustments on the mortgage servicing portfolio. Adjusted return on average equity was 28.8% in 2021.

•Maritime transportation income before taxes was $11.6 million in 2021, as compared to $1.5 million in 2020, with the increase driven by cyclically high dry-bulk charter rates.

•Within Tiptree Capital, our investment in Invesque contributed unrealized gains of RSUs vesting$3.1 million in three equal annual installments.2021 compared to a loss of $67.7 million in 2020.

(1)For a reconciliation to GAAP financials, see “Annex B: Non-GAAP Measures”

2021 Compensation Highlights
Executive Committee
The following describes the annual cash incentive awards made to each member of the Executive Committee in 2015.

NameAnnual Cash Incentive Award
Michael Barnes$605,000 (under TSA)
Jonathan Ilany$907,500
Total$1,512,500

Other NEOs

The following describes the 2015 annual cash incentive awards to the other NEOs.
NameAnnual Cash Incentive Award
Sandra Bell$200,000
Julia Wyatt
$419,250 (under TSA)(1)
Patrick Huvane$225,000 (under ASA)
Neil Rifkind$400,000
Total$1,244,250
Notes
(1) Reflects the payment to Tricadia pursuant to the TSA and may not reflect the amount Ms. Wyatt actually received from Tricadia.

Incentive Compensation-Annual Long-term Equity Incentive Awards

For 2015, the annual long-term equity incentive award allocation to the Executive Committee2021 was 45% of the available bonus poola milestone year for the Executive Committee determined using the 50% Methodology described above, consistingCompany as we achieved record levels of 30% in the form of fully vested stock and 15% in the form of performance and time vested options. The number of shares of stock granted was determined by dividing 30% of each Executive Committee member’s total dollar amount allocated to him under the 2015 incentive compensation pool based on the 50% Methodology described above by $6.5675, which is the 15 calendar day volume weighted average price of the Company's common stock for the period ended on December 31, 2015 (the “VWAP”). The number of stock options was determined by dividing 15% of each Executive Committee member’s total dollar amount allocated to him under the 2015 incentive compensation pool based on the 50% Methodology described above by 25% of $6.5675, the VWAP.

For 2015, the Executive Committee made an annual long-term equity incentive recommendation for the other NEOs, which was approved by the CNG Committee. In developing recommendations for the other NEOs, the Executive Committee considered the overall performance of Tiptree, as well as the individual performance of each other NGO.

Executive Committee

The following table describes the number of shares and options granted to the Executive Committee members.
NameStock Awards (#)Option Awards (#)
Michael Barnes50,247100,495
Jonathan Ilany75,371150,742
Total125,618251,237


The grant of fully vested stock was intended to provide significant alignment of the interests of the Executive Committee with other stockholders by providing the Executive Committee members with the ability to share in the appreciation of the Company’s stock.

The performance-vesting criteria of the stock options were intended to incentivize management to take actions to close the gap between the Company’s GAAP book value per sharefinancial and stock trading price and to compensate the members of the Executive Committee only if they successfully raise the Company’s stock price over the long-term. The stock options also were intended to encourage the retention of the executives through the time-vesting criteria. The exercise price of theperformance. A key performance objective for our performance-based stock options granted on January 4, 2016 and March 10, 2016 is $5.67 and $5.87, respectively, which is the closing stock price on the respective date of grant. Each of the stock options have a ten year term and are subjectin past years was to the following performance- and time-based vesting criteria (each of which must be met for the stock option to vest):

Performance Vesting: Achievement at any time during the option term ofachieve a 20-day volume weighted average stock price that exceedsgreater than the December 31, 2015 book value per share (whichon the date of grant. This hurdle was $8.96).achieved in 2021 for all stock options granted to our Executive Committee.

Compensation of our NEOs is largely driven by the financial and strategic performance of the Company. Total compensation of our NEOs related to fiscal 2021 was approximately $24 million compared to $4.1 million in fiscal 2020. In approving the compensation program for 2021, the CNG Committee considered a number of factors including, but not limited to the responsibilities of the executives’ positions, the executives’ experience and contributions, the competitive marketplace for executive talent and corporate performance. The 2021 increase in total NEO compensation reflects the addition of Mr. Maultsby as President in 2021 (he was not an NEO in 2020) and the significant increase in Adjusted EBITDA in fiscal 2021 versus fiscal 2020.
Time Vesting: 1/3 on
Consistent with Tiptree’s pay for performance philosophy, NEO pay mix is heavily weighted toward variable, performance-based pay, which ties a large portion of compensation to the achievement of our short and long term performance objectives. For 2021, each of the third,Executive Chairman, Chief Executive Officer and President were awarded PRSUs that vest upon Tiptree’s 30 trading day average stock price achieving each of five stock price milestones ranging from $15 to $60, reduced by the aggregate amount of dividends paid, within pre-established determination periods (subject to a catch-up vesting mechanism) occurring on the second, fourth, sixth, eighth and fifthtenth anniversaries of the grant date. This award reflects the CNG Committee’s desire for the Executive Chairman, Chief Executive Officer and President to continue to lead Tiptree for an additional significant number of years and to create significant shareholder value over time. The PRSUs are intended to cover three years of equity compensation for the Executive Chairman, Chief Executive Officer and President, and the CNG Committee does not intend to grant new equity awards to them over the next three years. To date, the first tranche of grant.the PRSUs ($15
40


share price target) vested, resulting in a net issuance of 215,583 shares of Tiptree common stock under the 2017 Plan.

The time-vesting requirementcharts below illustrate the fixed versus variable mix of compensation for our NEOs in 2021. As seen in the illustration below, for 2021, only 8.6% of compensation was fixed for the Executive Committee while 91.4% was variable, of which 46.5% was at risk. Only 21.4% of the options is waived upon a changecompensation of control, an executive’s deaththe other current NEOs at year-end was fixed while 78.6% was variable, of which 31% was at risk.

chart-1e14b4e457b34c97bd3a.jpgchart-f9f7b376b277459dabaa.jpg

Fixed compensation consists of base salary and other guaranteed reimbursements such as travel and information technology reimbursements and the premiums paid for executives under our medical expense reimbursement plan, or disabilityMERP. Variable compensation consists of any award based on performance and CNG Committee determination (including negative discretion) and at-risk compensation consists of any cash or stock award subject to forfeiture.

2021 Executive Compensation Program and Decisions
Our 2021 executive compensation program had three primary elements: base salary, performance-based annual cash incentive awards and long term equity incentive awards. Although each element of compensation described below was considered separately, our CNG Committee made its determinations regarding each individual component of the compensation program in the case of a termination without Cause (as defined below). All unvested stock options will be forfeited on an executive’s voluntary termination or termination for Cause.

For purposescontext of the stock options, “Cause” means any oneaggregate effect on total compensation for each NEO. For the NEOs, incentive compensation for services in a fiscal year was paid or granted, as applicable, in the first quarter of the following:
any event constituting “Cause” as defined in any employment agreement, if any, then in effect between the executive and the Company or any of its affiliates,
the executive's engagement in misconduct which is materially injurious to the Company or any of its affiliates,
the executive's failure to substantially perform his or her duties to the Company or any of its affiliates,
the executive's repeated dishonesty in the performance of his or her duties to the Company or any of its affiliates,
the executive's commission of an act or acts constituting any fraud against, or misappropriation or embezzlement from the Company or any of its affiliates, a crime involving moral turpitude, or an offense that could result in a jail sentence of at least 30 days or
the executive's material breach of any confidentiality or non-competition covenant entered into between the executive and the Company or any of its affiliates.

following year.
Other NEOs

Base Salary

The following table describes the grant date fair valuepurpose of the 2015 annual long-term equity incentive awards, which consistedbase salary is to provide a set amount of RSUscash compensation for each named executive officer that vest annuallyis not variable in three equal installments, granted tonature and is generally competitive with market practices. Base salaries for the NEOs other thanare based on competitive market rates for experienced executives of comparable organizations. The 2021 base salaries for the Executive Committee.NEOs were as follows:

NameRSUs (#)Base Salary
Michael Barnes$600,000
Jonathan Ilany$800,000
Randy Maultsby$350,000
Sandra Bell15,226$450,000
Julia Wyatt30,000 (under TSA)
Patrick Huvane7,613 (under ASA)
Neil Rifkind22,500$450,000
Total75,339$2,650,000

41
Compensation Considerations for 2016


The CNG Committee adopted an incentive compensation program for 2016 that it believes will provide more transparency and greater alignment of management and stockholder’s interest thanEffective January 1, 2022, the 50% Methodology,

which was adopted in 2012 when management was internalized and the Company was privately held. Beginning in 2016, the incentive compensation pool for NEOs will be based on a percentage of Adjusted EBITDA, as presented in the Company’s SEC filings, subject to achievement of an Adjusted EBITDA in 2016 in an amount at least equal to or greater than half of the Adjusted EBITDA in 2015. In addition, beginning in 2016, a high percentage of incentive compensation will consist of variable and at-risk grants of equity instruments rather than solely cash.

Executive Committee

The CNG Committee has established a 2016 incentive compensation pool for the Executive Committee that is equalincreased Messrs. Barnes and Ilany’s annual base salary to up to 5.85% of Adjusted EBITDA, allocated as follows:
Percentage of 2016 Adjusted EBITDA
Michael Barnes
Executive Chairman
2.25%
Jonathan Ilany
Chief Executive Officer
3.60%

The actual dollar amount of incentive compensation paid to each of the Executive Committee members will be determined by the CNG Committee, and is subject to negative and positive discretion, based on such factors as the CNG Committee determines to be relevant, but such discretion shall not result in a payout below 75% of target or above 125% of target.

The incentive compensation pool for the members of the Executive Committee will be allocated 55% in the form of cash, 30% in the form of RSUs with three-year cliff vesting and 15% in the form of performance-vested and time-vested options.

The RSUs will vest on a change of control or an executive’s death or disability. All unvested RSUs will be forfeited on an executive’s voluntary termination or termination for Cause (which has the same definition as in the 2015 stock options described above). The RSUs will continue to vest in the case of a termination without Cause. RSUs will be credited with dividend equivalents from the date of grant through the settlement date.

The stock options will have the same features as the stock options issued in 2015 described above.

Other NEOs

The CNG Committee has established a maximum percentage for the incentive compensation pool for the NEOs other than the Executive Committee of 4.5% of Adjusted EBIDTA. The actual bonus amount for each applicable executive will be determined by the CNG Committee in its discretion, based 50% on the Company’s Adjusted EBITDA relative to the prior year and 50% on the CNG Committee’s qualitative assessment of individual performance for 2016. For Ms. Bell, as required under her employment agreement, 50% of any incentive compensation will be paid in the form of cash and 50% in the form of RSUs that vest in equal annual installments over three years. For each of the other NEOs, 60% of the incentive compensation will be allocated in the form of cash and 40% in the form of RSUs that vest in equal annual installments over three years. Other than annual vesting rather than cliff vesting, the RSUs for the other NEOs will have the same terms as the RSUs that may be granted to the Executive Committee, as described above.

Separation Payments to Mr. Kauffman

On November 10, 2015, Mr. Kauffman resigned as Co-Chief Executive Officer of the Company. Pursuant to a separation agreement, dated as of November 10, 2015, by and among Tiptree Operating Company, LLC$1,000,000 and Mr. Kauffman, he is entitledMaultsby’s annual base salary to payments in the aggregate amount of $6,459,017 in cash and the other benefits provided for in his employment agreement. A payment of $1,250,000 was made in December 2015 and the remaining $5,209,017 will be paid in three equal installments in June 2016, January 2017 and January 2018.$500,000.

Tax Deductibility of NEO Compensation

Section 162(m) of the Internal Revenue Code (“Section 162(m)”) generally imposes a $1 million limit on the deduction that a company may claim in any tax year with respect to compensation paid to each of its Chief Executive Officer and three other NEOs (other than the Chief Financial Officer). Certain types of performance-based compensation may qualify as exempt from the $1 million limit. Performance-based compensation generally includes only those payments that are contingent upon the achievement of pre-established performance objectives and excludes any fixed or guaranteed payments. One of the factors that we may consider in structuring and determining the compensation for our NEOs is the deductibility of such compensation under Section 162(m) to the extent applicable. However, this consideration is balanced with our primary goal of structuring compensation programs to attract, reward, motivate and retain highly talented executives. Our CNG Committee may approve compensation arrangements for our NEOs that are not fully deductible under Section 162(m) after taking into account several factors, including our ability to utilize deductions based on projected taxable income, and specifically reserves the right to do so.

Response to Say on Pay Advisory Vote and Stockholder Feedback

At our 2014 Annual Meeting of Stockholders, our advisory vote to approve compensation of our NEOs received the support of 99.87% of the votes cast. Our management met with several of our largest stockholders in 2015 and communicated stockholder feedback and comments to our CNG Committee, who considered that information in making 2015 compensation decisions.

COMPENSATION COMMITTEE REPORT

The CNG Committee has reviewed and discussed with management the preceding Compensation Discussion and Analysis contained in this proxy statement. Based on its review and discussions with management, the Committee recommended to the Board of Directors that the Compensation Discussion and Analysis be included in Tiptree’s proxy statement on Schedule 14A filed with the SEC.
Submitted by the Compensation Committee
Richard A. Price, Chair
Lesley Goldwasser
John E. Mack
Bradley E. Smith

The foregoing report shall not be deemed incorporated by reference by any general statement incorporating by
reference this proxy statement into any filing under the Securities Act or under the Exchange Act, except to the extent that we specifically incorporate this information by reference, and shall not otherwise be deemed filed under the Securities Act and/or Exchange Act.













EXECUTIVE COMPENSATION
(CNG Perspective; Not a Substitute for the Summary Compensation Table)
Name and TitlePerformance YearSalary
($)		Non-Equity Incentive Plan Compensation ($)
Stock
Awards(1)
($)
Option Awards(1) ($)
Other Compensation(2)
Total
($)
Michael G. Barnes
Executive Chairman
2021$600,000$4,057,703$1,512,000—$27,583$6,197,286
2020$600,000$300,000——$25,342$925,342
2019$300,000$1,120,499$611,181$305,591$41,285$2,378,556
Jonathan Ilany
Chief Executive Officer
2021$800,000$4,057,703$1,512,000—$118,813$6,488,516
2020$800,000$300,000——$87,466$1,187,466
2019$600,000$1,680,748$916,772$458,386$81,598$3,737,504
Randy Maultsby(3)
President
2021$350,000$1,250,000$503,995—$7,644$2,111,639
Sandra Bell(4)
Chief Financial Officer
2021$450,000$680,000$340,000—$7,644$1,477,644
2020$450,000$550,000——$7,644$1,007,644
2019$400,000$460,000$115,000—$7,800$982,800
Neil C. Rifkind(5)
VP, General Counsel and Secretary
2021$450,000$680,000$340,000—$7,644$1,477,644
2020$450,000$550,000——$7,644$1,007,644
2019$375,000$460,000$115,000—$7,800$957,800
(1)For Messrs. Barnes, Ilany and Maultsby in performance year 2021, this represents 100,000, 100,000 and 33,333 shares, respectively, issued on November 22, 2021 pursuant to vested PRSUs (the $15 target), with a closing stock price of $15.12. For all other performance years for Messrs. Barnes, Ilany and Maultsby and for all other NEOs, this represents the Par Value of equity grants (RSUs and options).
(2)For Ms. Bell and Mr. Rifkind for 2021, 2020 and 2019, and for Mr. Maultsby for 2021, this represents premiums paid by the Company to our group health insurance provider under a medical expenses reimbursement plan (the “MERP”). Mr. Barnes’s $27,583 of other compensation in 2021 consists of $7,644 attributable to the MERP, $10,169 attributable to travel reimbursements and $9,770 of reimbursement for taxes associated with such travel reimbursements. Mr. Barnes’s $25,342 of other compensation in 2020 consists of $7,644 attributable to the MERP, $9,173 attributable to travel reimbursements and $8,525 of reimbursement for taxes associated with such travel reimbursements. Mr. Barnes’s $41,285 of other compensation in 2019 consists of $7,800 attributable to the MERP, $19,294 attributable to travel reimbursements and $14,191 of reimbursement for taxes associated with such travel reimbursements. Mr. Ilany’s $118,813 of other compensation in 2021 consists of $7,644 attributable to the MERP, $41,197 attributable to travel reimbursements, $15,499 that the Company paid in connection with maintaining the IT infrastructure in Mr. Ilany’s home office and $54,473 of reimbursements for taxes associated with such travel and IT reimbursements. Mr. Ilany’s $87,446 of other compensation in 2020 consists of $7,664 attributable to the MERP, $23,535 attributable to travel reimbursements, $17,837 that the Company paid in connection with maintaining the IT infrastructure in Mr. Ilany’s home office and $38,450 of reimbursements for taxes associated with such travel and IT reimbursements. Mr. Ilany’s $81,598 of other compensation in 2019 consists of $7,800 attributable to the MERP, $15,832 attributable to travel reimbursements, $15,270 that the Company paid in connection with maintaining the IT infrastructure in Mr. Ilany’s home office and $42,696 of reimbursements for taxes associated with such travel and IT reimbursements.
(3)Mr. Maultsby was appointed our President on July 14, 2021. Mr. Maultsby’s stock award amount for performance year 2021 represent the grant date fair value of the PRSUs granted on August 4, 2021.
(4)Ms. Bell’s stock award amounts for performance years 2021 and 2019 represent the Par Value of the RSU issuances on February 17, 2022 and February 20, 2020, respectively. For the RSU issuance on February 17, 2022, Ms. Bell received matching RSUs that cliff vest after three years and deliver two shares of Tiptree stock for each RSU; as such, the Par Value of the RSU issuance for 2021 was doubled accordingly.
(5)Mr. Rifkind’s stock award amounts for performance years 2021 and 2019 represent the Par Value of the RSU issuances on February 17, 2022 and February 20, 2020, respectively. For the RSU issuance on February 17, 2022, Mr. Rifkind received matching RSUs that cliff vest after three years and deliver two shares of Tiptree stock for each RSU; as such, the Par Value of the RSU issuance for 2021 was doubled accordingly.
37



Use of Independent Compensation Consultant
The CNG Committee engaged CAP to serve as its independent compensation consultant during 2021. CAP received instructions from, and reported to, the CNG Committee on an independent basis. CAP was also authorized by the CNG Committee to share with and request and receive from management specified information in order to prepare for CNG Committee meetings.

The CNG Committee requested CAP’s advice on a variety of matters, including the design of our executive compensation program and the compensation opportunities under it, compensation strategy, market comparisons, pay and performance alignment, the advisability of peer benchmarking, executive pay trends, compensation best practices, compensation-related legislative updates and related rulemaking, and compensation plan designs and modifications. The CNG Committee met with CAP, both with and without management present, on several occasions during 2021 with respect to compensation decisions for 2021 performance. The CNG Committee assessed the independence of CAP pursuant to SEC and Nasdaq rules, and concluded that no conflict of interest exists that would prevent CAP from independently representing the CNG Committee. During 2021, CAP did not provide any services to the Company or its affiliates other than advising the CNG Committee on executive officer compensation.

The CNG Committee does not currently use benchmarking or comparative data in making compensation decisions. In 2021, however, the CNG Committee reviewed compensation practices compiled by CAP with respect to the companies that operate in the same industries as the Company to provide a reference point for pay levels and practices, including practices relating to the grant of performance-vesting equity awards.

2021 Company Performance
2021 was one of Tiptree’s best years since its founding in June 2007 and we made meaningful progress on our long-term strategic initiatives and delivered strong shareholder value. Tiptree’s revenues, earnings and total return to shareholders all set records. Our specialty insurer, Fortegra also produced record results, with adjusted return on equity of 22% while growing premiums and equivalents at 32%. In addition, our mortgage and shipping businesses also reported excellent results for the year, benefiting from favorable market conditions. Below is a summary of our 2021 results. Additional information on our 2021 results is contained in our Annual Report on Form 10-K for the year ended December 31, 2021 filed with the SEC.

Full-Year 2021 Summary

($ in thousands, except per share information)FY’21FY’20
Total revenues$1,200,514 $810,301 
Net income (loss) attributable to common stockholders$38,132 $(29,158)
Diluted earnings per share$1.09 $(0.86)
Cash dividends paid per common share$0.16 $0.16 
Return on average equity11.4 %(6.4)%
Non-GAAP: (1)
Adjusted net income$63,869 $51,431 
Adjusted return on average equity16.5 %13.1 %
Adjusted EBITDA$100,776 $4,541 
Book value per share$11.22 $10.90 

•Revenues of $1.2 billion, increased 48.2%, driven by growth in insurance and shipping operations and investment gains in 2021 compared to losses in 2020. Excluding the impact from investment gains and losses, revenues increased 32.9% versus prior year.
38


•Net income of $38.1 million, increased significantly from a net loss in 2020, represented an annualized return on average equity of 11.4%.

•Adjusted net income(1) of $63.9 million, increased 24.2%, reflecting higher earnings in insurance and shipping operations. Adjusted return on average equity(1) of 16.5%, compared to 13.1% in 2020.

•Adjusted EBITDA(1) for the year ended December 31, 2021 was $100.8 million, an increase of $96.2 million from 2020, driven by realized and unrealized gains in 2021 compared to losses in 2020 (primarily Invesque), in addition to the improved operating performance noted above.

•On October 12, 2021, Tiptree announced a $200 million investment in Fortegra from Warburg Pincus, which is expected to close in Q2’22 and will result in an approximate 24% ownership of the business on an as converted basis.

Insurance (The Fortegra Group)

($ in thousands)FY’21FY’20
Gross written premiums and premium equivalents$2,194,024 $1,666,942 
Revenues$984,130 $691,061 
Income before taxes$69,857 $26,948 
Return on average equity17.1 %8.1 %
Combined ratio90.6 %91.5 %
Non-GAAP: (1)
Adjusted net income$66,782 $43,423 
Adjusted return on average equity22.2 %15.2 %

•Fortegra’s gross written premiums and premium equivalents increased 31.6% for the year driven by growth in U.S. specialty insurance lines and service contract businesses in U.S. and Europe. As a function of Fortegra’s premium growth, the combination of unearned premiums and deferred revenues on the balance sheet grew to $1,658.8 million, up $399.1 million, or 31.7%, from 2020.

•Revenues increased 42.4% for the year driven by premium growth and investment gains in 2021 compared to losses in 2020. Excluding the impact of investment gains and losses, revenues increased by 39.5% over 2020.

•For total year 2021, the combined ratio was 90.6%, compared to 91.5% in 2020. Operating and technology efficiencies contributed to an improved expense ratio, while the underwriting ratio remained stable.

•Total year 2021 income before taxes of $69.9 million compared to $26.9 million in the prior year. Return on equity was 17.1% for 2021, as compared to 8.1% in 2020.

•Adjusted net income(1) for 2021 was $66.8 million, up 53.8% from 2020, driven by revenue growth and an improved combined ratio. The adjusted return on average equity(1) was 22.2% for 2021, as compared to 15.2% in 2020.

39


Tiptree Capital

($ in thousands)FY’21FY’20
Revenues$216,384 $119,240 
Income before taxes$45,617 $(30,140)
Return on average equity22.2 %(12.7)%
Non-GAAP: (1)
Adjusted net income$28,197 $33,075 
Adjusted return on average equity16.2 %17.8 %

•Mortgage income before taxes was $28.4 million in 2021, as compared to $31.1 million in 2020, with the decrease driven by a decline in gain on sale margins, partially offset by higher servicing fees and positive fair value adjustments on the mortgage servicing portfolio. Adjusted return on average equity was 28.8% in 2021.

•Maritime transportation income before taxes was $11.6 million in 2021, as compared to $1.5 million in 2020, with the increase driven by cyclically high dry-bulk charter rates.

•Within Tiptree Capital, our investment in Invesque contributed unrealized gains of $3.1 million in 2021 compared to a loss of $67.7 million in 2020.

(1)For a reconciliation to GAAP financials, see “Annex B: Non-GAAP Measures”

2021 Compensation Highlights
2021 was a milestone year for the Company as we achieved record levels of financial and stock price performance. A key performance objective for our performance-based stock options granted in past years was to achieve a 20-day volume weighted average stock price greater than the book value per share on the date of grant. This hurdle was achieved in 2021 for all stock options granted to our Executive Committee.
Compensation of our NEOs is largely driven by the financial and strategic performance of the Company. Total compensation of our NEOs related to fiscal 2021 was approximately $24 million compared to $4.1 million in fiscal 2020. In approving the compensation program for 2021, the CNG Committee considered a number of factors including, but not limited to the responsibilities of the executives’ positions, the executives’ experience and contributions, the competitive marketplace for executive talent and corporate performance. The 2021 increase in total NEO compensation reflects the addition of Mr. Maultsby as President in 2021 (he was not an NEO in 2020) and the significant increase in Adjusted EBITDA in fiscal 2021 versus fiscal 2020.
Consistent with Tiptree’s pay for performance philosophy, NEO pay mix is heavily weighted toward variable, performance-based pay, which ties a large portion of compensation to the achievement of our short and long term performance objectives. For 2021, each of the Executive Chairman, Chief Executive Officer and President were awarded PRSUs that vest upon Tiptree’s 30 trading day average stock price achieving each of five stock price milestones ranging from $15 to $60, reduced by the aggregate amount of dividends paid, within pre-established determination periods (subject to a catch-up vesting mechanism) occurring on the second, fourth, sixth, eighth and tenth anniversaries of the grant date. This award reflects the CNG Committee’s desire for the Executive Chairman, Chief Executive Officer and President to continue to lead Tiptree for an additional significant number of years and to create significant shareholder value over time. The PRSUs are intended to cover three years of equity compensation for the Executive Chairman, Chief Executive Officer and President, and the CNG Committee does not intend to grant new equity awards to them over the next three years. To date, the first tranche of the PRSUs ($15
40


share price target) vested, resulting in a net issuance of 215,583 shares of Tiptree common stock under the 2017 Plan.

The charts below illustrate the fixed versus variable mix of compensation for our NEOs in 2021. As seen in the illustration below, for 2021, only 8.6% of compensation was fixed for the Executive Committee while 91.4% was variable, of which 46.5% was at risk. Only 21.4% of the compensation of the other current NEOs at year-end was fixed while 78.6% was variable, of which 31% was at risk.

chart-1e14b4e457b34c97bd3a.jpgchart-f9f7b376b277459dabaa.jpg

Fixed compensation consists of base salary and other guaranteed reimbursements such as travel and information technology reimbursements and the premiums paid for executives under our medical expense reimbursement plan, or MERP. Variable compensation consists of any award based on performance and CNG Committee determination (including negative discretion) and at-risk compensation consists of any cash or stock award subject to forfeiture.

2021 Executive Compensation Program and Decisions
Our 2021 executive compensation program had three primary elements: base salary, performance-based annual cash incentive awards and long term equity incentive awards. Although each element of compensation described below was considered separately, our CNG Committee made its determinations regarding each individual component of the compensation program in the context of the aggregate effect on total compensation for each NEO. For the NEOs, incentive compensation for services in a fiscal year was paid or granted, as applicable, in the first quarter of the following year.

Base Salary

The purpose of base salary is to provide a set amount of cash compensation for each named executive officer that is not variable in nature and is generally competitive with market practices. Base salaries for the NEOs are based on competitive market rates for experienced executives of comparable organizations. The 2021 base salaries for the NEOs were as follows:

NameBase Salary
Michael Barnes$600,000
Jonathan Ilany$800,000
Randy Maultsby$350,000
Sandra Bell$450,000
Neil Rifkind$450,000
Total$2,650,000

41


Effective January 1, 2022, the CNG Committee has increased Messrs. Barnes and Ilany’s annual base salary to $1,000,000 and Mr. Maultsby’s annual base salary to $500,000.

Incentive Compensation-Pool Determination
In addition to the PRSUs granted to each of the Executive Chairman, Chief Executive Officer and President, for 2021 the CNG Committee established a 2021 cash incentive compensation pool for the Executive Committee equal to 7.0% of Adjusted EBITDA prior to the payment of the incentive compensation of the Executive Committee, and allocated 3.5% to Michael Barnes, Executive Chairman and 3.5% to Jonathan Ilany, Chief Executive Officer.

Incentive Compensation-Pool Determination — Other NEOs

For 2021, the CNG Committee established an incentive compensation pool for the NEOs other than the Executive Committee of up to a maximum of 4.5% of Adjusted EBITDA prior to payment of the incentive compensation of the Executive Committee. For the other NEOs, except Mr. Maultsby, this pool was allocated 80% in cash and 20% in the form of matching RSUs that cliff vest after three years and deliver two shares of Tiptree stock for each RSU. In 2021, Mr. Maultsby was granted 500,000 PRSUs and a cash bonus.

For 2021, the CNG Committee awarded aggregate incentive compensation to the NEOs other than the Executive Committee in an aggregate amount of approximately $4.3 million or approximately 3.7% of Adjusted EBITDA prior to payment of the incentive compensation of the Executive Committee, which was less than the maximum. The actual bonus amount for each applicable executive was determined by the CNG Committee in its discretion in consultation with the Executive Committee, based 50% on the Company’s Adjusted EBITDA relative to the prior year and 50% on the CNG Committee’s qualitative assessment of individual performance for 2021 considering the NEO’s role, leadership responsibilities and retention considerations.

Incentive Compensation-Performance-Based Annual Cash Incentive Awards — Executive Committee and Other NEOs

For 2021, the performance-based annual cash incentive award allocation to the Executive Committee was as follows:    
NameAnnual Cash Incentive Award
Michael Barnes$4,057,703
Jonathan Ilany$4,057,703
Total$8,115,406

For 2021, the performance-based annual cash incentive award allocation to the other NEOs were as follows:

NameAnnual Cash Incentive Award
Randy Maultsby$1,250,000
Sandra Bell$680,000
Neil Rifkind$680,000
Total$2,610,000

Tax Deductibility of NEO Compensation
Section 162(m) of the Code (“Section 162(m)”) imposes a $1 million limit on the deduction that a company could claim in any tax year with respect to compensation paid to certain of its current and former executive officers, subject to certain limited exceptions with respect to certain compensation arrangements in effect on November 2,
42


2017. Our CNG Committee has and may approve compensation arrangements for our NEOs that are not fully deductible under Section 162(m) and specifically reserves the right to do so.
Response to Say on Pay Advisory Vote and Stockholder Feedback
At our 2020 Annual Meeting of Stockholders, our advisory vote to approve compensation of our NEOs received the support of 80.22% of the votes cast. Our management met with several of our largest stockholders in 2021 and communicated stockholder feedback and comments to our CNG Committee, who considered that information in making 2021 compensation decisions.


COMPENSATION COMMITTEE REPORT

The CNG Committee has reviewed and discussed with management the preceding Compensation Discussion and Analysis contained in this proxy statement. Based on its review and discussions with management, the Committee recommended to the Board of Directors that the Compensation Discussion and Analysis be included in Tiptree’s proxy statement on Schedule 14A filed with the SEC.
Submitted by the Compensation Committee
Dominique Mielle, Chair
Lesley Goldwasser
Paul M. Friedman
Bradley E. Smith

The foregoing report shall not be deemed incorporated by reference by any general statement incorporating by reference this proxy statement into any filing under the Securities Act or under the Exchange Act, except to the extent that we specifically incorporate this information by reference, and shall not otherwise be deemed filed under the Securities Act and/or Exchange Act.


EXECUTIVE COMPENSATION

Summary Compensation
The following table sets forth information regarding the compensation approvedpaid to be paidor earned by our NEOs for services in 2021, 2020 and 2019, as applicable to each NEO, in the format required by the SEC. The footnotes to these tables provide information to explain the values presented in the tables and are an important part of our disclosures.
We have included a separate table in “Compensation Discussion and Analysis—Named Executive Officers” as supplemental disclosure, which table shows the base salary and incentive compensation awarded to our NEOs for their performance in 2015, 20142021, 2020 and 2013.2019, as applicable to each NEO, in the manner that it was considered by the CNG Committee.

Except where otherwise noted, the equity awards shown in our Summary Compensation Table and Grants of Plan-Based Awards table for the fiscal years 2020 and 2019 were granted in February 2020 and February 2019, respectively, for services performed in 2019 and 2018, respectively. Our CNG Committee did not grant any equity awards in 2021 for services performed in 2020.
43



The only equity awards granted in 2021 were the PRSUs granted to our Executive Chairman, Chief Executive Officer and President, which reflect the CNG Committee’s desire for such executives to continue to lead Tiptree for an additional significant number of years and to create significant shareholder value over time. The PRSUs are intended to cover three years of equity compensation for the Executive Chairman, Chief Executive Officer and President, and the CNG Committee does not intend to grant new equity awards to them over the next three years.

Summary Compensation Table
Name and Title Year 
Salary or Service Fees Paid to Tricadia
($)
 
Bonus
($)
 
Stock
Awards(1)
($)
 
Option Awards ($)(1)
 
All Other
Compensation
($)
 
Total
($)
Michael G. Barnes(2)
Executive Chairman
 2015 $100,000
 $605,000
 $285,814
 $263,525
   $1,254,339
 2014 $100,000
 $—
 $1,385,148
 $—
 $—
 $1,485,148
 2013 $100,000
 $—
 $1,620,003
 $—
 $—
 $1,720,003
Jonathan Ilany(3)
Chief Executive Officer
 2015 $350,000
 $907,500
 $428,724
 $395,286
 $32,476
 $2,113,986
 2014 $87,500
 $—
 $230,100
 $—
 $—
 $317,600
Geoffrey Kauffman(4)
Former Co-Chief Executive Officer
 2015 $306,250
 $—
 $—
 $—
 $1,250,000
 $1,556,250
 2014 $350,000
 $1,585,479
 $461,711
 $—
 $—
 $2,397,190
 2013 $350,000
 $1,824,832
 $636,995
 $—
 $—
 $2,811,827
Sandra Bell(5)
Chief Financial Officer
 2015 $200,000
 $200,000
 $496,732
   $—
 $896,732
Richard Claiden(6)
Former Chief Financial Officer
 2015 $214,894
 $—
 $—
 $—
 $—
 $214,894
Julia Wyatt(7)
Chief Operating Officer
 2015 $350,000
 $419,250
 $170,100
 $—
   $939,350
 2014 $350,000
 $372,250
 $115,050
 $—
 $—
 $837,300
 2013 $350,000
 $414,500
 $50,002
 $—
 $—
 $814,502
Neil C. Rifkind(8)
Vice President, General Counsel and Secretary
 2015 $375,000
 $400,000
 $127,575
 $—
 $—
 $902,575
 2014 $375,000
 $375,000
 $126,555
 $—
 $—
 $876,555
 2013 $187,500
 $125,000
 $15,000
 $—
 $—
 $327,500
Patrick Huvane(9)
Chief Accounting Officer
 2015 $193,750
 $225,000
 $43,166
 $—
 $—
 $461,916
 2014 $175,000
 $225,000
 $—
 $—
 $—
 $400,000
 2013 $175,000
 $269,500
 $5,395
 $—
 $—
 $449,895
Name and TitleYearSalary($)Bonus ($)
Stock
Awards
($)(1)
Option Awards ($)(1)
Non-Equity Incentive Plan Compensation(2)
All Other
Compensation
($)(3)
Total ($)
Michael G. Barnes(4)
Executive Chairman
2021$600,000—$4,192,400$—$4,057,703$27,583$8,877,686
2020$600,000—$616,649$311,337$300,000$25,342$1,853,328
2019$300,000—$282,720$152,723$1,120,499$41,285$1,897,227
Jonathan Ilany(5)
Chief Executive Officer
2021$800,000—$4,192,400$—$4,057,703$118,813$9,168,916
2020$800,000—$924,977$467,005$300,000$87,466$2,579,448
2019$600,000—$424,077$229,085$1,680,748$81,598$3,015,508
Randy Maultsby(6)
     President
2021$350,000—$1,397,466—$1,250,000$7,644$3,005,110
Sandra Bell(7)
Chief Financial Officer
2021$450,000—$——$680,000$7,644$1,137,644
2020$450,000—$116,029—$550,000$7,644$1,123,673
2019$400,000—$104,066—$460,000$7,800$971,866
Neil C. Rifkind(8)
VP, General Counsel and Secretary
2021$450,000—$——$680,000$7,644$1,137,644
2020$450,000—$116,029—$550,000$7,644$1,123,673
2019$375,000—$109,024—$460,000$7,800$951,824
 
(1)See Note 21 to the Company’s Consolidated Financial Statements included in the Company’s 2015 Annual Report on Form 10-K. Stock and option award values are based on the grant date fair value computed in accordance with FASB ASC Topic 718, with the option awards computed using a Black-Scholes valuation model assuming 50% volatility. In accordance with SEC rules, estimates of forfeitures related to service-based conditions have been disregarded.
(2)Mr. Barnes does not receive compensation directly from Tiptree. Tiptree pays $100,000 per year plus incentive compensation to Tricadia for Mr. Barnes’ services as Executive Chairman of Tiptree under a TSA between Tiptree and Tricadia. See “Certain Relationships and Related Transactions — Transactions with Related Persons — Transition Services Agreement.” Stock and stock option award amount represents the December 31 closing price value of such shares and stock options received by Tricadia as incentive compensation approved by the CNG Committee for Mr. Barnes’ services as Executive Chairman under the TSA. Mr. Barnes is a partner in Tricadia and the December 31 closing price value of shares received by Mr. Barnes from Tricadia in a distribution of shares of Class A common stock in accordance with Mr. Barnes’ interests in Tricadia was $544,739 for 2014 and $618,237 for 2013. The shares and options received by Tricadia in 2015 have not been distributed so all are beneficially attributed to Mr. Barnes. Mr. Barnes disclaims beneficial ownership of these securities except to the extent of his pecuniary interest.
(3)Mr. Ilany joined Tiptree as Executive Vice President, Head of Mortgage Finance and Asset Management on October 1, 2014. The stock and stock option award amount in 2015 represents the December 31 closing price value of such shares and stock options; the stock award in 2014 consists of RSUs granted January 5, 2015 that vest over three years. The $32,476 of other compensation consists of travel reimbursements and taxes associated with such reimbursements.
(4)Mr. Kauffman’s 2015 salary represents the amount he earned from January 1, 2015 to November 10, 2015, the date of his resignation. All other compensation for 2015 represents the amount paid in 2015 pursuant to a separation agreement, dated as of November 10, 2015. The $1,250,000 of other compensation consists of a severance payment to Mr. Kauffman that was made in December 2015. The remaining $5,209,017 of Mr. Kauffman’s severance payment will be paid in three equal installments in each of June 2016, January 2017 and January 2018.

(1)Amounts in this column represent the aggregate grant date fair value of PRSUs, RSUs and stock options, computed in accordance with FASB ASC Topic 718. In 2021, the only stock awards granted were 1,500,000 PRSUs granted to each of Messrs. Barnes and Ilany and 500,000 PRSUs granted to Mr. Maultsby. RSUs are valued using the closing price of our common stock on the grant date. We use the Black-Scholes model assuming 50% volatility to estimate our compensation cost for stock option awards. The fair value of the PRSUs was estimated on the date of grant using a Black-Scholes-Merton option pricing formula embedded within a Monte Carlo model used to simulate the future stock prices of Tiptree, which assumes that the market requirement is achieved. For more detail, including the underlying valuation assumptions for PRSUs and stock option awards, please see Note 19, Stock Based Compensation, to our consolidated financial statements in our 2021 Annual Report on Form 10-K. Pursuant to SEC rules, the amounts shown exclude the impact of estimated forfeitures related to service-based vesting conditions.

(5)Ms. Bell joined Tiptree as Chief Financial Officer on July 1, 2015. Her stock award amount in 2015 represents the grant date value of the shares and RSU issuance on July 1, 2015 and the RSU issuance on January 4, 2016. All RSUs vest equally over three years of the grant date.
(6)Mr. Claiden joined Tiptree as Chief Financial Officer on January 1, 2015 and resigned effective February 28, 2015. Mr. Claiden remained as a part time employee of Tiptree as a consulting senior advisor on accounting and financial reporting matters from March 1, 2015 to December 31, 2015.
(7)For 2013, 2014 and 2015, Ms. Wyatt did not receive cash compensation directly from the Company. Tiptree pays Tricadia for Ms. Wyatt’s services and certain other finance/accounting personnel under the TSA between Tiptree and Tricadia. See “Certain Relationships and Related Transactions — Transactions with Related Persons — Transition Services Agreement.” The amounts listed under her salary and bonus reflect the payment to Tricadia pursuant to the TSA and may not reflect the amounts she actually received from Tricadia. Her stock award represents the grant date value of shares on December 31, 2013 and the RSU issuances on January 4, 2016 and January 5, 2015. All RSUs vest equally over three years of the grant date. Her stock award amount excludes shares of Class A common stock received by Ms. Wyatt as a limited partner in Tricadia in a pro rata distribution in accordance with Ms. Wyatt’s interests in Tricadia. As of January 1, 2016, Ms. Wyatt became an employee of a subsidiary of the Company.
(8)Mr. Rifkind was appointed Vice President, General Counsel and Secretary on July 8, 2013. His stock award represents the grant date value of the RSU issuances on January 4, 2016 and January 5, 2015. All RSUs vest equally over three years of the grant date.
(9)Mr. Huvane does not receive cash compensation directly from the Company. Tiptree pays BackOffice Services Group, Inc. (“BOSG”) for Mr. Huvane’s services and certain other back office, administrative and accounting services. See “Certain Relationships and Related Transactions — Transactions with Related Persons — Transition Services Agreement.” The amounts listed under his salary and bonus reflect the payment to BOSG and may not reflect the amounts he actually received from BOSG. His stock award represents the grant date value of the RSU issuance January 4, 2016, which vest equally over three years of the grant date.

(2)Represents the dollar value of cash incentive awards earned in the performance year but paid in the first quarter of the following year.
(3)For Ms. Bell and Mr. Rifkind for 2021, 2020 and 2019, and for Mr. Maultsby for 2021, this represents premiums paid by the Company to our group health insurance provider under a medical expenses reimbursement plan (the “MERP”). Mr. Barnes’s $27,583 of other compensation in 2021 consists of $7,644 attributable to the MERP, $10,169 attributable to travel reimbursements and $9,770 of reimbursement for taxes associated with such travel reimbursements. Mr. Barnes’s $25,342 of other compensation in 2020 consists of $7,644 attributable to the MERP, $9,173 attributable to travel reimbursements and $8,525 of reimbursement for taxes associated with such travel reimbursements. Mr. Barnes’s $41,285 of other compensation in 2019 consists of $7,800 attributable to the MERP, $19,294 attributable to travel reimbursements and $14,191 of reimbursement for taxes associated with such travel reimbursements. Mr. Ilany’s $118,813 of other compensation in 2021 consists of $7,644 attributable to the MERP, $41,197 attributable to travel reimbursements, $15,499 that the Company paid in connection with maintaining the IT infrastructure in Mr. Ilany’s home office and $54,473 of reimbursements for taxes associated with such travel and IT reimbursements. Mr. Ilany’s $87,446 of other compensation in 2020 consists of $7,664 attributable to the MERP, $23,535 attributable to travel reimbursements, $17,837 that the Company paid in connection with maintaining the IT infrastructure in Mr. Ilany’s home office and $38,450 of reimbursements for taxes associated with such travel and IT reimbursements. Mr. Ilany’s $81,598 of other compensation in 2019 consists of $7,800 attributable to the MERP, $15,832 attributable to travel reimbursements, $15,270 that the Company paid in connection with maintaining the IT infrastructure in Mr. Ilany’s home office and $42,696 of reimbursements for taxes associated with such travel and IT reimbursements.
44


(4)Mr. Barnes’s stock award amount in 2019 and 2020 represents the grant date fair value of the RSUs and stock options granted to him on February 26, 2019 and February 20, 2020, respectively. His 2019 and 2020 RSUs cliff vest on February 15, 2022 and 2023, respectively. The stock award amount in 2021 represent the 1,500,000 PRSUs granted on August 4, 2021. A portion of the total number of PRSUs subject to the award will generally vest upon achievement of each of five Tiptree share price target milestones ranging from $15 to $60 (adjusted for dividends paid) prior to the tenth anniversary of the date of grant, subject to his continued employment with Tiptree.
(5)Mr. Ilany’s stock award amount in 2019 and 2020 represents the grant date fair value of the RSUs and stock options granted to him on February 26, 2019 and February 20, 2020, respectively. His 2019 and 2020 RSUs cliff vest on February 15, 2022 and 2023, respectively. The stock award amount in 2021 represent the 1,500,000 PRSUs granted on August 4, 2021. A portion of the total number of PRSUs subject to the award will generally vest upon achievement of each of five Tiptree share price target milestones ranging from $15 to $60 (adjusted for dividends paid) prior to the tenth anniversary of the date of grant, subject to his continued employment with Tiptree.
(6)Mr. Maultsby was appointed as our President on July 14, 2021. The stock award amount in 2021 represents the 500,000 PRSUs granted on August 4, 2021. A portion of the total number of PRSUs subject to the award will generally vest upon achievement of each of five Tiptree share price target milestones ranging from $15 to $60 (adjusted for dividends paid) prior to the tenth anniversary of the date of grant, subject to his continued employment with Tiptree.
(7)Ms. Bell’s stock award amount in 2019 and 2020 represents the grant date fair value of RSUs granted to her on February 26, 2019 and February 20, 2020, respectively. Her unvested RSUs vest ratably over three years on February 15 of each successive year, respectively.
(8)Mr. Rifkind’s stock award amount in 2019 and 2020 represents the grant date fair value of RSUs granted to him on February 26, 2019 and February 20, 2020, respectively. His unvested RSUs vest ratably over three years on February 15 of each successive year, respectively.


Grants of Plan-Based Awards
The following table provides additional information about non-equity and equity-based awards granted to our NEOs during the year ended December 31, 2021:
Estimated Future Payouts Under Non-Equity Incentive Plan Awards(1)
NameThresholdTargetMaximumGrant Date
Estimated Future
Payouts under
Equity Incentive
Plan Awards(2)
Grant Date Fair Value(3) ($)
Michael G. Barnes—$4,057,703—8/4/20211,500,000$4,192,400
Jonathan Ilany—$4,057,703—8/4/20211,500,000$4,192,400
Randy Maultsby———8/4/2021500,000$1,397,466
Sandra Bell—————$—
Neil C. Rifkind—————$—

(1)For Messrs. Barnes and Ilany, the $ figures in the table above represent the incentive compensation pool for the Executive Committee based on a percentage of 2020 Adjusted EBITDA which was paid in the first quarter of 2021. The aggregate incentive compensation pool for our executive officers other than the Executive Committee (currently, Ms. Bell and Messrs. Maultsby and Rifkind), is subject to a cap of 4.5% of Adjusted EBITDA prior to the payment of the incentive compensation of the Executive Committee. The actual amounts granted to Ms. Bell and Messrs. Maultsby and Rifkind were subject to the discretion of the Executive Committee and, as such, do not have calculable threshold, target or maximum estimated payouts.
(2)In 2021, the only stock awards granted were 1,500,000 PRSUs granted to each of Messrs. Barnes and Ilany and 500,000 PRSUs granted to Mr. Maultsby on August 4, 2021. A portion of the total number of PRSUs subject to the award will generally vest upon achievement of each of five Tiptree share price target milestones ranging from $15 to $60 (adjusted for dividends paid) prior to the tenth anniversary of the date of grant, subject to the grantee’s continued employment with Tiptree.
(3)The grant date fair value of the PRSUs was estimated on the date of grant using a Black-Scholes-Merton option pricing formula embedded within a Monte Carlo model used to simulate the future stock prices of Tiptree, which assumes that the market requirement is achieved. For more detail, including the underlying valuation assumptions for PRSUs, please see Note 19, Stock Based Compensation, to our consolidated financial statements in our 2021 Annual Report on Form 10-K. Pursuant to SEC rules, the amounts shown exclude the impact of estimated forfeitures related to service-based vesting conditions.

Narrative Disclosure to Summary Compensation Table and Grants of Plan-Based Awards Table

Below is a brief description of the material terms of our NEOs’ Employment ArrangementsAgreements. There are no definite terms under the Employment Agreements, and the Company could have terminated each such NEO’s
45


employment at any time upon approval of the Board of Directors, provided that, if such NEO’s employment had been terminated without cause or he or she resigned for good reason (as defined in the Employment Agreement), then such NEO would have been entitled, subject to the execution of a general release, to certain severance payments as described in more detail below in “—Potential Payments to Named Executive Officers Upon Termination or Change in Control.” The Employment Agreements also include non-compete, non-solicitation, non-disparagement and confidentiality provisions during our NEO’s employment and for a specified period of time following the date of termination.

Michael Barnes - Executive Chairman

Under Mr. Barnes’s Executive Employment Agreement dated as of February 1, 2018, Mr. Barnes receives compensation for serving as Executive Chairman of Tiptree, consisting of an annual base salary of $600,000 and a discretionary annual cash bonus in an amount set by the CNG Committee. Effective January 1, 2022, the CNG Committee increased Mr. Barnes’s annual base salary to $1,000,000. Mr. Barnes is also eligible to participate in any stock option, restricted stock, equity compensation or other long-term incentive plan of Tiptree pursuant to the terms and conditions of such plan then in effect.

JonathanGrants of Plan-Based Awards
The following table provides additional information about non-equity and equity-based awards granted to our NEOs during the year ended December 31, 2021:
Estimated Future Payouts Under Non-Equity Incentive Plan Awards(1)
NameThresholdTargetMaximumGrant Date
Estimated Future
Payouts under
Equity Incentive
Plan Awards(2)
Grant Date Fair Value(3) ($)
Michael G. Barnes—$4,057,703—8/4/20211,500,000$4,192,400
Jonathan Ilany—$4,057,703—8/4/20211,500,000$4,192,400
Randy Maultsby———8/4/2021500,000$1,397,466
Sandra Bell—————$—
Neil C. Rifkind—————$—

(1)For Messrs. Barnes and Ilany, - Chiefthe $ figures in the table above represent the incentive compensation pool for the Executive Officer
Tiptree Asset Management Company, LLC (“TAMCO”)Committee based on a percentage of 2020 Adjusted EBITDA which was paid in the first quarter of 2021. The aggregate incentive compensation pool for our executive officers other than the Executive Committee (currently, Ms. Bell and Messrs. Maultsby and Rifkind), is subject to a subsidiarycap of 4.5% of Adjusted EBITDA prior to the payment of the incentive compensation of the Executive Committee. The actual amounts granted to Ms. Bell and Messrs. Maultsby and Rifkind were subject to the discretion of the Executive Committee and, as such, do not have calculable threshold, target or maximum estimated payouts.
(2)In 2021, the only stock awards granted were 1,500,000 PRSUs granted to each of Messrs. Barnes and Ilany and 500,000 PRSUs granted to Mr. Maultsby on August 4, 2021. A portion of the total number of PRSUs subject to the award will generally vest upon achievement of each of five Tiptree share price target milestones ranging from $15 to $60 (adjusted for dividends paid) prior to the tenth anniversary of the date of grant, subject to the grantee’s continued employment with Tiptree.
(3)The grant date fair value of the PRSUs was estimated on the date of grant using a Black-Scholes-Merton option pricing formula embedded within a Monte Carlo model used to simulate the future stock prices of Tiptree, which assumes that the market requirement is achieved. For more detail, including the underlying valuation assumptions for PRSUs, please see Note 19, Stock Based Compensation, to our consolidated financial statements in our 2021 Annual Report on Form 10-K. Pursuant to SEC rules, the amounts shown exclude the impact of estimated forfeitures related to service-based vesting conditions.

Narrative Disclosure to Summary Compensation Table and Grants of Plan-Based Awards Table

Below is a brief description of the material terms of our NEOs’ Employment Agreements. There are no definite terms under the Employment Agreements, and the Company could have terminated each such NEO’s
45


employment at any time upon approval of the Board of Directors, provided that, if such NEO’s employment had been terminated without cause or he or she resigned for good reason (as defined in the Employment Agreement), then such NEO would have been entitled, subject to the execution of a general release, to certain severance payments as described in more detail below in “—Potential Payments to Named Executive Officers Upon Termination or Change in Control.” The Employment Agreements also include non-compete, non-solicitation, non-disparagement and confidentiality provisions during our NEO’s employment and for a specified period of time following the date of termination.

Michael Barnes - Executive Chairman

Under Mr. Ilany entered into anBarnes’s Executive Employment Agreement dated as of OctoberFebruary 1, 2014 (as amended, the “Ilany Employment Agreement”). Pursuant to the Ilany Employment Agreement,2018, Mr. Ilany will receiveBarnes receives compensation for serving as Chief Executive OfficerChairman of Tiptree, and Operating Company, consisting of an initial annual base salary of $350,000$600,000 and a discretionary annual cash bonus in an amount set by the CNG Committee. Thereafter Mr. Ilany is eligible to receive an annual cash bonus in an amount determined byEffective January 1, 2022, the CNG Committee. Performance based compensation will be conditional upon, and in relationshipCommittee increased Mr. Barnes’s annual base salary to Tiptree achieving its own performance objectives with regard to growth and profitability.$1,000,000. Mr. IlanyBarnes is also eligible to participate in any stock option, restricted stock, equity compensation or other long-term incentive plan of Tiptree pursuant to the terms and conditions of such plan then in effect.
There is no definite term under the Ilany Employment Agreement, and the Company may terminate Mr. Ilany at any time upon approval of Tiptree’s board of directors. If Mr. Ilany is terminated without cause, then Mr. Ilany will be entitled, subject to the execution of a general release, to: (i) his earned but unpaid base salary, any unreimbursed business expenses and any rights or benefits to which Mr. Ilany is entitled under the terms of any employee benefit plan; (ii) earned but unpaid bonuses with respect to any performance period that ends in the calendar year prior to the calendar year in which termination occurs; and (iii) the pro rata amount up to the date of termination of bonuses and other incentive compensation that would have been payable with respect to the performance period that ends in the calendar year in which the termination occurs.
Mr. Ilany has agreed that, during his employment and for one year following the date of termination, he will not:
engage in, participate in, carry on, own, or manage, directly or indirectly, any business entity that competes or competed with the Company or any affiliate of the Company;
directly or indirectly solicit, service, or interfere with clients of, or investors in, the Company or the Company’s products or managed entities, or attempt to cause or influence any such person or entity to reduce the level of business it does with the Company; or
directly or indirectly solicit, hire, recruit, encourage, induce, or attempt to induce any employee of the Company to terminate his/her employment with the Company, or otherwise directly or indirectly employ or engage such person as an employee, independent contractor, consultant, or otherwise.
Mr. Ilany has also agreed that he will hold in confidence for the benefit of the Company, all of the information and business secrets in respect of the Company and its affiliates, and will not, at any time before or after his employment ends, willfully use, disclose or divulge any such information and that any intellectual property developed by him during his employment is, and will always remain, solely the property of the Company.



Sandra Bell - Chief Financial Officer
TAMCO and Ms. Bell entered into an Executive Employment Agreement dated as of June 12, 2015 (the “Bell Employment Agreement”). Pursuant to the Bell Employment Agreement, Ms. Bell will receive an annual base salary of $400,000 and will be eligible to receive an annual bonus. For the fiscal years 2015, 2016 and 2017, her annual bonus will be a minimum of 100% of her base salary (pro-rated for fiscal year 2015). Thereafter, Ms. Bell is eligible to receive an annual bonus in an amount determined by the CNG Committee of Tiptree’s board of directors. Any annual bonus for the fiscal years 2015 and 2016 will be paid 50% in cash and 50% in RSUs. Any annual bonus for the fiscal year 2017 and thereafter may be paid in cash and RSUs, but at least 50% in cash.
The Bell Employment Agreement provides that, on July 1, 2015 (the “Commencement Date”), Ms. Bell received grants of (i) 15,000 restricted shares of Tiptree's Class A common stock that vest at grant, but subject to forfeiture if she resigns without Good Reason (as defined in the Employment Agreement) prior to the one-year anniversary of the Commencement Date, and (ii) RSUs for a number of shares of Tiptree's Class A common stock with a value on the Commencement Date equal to $300,000, that vest equally on each of the one-year, two-year and three-year anniversaries of the Commencement Date.
There is no definite term under the Bell Employment Agreement, and the Company may terminate Ms. Bell at any time upon approval of Tiptree’s board of directors. If Ms. Bell's employment is terminated without Cause (as defined in the Bell Employment Agreement) or due to her having a disability, her death, or due to her resignation for Good Reason (as defined in the Bell Employment Agreement), then, subject to the execution of a general release, Ms. Bell will be entitled to (i) a lump sum severance payment in an amount equal to her base salary (reduced in the case of death or disability by any amounts payable under an employer sponsored plan); (ii) any earned but unpaid annual bonuses with respect to any performance period that ends in the calendar year prior to the calendar year in which termination occurs, payable solely in cash; (iii) a pro rata annual bonus with respect to the performance period that ends in the calendar year in which the termination occurs, payable solely in cash; (iv) full vesting of any then outstanding unvested equity awards; and (v) subject to her timely election of COBRA, payment of the cost of her COBRA premiums above the active employee rate through the earlier of 12 months and her becoming eligible for comparable coverage with a subsequent employer.

Ms. Bell has agreed that, during her employment and for one year following the date of termination, she will not:
engage in, participate in, carry on, own, or manage, directly or indirectly, any business entity that competes or competed with the Company or any affiliate of the Company;
directly or indirectly solicit, service, or interfere with clients of, or investors in, the Company or the Company’s products or managed entities, or attempt to cause or influence any such person or entity to reduce the level of business it does with the Company; or
directly or indirectly solicit, hire, recruit, encourage, induce, or attempt to induce any employee of the Company to terminate his/her employment with the Company, or otherwise directly or indirectly employ or engage such person as an employee, independent contractor, consultant, or otherwise.
Ms. Bell has also agreed that she will hold in confidence for the benefit of the Company, all of the information and business secrets in respect of the Company and its affiliates, and will not, at any time before or after her employment ends, willfully use, disclose or divulge any such information and that any intellectual property developed by her during her employment is, and will always remain, solely the property of the Company.

Julia Wyatt - Chief Operating Officer
TAMCO and Ms. Wyatt entered into an employment letter dated as of January 1, 2016 (the “Wyatt Employment Letter”). Pursuant to the Wyatt Employment Letter, Ms. Wyatt will receive compensation for serving as Chief Operating Officer of Tiptree, Operating Company and TFP, consisting of an initial annual base salary of $300,000 and an annual cash bonus in an amount determined by the CNG Committee.


The Wyatt Employment Letter provides that Ms. Wyatt is an employee at will and that either Tiptree or Ms. Wyatt may terminate the employment relationship at any time and for any reason, with or without cause.
Ms. Wyatt has agreed that, during her employment and for six months following the date of termination, she will not engage in, participate in, carry on, own, or manage, directly or indirectly, any business entity that competes or competed with the Company or any affiliate of the Company.
Ms. Wyatt has also agreed that, during her employment and for eighteen months following the date of termination, she will not:
directly or indirectly solicit, service, or interfere with clients of, or investors in, the Company or the Company’s products or managed entities, or attempt to cause or influence any such person or entity to reduce the level of business it does with the Company; or
directly or indirectly solicit, hire, recruit, encourage, induce, or attempt to induce any employee of the Company to terminate his/her employment with the Company, or otherwise directly or indirectly employ or engage such person as an employee, independent contractor, consultant, or otherwise.

Neil Rifkind - Vice President, General Counsel and Secretary
TAMCO and Mr. Rifkind entered into an employment letter dated as of June 17, 2013 (the “Rifkind Employment Letter”). Pursuant to the Rifkind Employment Letter, Mr. Rifkind will receive compensation for serving as Vice President, General Counsel and Secretary of Tiptree, Operating Company and TFP, consisting of an initial annual base salary of $375,000 and an annual cash bonus in an amount determined by the CNG Committee based on the recommendation of the Executive Committee’s achievement of specific annual corporate performance objectives as determined by the CNG Committee.
The Rifkind Employment Letter provides that Mr. Rifkind is an employee at will and that either Tiptree or Mr. Rifkind may terminate the employment relationship at any time and for any reason, with or without cause.
Mr. Rifkind has agreed that, during his employment and for six months following the date of termination, he will not engage in, participate in, carry on, own, or manage, directly or indirectly, any business entity that competes or competed with the Company or any affiliate of the Company.
Mr. Rifkind has also agreed that, during his employment and for eighteen months following the date of termination, he will not:
directly or indirectly solicit, service, or interfere with clients of, or investors in, the Company or the Company’s products or managed entities, or attempt to cause or influence any such person or entity to reduce the level of business it does with the Company; or
directly or indirectly solicit, hire, recruit, encourage, induce, or attempt to induce any employee of the Company to terminate his/her employment with the Company, or otherwise directly or indirectly employ or engage such person as an employee, independent contractor, consultant, or otherwise.
Other Named Executive Officers
The services of Michael G. Barnes, our Executive Chairman and for 2013, 2014 and 2015, Julia Wyatt, our Chief Operating Officer, are provided by Tricadia to the Company pursuant to the TSA described under “Certain Relationships And Related Transactions — Transactions with Related Persons — Transition Services Agreement.”
The services of Patrick Huvane, our Chief Accounting Officer, are provided to the Company by BOSG as described under “Certain Relationships and Related Transactions — Transactions with Related Persons — Transition Services Agreement.”



Grants of Plan-Based Awards

The following table provides additional information concerningabout non-equity and equity-based awards granted to our NEOs during the year ended December 31, 2021:
Estimated Future Payouts Under Non-Equity Incentive Plan Awards(1)
NameThresholdTargetMaximumGrant Date
Estimated Future
Payouts under
Equity Incentive
Plan Awards(2)
Grant Date Fair Value(3) ($)
Michael G. Barnes—$4,057,703—8/4/20211,500,000$4,192,400
Jonathan Ilany—$4,057,703—8/4/20211,500,000$4,192,400
Randy Maultsby———8/4/2021500,000$1,397,466
Sandra Bell—————$—
Neil C. Rifkind—————$—

(1)For Messrs. Barnes and Ilany, the $ figures in the table above represent the incentive compensation pool for 2015 performance. Plan-based awards that are approved by the CNGExecutive Committee atbased on a percentage of 2020 Adjusted EBITDA which was paid in the fiscal year end are issued on Januaryfirst quarter of 2021. The aggregate incentive compensation pool for our executive officers other than the Executive Committee (currently, Ms. Bell and Messrs. Maultsby and Rifkind), is subject to a cap of 4.5% of Adjusted EBITDA prior to the payment of the following year.incentive compensation of the Executive Committee. The actual amounts granted to Ms. Bell and Messrs. Maultsby and Rifkind were subject to the discretion of the Executive Committee and, as such, do not have calculable threshold, target or maximum estimated payouts.

(2)In 2021, the only stock awards granted were 1,500,000 PRSUs granted to each of Messrs. Barnes and Ilany and 500,000 PRSUs granted to Mr. Maultsby on August 4, 2021. A portion of the total number of PRSUs subject to the award will generally vest upon achievement of each of five Tiptree share price target milestones ranging from $15 to $60 (adjusted for dividends paid) prior to the tenth anniversary of the date of grant, subject to the grantee’s continued employment with Tiptree.
As disclosed(3)The grant date fair value of the PRSUs was estimated on the date of grant using a Black-Scholes-Merton option pricing formula embedded within a Monte Carlo model used to simulate the future stock prices of Tiptree, which assumes that the market requirement is achieved. For more detail, including the underlying valuation assumptions for PRSUs, please see Note 19, Stock Based Compensation, to our consolidated financial statements in greater detail elsewhere in this proxy statement, Mr. Kauffman resignedour 2021 Annual Report on November 10, 2015Form 10-K. Pursuant to SEC rules, the amounts shown exclude the impact of estimated forfeitures related to service-based vesting conditions.

Narrative Disclosure to Summary Compensation Table and Mr. Claiden resigned on February 28, 2015. Messrs. KauffmanGrants of Plan-Based Awards Table

Below is a brief description of the material terms of our NEOs’ Employment Agreements. There are no definite terms under the Employment Agreements, and Claiden were not granted any plan-based awards in 2015.

the Company could have terminated each such NEO’s
45


             
Name��Grant Date Approval Date All Other Stock Awards: Number of Shares of Stock or Units All Other Option Awards: Number of Securities Underlying Options Exercise or Base Price of Option Awards ($/Sh) 
Grant Date Fair Value(1) ($)

Michael G. Barnes(2)
 1/4/2016
 12/21/2015
 45,679
 91,359
 $5.67
 $497,843
 3/10/2016
 3/10/2016
 4,568
 9,136
 $5.87
 $51,496
Jonathan Ilany(3)
 1/4/2016
 12/21/2015
 68,519
 137,038
 $5.67
 $746,766
 3/10/2016
 3/10/2016
 6,852
 13,704
 $5.87
 $77,244
Geoffrey N. Kauffman —
 —
 —
 —
 —
 —
Sandra Bell 7/1/2015
 6/10/2015
 55,761
 —
 —
 $410,401
 1/4/2016
 12/21/2015
 15,226
 —
 —
 $86,331
Richard Claiden —
 —
 —
 —
 —
 —
Julia Wyatt 1/4/2016
 12/21/2015
 30,000
 —
 —
 $170,100
Neil C. Rifkind 1/4/2016
 12/21/2015
 22,500
 —
 —
 $127,575
Patrick Huvane 1/4/2016
 12/21/2015
 7,613
 —
 —
 $43,166

(1)See Note 21 to the Company’s Consolidated Financial Statements included in the Company’s 2015 Annual Report on Form 10-K. Stock and option award values are based on the grant date fair value computed in accordance with FASB ASC Topic 718, with the option awards computed using a Black-Scholes valuation model assuming 50% volatility. In accordance with SEC rules, estimates of forfeitures related to service-based conditions have been disregarded.
(2)As incentive compensation approved by the CNG Committee for Mr. Barnes’ services as Executive Chairman under the TSA, on January 4, 2016 and March 10, 2016, Tricadia was granted 45,679 and 4,568 Class A shares, respectively, and stock options (the “Stock Options”) to purchase 91,359 and 9,136 shares of Class A common stock of the Company, respectively, subject to the terms of a Stock Option Agreement. Exercise of the Stock Options are subject to both (1) a time-based vesting requirement with one-third vesting each of the third, fourth and fifth anniversary of the grant date of the Stock Option and (2) a performance-based vesting requirement that, at any time during the option term, the 20-day volume weighted average stock price of the Company's Class A common stock exceeds the book value per share as of December 31, 2015. The Stock Option will expire on the earlier of (1) the ten-year anniversary of the grant date of the Stock Option and (2) the date of the termination of Michael Barnes’ service with the Company for Causeemployment at any time upon approval of the Board of Directors, provided that, if such NEO’s employment had been terminated without cause or he or she resigned for good reason (as defined in the Stock Option Agreement) or Michael Barnes’ voluntary termination of service with the Company.
(3)On January 4, 2016 and March 10, 2016, Jonathan Ilany was granted 68,519 and 6,852 shares of Class A common stock, respectively, and Stock Options to purchase 137,038 and 13,704 shares of Class A common stock of the Company, respectively, subject to the terms of a Stock Option Agreement. Exercise of the Stock Options are subject to both (1) a time-based vesting requirement with one-third vesting each of the third, fourth and fifth anniversary of the grant date of the Stock Option and (2) a performance-based vesting requirement that, at any time during the option term, the 20-day volume weighted average stock price of the Company's Class A common stock exceeds the book value per share as of December 31, 2015. The Stock Option will expire on the earlier of (1) the ten-year anniversary of the grant date of the Stock Option and (2) the date of the termination of Jonathan Ilany's service with the Company for Cause (as defined in the Stock Option Agreement) or Jonathan Ilany's voluntary termination of service with the Company.





Outstanding Equity Awards
  Option Awards Stock Awards
Name 
Number of Securities Underlying Unexercised Options Exercisable

 Number of Securities Underlying Unexercised Options Unexercisable Equity Incentive Plan Awards: Number of Securities Underlying Unexercised Unearned Options Option Exercise Price ($) Option Expiration Date 
Number of
shares or units of
stock that have
not vested
(#)(1)
 
Market value of
shares of units of
stock that have
not vested
($)(2)
Michael G. Barnes —
 —
 91,359
 $5.67
 1/4/2026
 —
 —
   9,136
 $5.87
 3/10/2026
  
Jonathan Ilany —
 —
 137,038
 $5.67
 1/4/2026
 20,000
 $122,800
   13,704
 $5.87
 3/10/2026
  
Geoffrey N. Kauffman —
 —
 —
 —
 —
 —
 —
Sandra Bell —
 —
 —
 —
 —
 55,987
 $343,760
Richard Claiden —
 —
 —
 —
 —
 —
 —
Julia Wyatt —
 —
 —
 —
 —
 40,000
 $245,600
Neil C. Rifkind —
 —
 —
 —
 —
 33,500
 $205,690
Patrick Huvane —
 —
 —
 —
 —
 7,613
 $46,744
(1)The outstanding equity awards include awards that were approved by our board in December 2015 and issued on January 4, 2016 and is reduced by awards that vested on January 4, 2016.
(2)Based on the Class A common stock closing price of $6.14 on December 31, 2015.
Option Exercises and Stock Vested
  Option Awards Stock Awards
Name Number of Shares Acquired on Exercise Value Realized on Exercise ($) 
Number of Shares Acquired on Vesting(1)
 
Value Realized on Vesting ($)(2)
Michael G. Barnes —
 —
 —
 —
Jonathan Ilany —
 —
 10,000
 $56,700
Geoffrey N. Kauffman —
 —
 —
 —
Sandra Bell —
 —
 —
 —
Richard Claiden —
 —
 —
 —
Julia Wyatt —
 —
 8,733
 $49,516
Neil C. Rifkind —
 —
 5,500
 $31,185
Patrick Huvane —
 —
 —
 —
(1)The number of shares acquired on vesting consist of shares that vested in fiscal 2015 and on January 4, 2016. Ms. Wyatt acquired 1,867 shares upon vesting of RSUs on January 5, 2015 and 6,866 shares upon vesting of RSUs on January 4, 2016. Messrs. Ilany and Rifkind had RSUs vest on January 4, 2016 only.
(2)Based on the Class A common stock closing price of $5.67 on January 4, 2016.

On January 4, 2016, 32,583 shares of Class A common stock were issued to employees, including NEOs shown in the above table, upon vestingEmployment Agreement), then such NEO would have been entitled, subject to the execution of restricted stock units. The Company does not have any equity compensation programs that were not approved by stockholders.



Termination and Changea general release, to certain severance payments as described in Control Arrangements
Under the Ilany Employment Agreement and the Bell Employment Agreement, Mr. Ilany and Ms. Bell are entitledmore detail below in “—Potential Payments to payments and benefits upon the occurrence of specified events including termination of employment. The specific terms of these arrangements are discussed under the heading “Potential PaymentsNamed Executive Officers Upon Termination or Change in Control.” The Employment Agreements also include non-compete, non-solicitation, non-disparagement and confidentiality provisions during our NEO’s employment and for a specified period of time following the date of termination.

Michael Barnes - Executive Chairman

Under Mr. Barnes’s Executive Employment Agreement dated as of February 1, 2018, Mr. Barnes receives compensation for serving as Executive Chairman of Tiptree, consisting of an annual base salary of $600,000 and a discretionary annual cash bonus in an amount set by the CNG Committee. Effective January 1, 2022, the CNG Committee increased Mr. Barnes’s annual base salary to $1,000,000. Mr. Barnes is also eligible to participate in any stock option, restricted stock, equity compensation or other long-term incentive plan of Tiptree pursuant to the terms and conditions of such plan then in effect.

Jonathan Ilany - Chief Executive Officer

Under Mr. Ilany’s Executive Employment Agreement dated as of February 1, 2018, Mr. Ilany receives compensation for serving as Chief Executive Officer of Tiptree consisting of an annual base salary of $800,000 and a discretionary annual cash bonus in an amount set by the CNG Committee. Effective January 1, 2022, the CNG Committee increased Mr. Ilany’s annual base salary to $1,000,000. Mr. Ilany is also eligible to participate in any stock option, restricted stock, equity compensation or other long-term incentive plan of Tiptree pursuant to the terms and conditions of such plan then in effect.

Randy Maultsby — President

Under Mr. Maultsby’s Executive Employment Agreement dated as of July 14, 2021, Mr. Maultsby receives an annual base salary of $350,000 and a discretionary annual cash bonus in an amount set by the CNG Committee. Effective January 1, 2022, the CNG Committee increased Mr. Maultsby’s annual base salary to $500,000. Mr. Maultsby is also eligible to participate in any stock option, restricted stock, equity compensation or other long-term incentive plan of Tiptree pursuant to the terms and conditions of such plan then in effect.

Sandra Bell - Chief Financial Officer

Under Ms. Bell’s Executive Employment Agreement dated as of February 1, 2018, Ms. Bell receives a current annual base salary of $450,000 and a discretionary annual cash bonus in an amount set by the CNG Committee. Ms. Bell is also eligible to participate in any stock option, restricted stock, equity compensation or other long-term incentive plan of Tiptree pursuant to the terms and conditions of such plan then in effect.

Neil Rifkind - Vice President, General Counsel and Secretary

Under Mr. Rifkind’s Executive Employment Agreement dated as of February 1, 2018, Mr. Rifkind receives a current annual base salary of $450,000 and a discretionary annual cash bonus in an amount set by the CNG Committee. Mr. Rifkind is also eligible to participate in any stock option, restricted stock, equity compensation or other long-term incentive plan of Tiptree pursuant to the terms and conditions of such plan then in effect.


Option Exercises and Stock Vested
The following table sets forth information with respect to our NEOs regarding common stock acquired pursuant to vesting of RSUs and PRSUs in 2021. No stock options were exercised by our NEOs during 2021.
46


Stock Awards
NameNumber of Shares Acquired on Vesting
Value Realized on Vesting ($)(1)
Michael G. Barnes146,666$1,755,597
Jonathan Ilany(2)
174,666$1,901,757
Randy Maultsby66,624$677,774
Sandra Bell16,855$87,983
Neil C. Rifkind17,404$90,849


(1)    Based on the closing stock price of $5.22 on February 12, 2021, the date the RSUs vested (given that February 15, 2021 was a federal holiday, the vesting date was set at the immediately prior business day). For Messrs. Barnes, Ilany and Maultsby this also includes 100,000, 100,000 and 33,333 shares, respectively, issued on November 22, 2021 pursuant to vested PRSUs (the $15 target), with a closing stock price of $15.12.
(2)    Mr. Ilany has directed that all the shares to be issued upon vesting of his RSUs and PRSUs be issued to various family trusts. Mr. Ilany has no control over nor pecuniary interest in such family trusts.

Outstanding Equity Awards at Fiscal Year-End
The following table sets forth outstanding unexercised stock options (both exercisable and unexerciseable), unvested RSUs and unvested PRSUs held by our NEOs as of December 31, 2021. As described more fully in footnote 1 below, the stock options are subject to a time based vesting of 1/3 on each of the third, fourth and fifth anniversaries of grant and a performance based vesting requirement that has since been achieved. The remaining PRSUs will vest upon Tiptree achieving each of four remaining Tiptree share price target milestones ranging from $20 to $60 (adjusted for dividends paid) prior to the tenth anniversary of the date of grant; the $15 share price target was achieved in 2021. Any unvested PRSUs shall expire on August 4, 2031. 
Option AwardsStock Awards
NameGrant DateNumber of Securities Underlying Unexercised Options (#) Exercisable
Number of Securities Underlying Unexercised Options (#) Unexercisable(1)
Option Exercise Price(2) ($)
Option Expiration DateNumber of shares or units of stock that have not vested (#)
Market value of shares of units of stock that have not vested ($)(3)
Equity
incentive
plan awards:
Number of
unearned
shares
that have not
vested
(#)(4)
Equity
incentive
plan  awards:
Market or payout
value of
unearned
shares that
have not vested
($)(4)
Michael G. Barnes1/4/201691,359—$5.671/4/2026130,218(5)$1,800,9151,400,000 $3,679,060 
3/10/20169,136—$5.873/10/2026
2/22/2017146,31473,158$6.652/22/2027
2/26/201831,11062,222$5.852/26/2028
2/26/2019—90,326$6.262/26/2029
2/20/2020—170,111$7.252/20/2030
Jonathan Ilany1/4/2016137,038—$5.671/4/2026195,327(6)$2,701,3721,400,000 $3,679,060 
3/10/201613,704—$5.873/10/2026
2/22/2017234,103117,052$6.652/22/2027
2/26/201849,77799,554$5.852/26/2028
2/26/2019—135,489$6.262/26/2029
2/20/2020—255,166$7.252/20/2030
Randy Maultsby————30,966(7)$428,260466,667 $1,226,354 
Sandra Bell————16,212(8)$224,212— $— 
Neil C. Rifkind————16,476(9)$227,863— $— 


47


(1)All outstanding and unexercised stock options have met their performance-based vesting requirements and remain subject to the time-based vesting requirements before becoming exercisable. For Mr. Barnes, the unexercised, unearned options consist of (a) 73,158 Stock Options granted on February 22, 2017 which will become exercisable on February 22, 2022, (b) 62,222 Stock Options granted on February 26, 2018 which will become exercisable in equal installments on each of February 26, 2022 and 2023, (c) 90,326 Stock Options granted on February 26, 2019 which will become exercisable in equal installments on each of February 26, 2022, 2023 and 2024 and (d) 170,111 Stock Options granted on February 20, 2020 which will become exercisable in equal installments on each of February 26, 2023, 2024 and 2025. For Mr. Ilany, the unexercised, unearned options consist of (a) 117,052 Stock Options granted on February 22, 2017 which will become exercisable on February 22, 2022, (b) 99,554 Stock Options granted on February 26, 2018 which will become exercisable in equal installments on each of February 26, 2022 and 2023, (c) 135,489 Stock Options granted on February 26, 2019 which will become exercisable in equal installments on each of February 26, 2022, 2023 and 2024 and (d) 255,166 Stock Options granted on February 20, 2020 which will become exercisable in equal installments on each of February 26, 2023, 2024 and 2025. The Stock Options will expire on the earlier of (1) the ten-year anniversary of the grant date of the Stock Option and (2) the date of the termination of Mr. Barnes’s (with respect to Mr. Barnes’s Stock Options) or Mr. Ilany’s (with respect to Mr. Ilany’s Stock Option) service with the Company for cause (as defined in the Stock Option Agreement) or their respective voluntary termination of service with the Company (other than a termination of employment for good reason (as defined in the Employment Agreement) or for retirement (as defined below under “—Potential Payments to Named Executive Officers Upon Termination or Change in Control”).
(2)Based on the common stock closing price on the date such options are granted.
(3)Based on the common stock closing price of $13.83 on December 31, 2021.
(4)Consists of PRSUs that vest upon Tiptree satisfying the relevant Tiptree share price target milestones in accordance with the terms of these arrangements were negotiated as a partthe PRSUs. The fair value of the PRSUs are estimated on the date of grant using a Black-Scholes-Merton option pricing formula embedded within a Monte Carlo model used to simulate the future stock prices of Tiptree, which assumes that the market requirement is achieved. For more detail, including the underlying valuation assumptions for PRSUs and stock option awards, please see Note 19, Stock Based Compensation, to our consolidated financial statements in our 2021 Annual Report on Form 10-K.
(5)Consists of the 45,163 RSUs and 85,055 RSUs that are subject to cliff vesting on February 15, 2022 and 2023, respectively, based upon his continuous employment from the grant date until such date, subject to certain terms contained in his RSU award agreement.
(6)Consists of the 67,744 RSUs and 127,583 RSUs that are subject to cliff vesting on February 15, 2022 and 2023, respectively, based upon continuous employment of Mr. Ilany Employment Agreementfrom the grant date until such date, subject to certain terms contained in his RSU award agreement. Mr. Ilany has directed that all the shares to be issued upon vesting of his PRSUs and RSUs be issued to various family trusts. Mr. Ilany has no control over nor pecuniary interest in such family trusts.
(7)Consists of the remaining 20,411 RSUs granted to him on February 20, 2020, which will vest annually in two equal installments on each of February 15, 2022 and 2023 and the remaining 10,555 RSUs granted to him on February 26, 2019, which will vest on February 15, 2022, in each case generally subject to Mr. Maultsby’s continuous employment from the grant date until such vesting date and the terms contained in Mr. Maultsby’s award agreements.
(8)Ms. Bell’s 16,212 unvested RSUs consist of (a) the remaining 10,670 RSUs granted to her on February 20, 2020, which will vest in two equal installments on each of February 15, 2022 and 2023 and (b) the remaining 5,542 RSUs granted to her on February 26, 2019, which will vest on February 15, 2022, in each case generally subject to Ms. Bell’s continuous employment from the grant date until such vesting date and the terms contained in Ms. Bell’s award agreements.
(9)Mr. Rifkind’s 16,476 unvested RSUs consist of (a) the remaining 10,670 RSUs granted to him on February 20, 2020, which will vest in two equal installments on each of February 15, 2022 and 2023 and (b) the remaining 5,806 RSUs granted to him on February 26, 2019, which will vest on February 15, 2022, in each case generally subject to Mr. Rifkind’s continuous employment from the grant date until such vesting date and the terms contained in Mr. Rifkind’s award agreements.

Potential Payments to Named Executive Officers Upon Termination or Change in Control
The Employment Agreements provide for severance payments if the employment of an NEO is terminated by the Company without “cause” (as defined in the Employment Agreement) or due to disability or death, or by such NEO for “good reason” (as defined in the Employment Agreement). Upon such a termination, then, subject to the execution of a general release, each NEO will be entitled to receive (i) a lump sum severance payment in an amount equal to (A) in the case of Messrs. Barnes and Ilany, (I) two times base salary and (II) the average of the annual bonuses paid to the executive with respect to the two calendar years immediately preceding the year that termination occurs, multiplied by one plus a fraction, the numerator of which is the number of full months of employment the executive completed in the year in which termination occurs and the denominator of which is twelve and (B), in the case of Ms. Bell Employment Agreement and were considered reasonableMessrs. Maultsby and Rifkind, one times base salary and the prior year's annual bonus, provided that in lightthe case of a termination of employment due to an executive’s death or disability, any severance pay will be reduced by amounts payable to an executive, or his or her estate, under an employer sponsored plan; (ii) any earned but unpaid annual bonus with respect to any performance period that ends in the calendar year prior to the calendar year in which termination occurs, payable solely in cash; (iii) full vesting with respect to the time-based vesting condition (immediately in the case of death, disability, termination without cause or termination for good reason) of any then outstanding unvested equity awards and awards subject to performance-based vesting conditions remain outstanding for their term and eligible to vest on achievement of the performance requirement; and (iv) payment of the cost of COBRA premiums above the active employee rate through the earlier of 18 months following termination and the date the executive becomes eligible for comparable coverage with a subsequent employer.
48

We do not have severance arrangements with our NEOs in connection with a change of control. However, upon the occurrence of a change of control, RSU awards granted to the NEOs are accelerated and the time-vesting requirement of the stock options granted to our NEOs is waived (since the stock options have all met their performance requirement, upon a chance of control, they will all become immediately exercisable).
As used in our award agreements, the term “retirement” means the participant is at least 55 years old and satisfies the “Rule of 65” which means that the sum of the Participant’s age and years of combined and continuous service with the Company equals at least sixty-five (65). For purposes of determining the Rule of 65, only full years of service with the Company shall count as years of combined and continuous service. Currently, of our intention to recruitNEOs, only Mr. Ilany and Ms. Bell qualify for retirement.
Michael Barnes
•If Mr. Barnes’s employment was terminated by the Company without cause or due to join our Company.his death or disability (or he terminated employment for good reason) as of December 31, 2021, he would have been entitled to receive a total severance of $5,557,703, which represents two times his base salary and the average of his annual cash bonus for the past two calendar years multiplied by two and his 130,218 unvested RSUs as of December 31, 2021 would vest immediately.
•Upon a change of control, Mr. Barnes’s unvested RSUs become fully vested. His 130,218 unvested RSUs as of December 31, 2021, with an aggregate market value of $1,800,915 based on the Company’s closing stock price of $13.83 as of December 31, 2021 would become fully vested.
•If Mr. Barnes’s employment was terminated by the Company without cause or due to his death, disability or upon a change of control of the Company, all of Mr. Barnes’s stock options will be exercisable, given their performance requirements have been achieved.
•With respect to Mr. Barnes’s 1,400,000 unvested PRSUs as of December 31, 2021:
◦If Mr. Barnes’s employment was terminated by the Company without cause, or due to his death or disability, or as a result of his retirement after August 4, 2024, then such unvested PRSUs shall remain outstanding and be eligible to vest upon Tiptree satisfying the relevant Tiptree share price target milestones in accordance with the terms of the PRSUs.
◦Upon a change of control, only those PRSUs that satisfy the relevant Tiptree share price target milestones from such a change of control transaction will vest, with all other PRSUs becoming forfeited unless otherwise assumed in such a change of control transaction.
Jonathan Ilany
•If Mr. Ilany’s employment was terminated by the Company without cause or due to his death or disability (or he terminated employment for good reason) as of December 31, 2021, he would have been entitled to receive a total severance of $5,957,703, which represents two times his base salary and the average of his annual cash bonus for the past two calendar years multiplied by two and his 195,327 unvested RSUs as of December 31, 2021 would vest immediately; his unvested RSUs would remain outstanding and vest in accordance with their vesting schedule in the case of Mr. Ilany’s retirement.
•Upon a change of control, Mr. Ilany’s 195,327 unvested RSUs as of December 31, 2021, with a market value of $2,701,372 based on the Company’s closing stock price of $13.83 as of December 31, 2021, would also become fully vested.
•If Mr. Ilany’s employment was terminated by the Company without cause or due to his death, disability or retirement, or upon a change of control of the Company, all of Mr. Ilany’s stock options will be exercisable, given their performance requirements have been achieved.
•With respect to Mr. Ilany’s 1,400,000 unvested PRSUs as of December 31, 2021:
49

◦If Mr. Ilany’s employment was terminated by the Company without cause, or due to his death or disability, or as a result of his retirement after August 4, 2024, then such unvested PRSUs shall remain outstanding and be eligible to vest upon Tiptree satisfying the relevant Tiptree share price target milestones in accordance with the terms of the PRSUs.
◦Upon a change of control, only those PRSUs that satisfy the relevant Tiptree share price target milestones from such a change of control transaction will vest, with all other PRSUs becoming forfeited unless otherwise assumed in such a change of control transaction.
Randy Maultsby
•If Mr. Maultsby’s employment was terminated by the Company without cause or due to his death or disability (or he terminated employment for good reason) as of December 31, 2021, he would have been entitled to receive a total severance of $1,600,000, which represents his base salary and incentive compensation for services performed in 2021 and his 30,966 unvested RSUs as of December 31, 2021 would vest immediately.
•Upon a change of control, Mr. Maultsby’s 30,966 unvested RSUs as of December 31, 2021, with a market value of $428,260 based on the Company’s closing stock price of $13.83 as of December 31, 2021, would become fully vested.
•With respect to Maultsby’s 466,667 unvested PRSUs as of December 31, 2021:
◦If Mr. Maultsby’s employment was terminated by the Company without cause, or due to his death or disability, or as a result of his retirement after August 4, 2024, then such unvested PRSUs shall remain outstanding and be eligible to vest upon Tiptree satisfying the relevant Tiptree share price target milestones in accordance with the terms of the PRSUs.
◦Upon a change of control, only those PRSUs that satisfy the relevant Tiptree share price target milestones from such a change of control transaction will vest, with all other PRSUs becoming forfeited unless otherwise assumed in such a change of control transaction.
Sandra Bell
•If Ms. Bell’s employment was terminated by the Company without cause or due to her death or disability (or she terminated employment for good reason) as of December 31, 2021, she would have been entitled to receive a total severance of $1,300,000, which represents her base salary and incentive compensation for services performed in 2021 and her 16,212 unvested RSUs as of December 31, 2021 would vest immediately; her unvested RSUs would remain outstanding and vest in accordance with their vesting schedule in the case of Ms. Bell’s retirement.
•Upon a change of control, Ms. Bell’s 16,212 unvested RSUs as of December 31, 2021, with a market value of $224,212 based on the Company’s closing stock price of $13.83 as of December 31, 2021, would become fully vested.
Neil Rifkind
•If Mr. Rifkind’s employment was terminated by the Company without cause or due to his death or disability (or he terminated employment for good reason) as of December 31, 2021, he would have been entitled to receive a total severance of $1,300,000, which represents his base salary and incentive compensation for services performed in 2021 and his 16,476 unvested RSUs as of December 31, 2021 would remain outstanding and vest immediately.
•Upon a change of control, Mr. Rifkind’s 16,476 unvested RSUs as of December 31, 2021, with a market value of $227,863 based on the Company’s closing stock price of $13.83 as of December 31, 2021, would become fully vested.
50


Equity Compensation
The CNG Committee, may, from time to time, grant equity awards pursuant to our equity plans that are designed to align the interests of our executive officers with those of our stockholders, by allowing our executive officers to share in the creation of value for our stockholders through stock appreciation and dividends. The equity awards granted to our executive officers are designed to promote the retention of management and to achieve strong performance for our Company. These awards further provide flexibility to us in our ability to attract, motivate and retain talented individuals.
Potential Payments to Named Executive Officers Upon Termination or Change in Control
Mr. Ilany, Ms. Bell and Mr. Rifkind are the only NEOs with an employment contract. Ms. Wyatt entered into an employment contract on January 1, 2016 and Mr. Schott on March 10, 2016.
If Mr. Ilany is terminated without cause, then Mr. Ilany will be entitled, subject to the execution of a general release, to (i) his earned but unpaid base salary, any unreimbursed business expenses and any rights or benefits to which Mr. Ilany is entitled under the terms of any employee benefit plan; (ii) earned but unpaid bonuses with respect to any performance period that ends in the calendar year prior to the calendar year in which termination occurs; and (iii) the pro rata amount up to the date of termination of bonuses and other incentive compensation that would have been payable with respect to the performance period that ends in the calendar year in which the termination occurs.
If Ms. Bell is terminated without cause or due to her disability, death, or resignation for Good Reason (as defined in the Bell Employment Agreement), then, subject to the execution of a general release, Ms. Bell will be entitled to (i) a lump sum severance payment in an amount equal to her base salary (reduced in the case of death or disability by any amounts payable under an employer sponsored plan); (ii) any earned but unpaid annual bonuses with respect to any performance period that ends in the calendar year prior to the calendar year in which termination occurs, payable solely in cash; (iii) a pro rata annual bonus with respect to the performance period that ends in the calendar year in which the termination occurs, payable solely in cash; (iv) full vesting of any then outstanding unvested equity awards; and (v) subject to her timely election of COBRA, payment of the cost of her COBRA premiums above the active employee rate through the earlier of 12 months and her becoming eligible for comparable coverage with a subsequent employer.
If Mr. Rifkind is terminated for any reason, he is entitled to his salary until the date of termination.
Equity Compensation Plans

Set forth below is certain information, as of December 31, 2015,2021, regarding equity compensation granted in 2021 that has been approved by stockholders:stockholders. For additional information, please see Note 19—Stock Based Compensation, to the consolidated financial statements contained in Tiptree’s 2021 10-K.
Equity compensation plans approved by stockholdersNumber of securities to be issued upon exercise of outstanding options, warrants and rightsWeighted average exercise priceNumber of securities remaining available for issuance under plan
2017 equity plan1,715,619(a)$6.49(b)2,344,814 

(a)    Consists of the common stock that may be issued upon outstanding stock options that became exercisable as of December 31, 2021, based on the Company meeting performance metrics pursuant to the terms of such stock options. The Company did not grant any stock options or RSUs were in 2021. This does not include the 3,500,000 PRSUs granted in 2021 of which 3,266,667 remain unvested. This also does not include 1,423,604 shares of our common stock that may be issued pursuant to outstanding unvested subsidiary RSUs.

(b)    This weighted-average exercise price relates only to the stock options described in footnote (a).

51


Equity compensation plans approved by stockholdersNumber of securities to be issued upon exercise of outstanding options, warrants and rightsWeighted average exercise priceNumber of securities remaining available for issuance under plan
Manager plan(1)
—N/A134,629
2013 equity plan—N/A1,582,339
SECURITY OWNERSHIP OF CERTAIN BENEFICIAL OWNERS AND MANAGEMENT
(1) No shares have been issued since March 30, 2012 from this plan and no future issuances are expected from this plan.



SECURITY OWNERSHIP OF CERTAIN BENEFICIAL OWNERS AND MANAGEMENT
Beneficial Owners of More Than 5% of Common Stock and Directors and Named Executive Officers
The following table sets forth the beneficial ownership of our Class A common stock, as of March 31, 2016,April 14, 2022, for: (1) each person known to us to be the beneficial owner of more than 5% of our Class A outstanding common stock; (2) each of our directors and nominees for director; (3) each of our NEOs; and (4) our directors, nominees for director and current executive officers as a group. Except as otherwise described in the notes below, the following beneficial owners have sole voting power and sole investment power with respect to all shares of common stock set forth opposite their respective names.
The percentage ownership data is based on 34,914,772 shares of our Class A common stock issued and outstanding as of March 31, 2016. We also have issued and outstanding 8,049,029 shares of Class B common stock that generally vote together on all matters with the Class A common stock. All of the Class B common stock is owned by TFP. Pursuant to the limited liability company operating agreement of the Operating Company, from and after July 1, 2014, on a monthly basis, TFP’s limited partners other than Tiptree may directly exchange TFP partnership units for Class A common stock of Tiptree (at a rate of 2.798 shares of Class A common stock per TFP partnership unit, subject to certain conditions and limitations). An equal number of Class B shares are canceled when Class A shares are issued in exchanges, with the result that the total number of shares entitled to vote is not affected by exchanges. As of March 31, 2016, TFP owns 100% of Operating Company and Tiptree owns approximately 81% of TFP. The percentage of TFP (and therefore Operating Company) owned by Tiptree may increase in the future to the extent TFP limited partners exchange their limited partnership units of TFP for Class A common stock of Tiptree.
If all of the limited partners of TFP were to elect to redeem their partnership units for Class A common stock, an additional 8,049,029 shares of our Class A common stock would be issuable (excluding 3,767,034 shares of Class A common stock issuable upon redemption of Operating Company units issuable upon exercise of warrants and options to acquire partnership units). In addition, TFP owns a warrant to acquire 652,500 shares of Class A common stock at $11.33 per share. For the officers, directors and affiliates, we have included information regarding Class A common stock issuable upon redemption of Operating Company units as beneficially owned.
In accordance with SEC rules, each listed person’s beneficial ownership includes:

•all shares the investor actually owns beneficially or of record;
•all shares over which the investor has or shares voting or dispositive control (such as in the capacity as a general partner of an investment fund); and
•all shares the investor has the right to acquire within 60 days (such as upon exercise of options that are currently vested or which are scheduled to vest within 60 days).

Unless otherwise indicated, all shares are owned directly and the indicated person has sole voting and investment power. Unless otherwise indicated, the business address for each beneficial owner listed below is c/o Tiptree Financial Inc., 780 Third299 Park Avenue, 21st13th Floor, New York, New York 10017.10171.
There can be no assurance that the persons listed below will choose to redeem TFP units for shares of Class A Common stock in the table below.



Name Number of Shares of
Class A Common Stock Beneficially Owned		 Percent of Class A
Common Stock
Greater than 5% Stockholders    
Michael G. Barnes(1)
 12,476,649 28.43%
Tiptree Financial Partners L.P.(2)
 12,468,563 26.31%
Arif Inayatullah(3)
 9,601,612 21.90%
The Goldman Sachs Group, Inc.(4)
 5,632,018 16.13%
TFPLP Holdings I LLC(5)
 4,865,529 12.23%
Nomura Securities Co., Ltd(6)
 3,622,717 10.38%
Canyon Value Realization Fund, L.P.(7)
 2,708,344 7.76%
Bank of America Corporation(8)
 2,411,425 6.91%
TFPLP Holdings III LLC(9)
 1,942,590 5.56%
     
Directors    
Michael G. Barnes(1)
 12,476,649 28.43%
Lesley Goldwasser 5,145 *
William A. Houlihan** 18,659 *
Jonathan Ilany(10)
 17,863 *
Geoffrey N. Kauffman** 672,221 1.93%
John E. Mack 3,250 *
Richard A. Price 14,486 *
Bradley E. Smith(11)
 82,540 *
     
Executive Officers    
Michael G. Barnes(1)
 12,476,649 28.43%
Sandra Bell(12)
 15,000 *
Richard Claiden** — *
Patrick Huvane(13)
 16,588 *
Jonathan Ilany(10)
 17,863 *
Geoffrey N. Kauffman** 672,221 1.93%
Neil C. Rifkind(14)
 7,505 *
Timothy Schott(15)
 — *
Julia Wyatt(16)
 84,168 *
All Current Directors and Executive Officers as a Group (11 Persons) ** 12,723,194 28.99%
NameNumber of Shares of
Common Stock Beneficially Owned		Percent of Common Stock
Greater than 5% Stockholders
Michael G. Barnes(1)
9,796,13027.18%
Arif Inayatullah(2)
3,535,71810.01%
Dimensional Fund Advisors LP(3)
2,636,6527.56%
Directors, Director Nominees, and Officers
Michael G. Barnes(1)
9,796,13027.18%
Paul M. Friedman92,596*
Lesley Goldwasser83,232*
Jonathan Ilany(4)
845,2322.38%
Dominique Mielle50,883*
Bradley E. Smith(5)
156,816*
Randy Maultsby(6)
58,154*
Sandra Bell(7)
27,762*
Neil C. Rifkind(8)
37,180*
All Directors and Executive Officers as a Group (9 Persons)11,196,53331.06%
*The percentage of shares beneficially owned does not exceed one percent of the total shares of our Class A common stock outstanding.
**As disclosed in greater detail herein, Messrs. Houlihan, Kauffman and Claiden's tenure with the Company ceased in 2015. Their respective share ownership amounts are based on their ownership as of the last date of their tenure with the Company.

(1)Mr. Barnes is deemed to beneficially own 12,476,649 shares of Class A common stock consisting of 3,505,110 shares of Class A common stock over which Mr. Barnes has sole voting and dispositive power, 652,500 shares of Class A common stock issuable pursuant to a warrant owned by TFP over which Mr. Barnes has shared voting and dispositive power, 50,247 shares of Class A common stock held by Tricadia Holdings, L.P. over which Mr. Barnes has shared voting and dispositive power, 4,907,343 shares of Class A common stock issuable in redemption of TFP partnership units owned by TFPLP Holdings I LLC (“TFPLP I”) and TFPLP Holdings III LLC (“TFPLP III”) over which Mr. Barnes has shared voting and dispositive power and 3,411,696 shares of Class A common stock issuable upon exercise of warrants owned by TFPLP I and TFPLP III over which Mr. Barnes has shared voting and dispositive control. Mr. Barnes disclaims beneficial ownership of these securities except to the extent of his pecuniary interest.
(2)
The shares issuable upon redemption consists of 8,049,029 shares of Class A common stock issuable upon redemption by TFP of membership units of Operating Company owned by it and 4,419,534 shares of Class A common stock issuable upon exercise of warrants held by TFP.
(3)Mr. Inayatullah is deemed to beneficially own 9,601,612 shares of Class A common stock consisting of 615,031 shares of Class A common stock over which Mr. Inayatullah has sole voting and dispositive power, 617,295 shares of Class A common stock issuable in redemption of TFP partnership units over which Mr. Inayatullah has sole voting and dispositive control, 50,247 shares of Class A common stock held by


Tricadia Holdings, L.P. over which Mr. Inayatullah has shared voting and dispositive power, 4,907,343Barnes is deemed to beneficially own 9,796,130 shares of Class A common stock issuable in redemptionconsisting of TFP partnership units owned by TFPLP I and TFPLP III over which Mr. Inayatullah has shared voting and dispositive control and 3,411,6968,637,894 shares of Class Acommon stock Mr. Barnes owns directly and 1,158,236 shares of common stock issuable upon exercise of warrants and vested stock options that Mr. Barnes owns directly. Excludes the remaining 1,400,000 PRSUs granted on August 4, 2021 subject to vesting upon Tiptree achieving each of four Tiptree share price target milestones, based on the average of the thirty (30) trading day closing stock price, ranging from $20 to $60 (adjusted for dividends paid) prior to the tenth anniversary of the date of grant, subject to Mr. Barnes’s continued employment with Tiptree. Any unvested PRSUs shall expire on August 4, 2031.
52

(2)Mr. Inayatullah is deemed to beneficially own 3,535,718 shares of common stock consisting of 3,097,094 shares of common stock Mr. Inayatullah owns directly and 438,624 shares of common stock issuable upon exercise of warrants and stock options that Mr. Inayatullah owns directly.
(3)Based on the Schedule 13G filed on February 8, 2022, based on common stock held on December 31, 2021. The mailing address for this reporting person is 6300 Bee Cave Road, Austin, Texas, 78746.
(4)Mr. Ilany is deemed to beneficially own 845,232 shares of common stock consisting of 198,618 shares of common stock Mr. Ilany owns directly and 646,614 shares of common stock issuable upon exercise of vested stock options that Mr. Ilany owns directly. Excludes an aggregate of 1,243,227 shares of common stock held at various estate planning vehicles for the benefit of Mr. Ilany’s family. Mr. Ilany has no control over nor pecuniary interest in any of these estate planning vehicles. Also excludes the remaining 1,400,000 PRSUs granted on August 4, 2021 subject to vesting upon Tiptree achieving each of four Tiptree share price target milestones, based on the average of the thirty (30) trading day closing stock price, ranging from $20 to $60 (adjusted for dividends paid) prior to the tenth anniversary of the date of grant, subject to Mr. Ilany’s continued employment with Tiptree. Any unvested PRSUs shall expire on August 4, 2031.
(5)Includes 63,738 shares of common stock owned by TFPLP IKahala Capital Advisors LLC (“Kahala”). Mr. Smith is a principal of Kahala.
(6)Excludes (a) the remaining 10,206 RSUs, which were granted to Mr. Maultsby on February 20, 2020 and TFPLP III over which Mr. Inayatullah has shared votingwill vest on February 15, 2023 and dispositive control. Mr. Inayatullah disclaims beneficial ownership(b) the remaining 466,667 PRSUs granted on August 4, 2021 subject to vesting upon Tiptree achieving each of these securities exceptfour Tiptree share price target milestones, based on the average of the thirty (30) trading day closing stock price, ranging from $20 to $60 (adjusted for dividends paid) prior to the extenttenth anniversary of his pecuniary interest.the date of grant, subject to Mr. Maultsby’s continued employment with Tiptree. Any unvested PRSUs shall expire on August 4, 2031.
(7)Excludes (a) the remaining 5,335 RSUs, which were granted to Ms. Bell on February 20, 2020 and will vest on February 15, 2023 and (b) the 26,750 RSUs, which were granted on February 17, 2022 and will cliff vest on February 20, 2025, all of which are subject to Ms. Bell’s continuous employment from the grant date until such date and subject to certain terms contained in Ms. Bell’s award agreements.
(8)Excludes (a) the remaining 5,335 RSUs, which were granted to Mr. Rifkind on February 20, 2020 and will vest on February 15, 2023 and (b) the 26,750 RSUs, which were granted on February 17, 2022 and will cliff vest on February 20, 2025, all of which are subject to Mr. Rifkind’s continuous employment from the grant date until such date and subject to certain terms contained in Mr. Rifkind’s award agreements.

53



(4)Based on the Schedule 13G filed on February 12, 2016, based on Class A common stock held on December 31, 2015 by The Goldman Sachs Group, Inc., Goldman, Sachs & Co., GS Advisors VI, L.L.C., GSCP VI Advisors, L.L.C., GSCP VI Offshore Advisors, L.L.C., Goldman, Sachs Management GP GMBH, GS Capital Partners VI Fund, L.P., GS Capital Partners VI Offshore Fund, L.P., GS Capital Partners VI GmbH & Co. KG, GS Capital Partners VI Parallel, L.P., GSCP VI Parallel ProSight, L.L.C., ProSight Equity Management Inc., ProSight Investment LLC and ProSight Parallel Investment LLC. The mailing address of this reporting person is 200 West Street New York, NY 10282.CERTAIN RELATIONSHIPS AND RELATED TRANSACTIONS
(5)Consists of 3,569,509 shares of Class A common stock issuable in redemption of TFP partnership units owned by TFPLP I and 1,296,020 shares of Class A common stock issuable in redemption upon exercise of warrants to acquire TFP partnership units owned by TFPLP I. Mr. Barnes and Mr. Inayatullah have shared voting and dispositive control over the securities beneficially owned by TFPLP I.
(6)Based on the Schedule 13G filed on February 16, 2016. The mailing address of this reporting person is 1-9-1 Nihonbashi Chuo-ku, Tokyo 103-8645, Japan.
(7)Based on the Schedule 13G filed on February 12, 2016, based on Class A common stock held on December 31, 2015. The mailing address for this reporting person is 2000 Avenue of the Stars, 11th Floor, Los Angeles, CA 90067.
(8)Based on the Schedule 13G filed on February 16, 2016, by Bank of America Corporation on behalf of itself and its wholly owned subsidiaries, Merrill Lynch Pierce Finner & Smith, Inc., Bank of America N.A. and Blue Ridge Investments, LLC, based on Class A common stock held on December 31, 2015. The mailing address of this reporting person is Bank of America Corporate Center, 100 N. Tryon Street, Charlotte, NC 28255.
(9)Consists of 1,337,834 shares of Class A common stock issuable in redemption of TFP partnership units owned by TFPLP III and 604,756 shares of Class A common stock issuable in redemption upon exercise of warrants to acquire TFP partnership units. Mr. Barnes and Mr. Inayatullah have shared voting and dispositive control over the securities beneficially owned by TFPLP III.
(10)Excludes 98,764 shares of Class A common stock held at the Ilany Family Exempt Trust. Also excludes the remaining 20,000 RSUs, which were granted to Mr. Ilany on January 5, 2015 and represent the right to receive shares of Class A common stock pursuant to the Company’s equity plan. The RSUs will vest annually in two remaining equal installments on each of January 3, 2017 and January 3, 2018 upon continuous employment from the grant date until such date, subject to certain terms contained in Mr. Ilany’s award agreement. Mr. Ilany has directed that the shares to be issued upon vesting of such RSUs be issued to the Ilany Family Exempt Trust. Also excludes 85,371 shares of Class A common stock issuable to Mr. Ilany as stock based compensation in 2015 which Mr. Ilany has directed be issued to the Ilany Family Exempt Trust. Mr. Ilany has no control over nor pecuniary interest in the Ilany Family Exempt Trust.
(11)Includes 63,738 shares of Class A common stock owned by Kahala Capital Advisors LLC (“Kahala”). Mr. Smith is a principal of Kahala and disclaims beneficial ownership of the securities owned by Kahala except to the extent of his pecuniary interest.
(12)Excludes 55,987 RSUs, which were granted to Ms. Bell, 15,226 of which were granted on January 4, 2016 (the “Bell 2016 RSUs”) and represent the right to receive shares of Class A common stock pursuant to the Company’s equity plan and 40,761 of which were granted on July 1, 2015 (the “Bell 2015 RSUs”). The Bell 2016 RSUs will vest annually in three equal installments on each of January 4, 2017, January 4, 2018 and January 4, 2019 upon continuous employment from the grant date until such date, subject to certain terms contained in Ms. Bell’s award agreement. The Bell 2015 RSUs will vest annually in three equal installments on each of July 1, 2016, July 1, 2017 and July 1, 2018 upon continuous employment from the grant date until such date, subject to certain terms contained in Ms. Bell’s award agreement.
(13)Excludes 7,613 RSUs, which were granted to Mr. Huvane on January 4, 2016 and represent the right to receive shares of Class A common stock pursuant to the Company’s equity plan. The RSUs will vest annually in three equal installments on each of January 4, 2017, January 4, 2018 and January 4, 2019 upon continuous employment from the grant date until such date, subject to certain terms contained in Mr. Huvane’s award agreement.
(14)Excludes 22,500 RSUs, which were granted to Mr. Rifkind on January 4, 2016 and represent the right to receive shares of Class A common stock pursuant to the Company’s equity plan. The RSUs will vest annually in three equal installments on each of January 4, 2017, January 4, 2018 and January 4, 2019 upon continuous employment from the grant date until such date, subject to certain terms contained in Mr. Rifkind’s award agreement. Also excludes the remaining 11,000 RSUs, which were granted to Mr. Rifkind on January 5, 2015 (the “Rifkind 2015 RSUs”) and represent the right to receive shares of Class A common stock pursuant to the Company’s equity plan. The Rifkind 2015 RSUs will vest annually in two remaining equal installments on each of January 3, 2017 and January 3, 2018 upon continuous employment from the grant date until such date, subject to certain terms contained in Mr. Rifkind’s award agreement.
(15)Mr. Schott was appointed our Principal Accounting Officer on March 10, 2016.
(16)Excludes 30,000 RSUs, which were granted to Ms. Wyatt on January 4, 2016 and represent the right to receive shares of Class A common stock pursuant to the Company’s equity plan. The RSUs will vest annually in three equal installments on each of January 4, 2017, January 4, 2018 and January 4, 2019 upon continuous employment from the grant date until such date, subject to certain terms contained in Ms. Wyatt’s award agreement. Also excludes the remaining 10,000 RSUs, which were granted to Ms. Wyatt on January 5, 2015 (the “Wyatt 2015 RSUs”) and represent the right to receive shares of Class A common stock pursuant to the Company’s equity plan. The Wyatt 2015 RSUs will vest annually in two remaining equal installments on each of January 3, 2017 and January 3, 2018 upon continuous employment from the grant date until such date, subject to certain terms contained in Ms. Wyatt’s award agreement.
Section 16(a) Beneficial Ownership Reporting Compliance
Section 16(a) of the Exchange Act requires our executive officers and directors, and persons who own more than 10% of a registered class of our equity securities, to file reports of ownership and changes in ownership with the SEC. Officers, directors and persons who own more than 10% of a registered class of our equity securities are required to furnish us with copies of all Section 16(a) forms that they file. To our knowledge, based solely on review of the copies of such reports furnished to us, all Section 16(a) filing requirements applicable to our executive officers, directors and persons who own more than 10% of a registered class of our equity securities were filed on a timely basis except that Mr. Barnes filed a Form 4 one day late with respect to his purchase of Tiptree shares in the open market on April 28, 2015, pursuant to a Rule 10b5-1 trading plan.


CERTAIN RELATIONSHIPS AND RELATED TRANSACTIONS
Policies and Procedures with Respect to Related Party Transactions
Pursuant to the Related Person Transaction Policy set forth in the Charter of the Audit Committee of the Board of Directors, the “Related Person Transaction Policy” requires that all related party transactions (generally, transactions involving amounts exceeding $120,000 in which a related party (directors, director nominees and executive officers or their immediate family members, or stockholders owning 5% or more of our outstanding stock) had or will have a direct or indirect material interest) shall be subject to pre-approval or ratification by the Audit Committee in accordance with the following procedures. No related party transaction shall be approved or ratified if such transaction is contrary to our best interests.
Each party to a potential related party transaction is responsible for notifying our Chief Compliance Officer (or such other person as the Audit Committee may require) of the potential related person transaction in which such person or any immediate family member of such person may be directly or indirectly involved as soon as he or she becomes aware of such transaction. Except in circumstances where such transaction is expected to qualify as an ordinary course transaction (generally: (i) transactions that occur between the Company or any of its subsidiaries and an entity for which any related person serves as an executive officer, partner, principal, member or any similar executive or governing capacity; (ii) an ordinary course transaction in which such related person has an economic interest that does not afford such related person control over such entity on terms and conditions no less favorable to the Company; or (iii) immaterial relationships and transactions in the Instructions to Item 404(a) of Regulation S-K of the Securities Act), such notification should be made prior to the time that the transaction is entered into and such notice shall provide the Chief Compliance Officer (or such other person) a reasonable opportunity, under the circumstances, for the required review of such transaction to be conducted before execution. Our Chief Compliance Officer (or such other person) will determine whether the transaction should be submitted to the Audit Committee for consideration. Unless the Audit Committee otherwise determines after having been notified, any proposed transaction directly between the Company and any related party transaction should be reviewed and approved by the Audit Committee prior to the time that such transaction is entered into.
While our Chief Compliance Officer (or other person) should be notified of any related party transaction that is expected to qualify as an ordinary course transaction, ordinary course transactions shall not be related person transactions and do not require Audit Committee approval under our Related Person Transactions Policy. Our Chief Compliance Officer (or such other person) shall be responsible for making the initial determination as to whether any transaction appears to be within the scope required to be disclosed pursuant to Item 404(a) of Regulation S-K or whether such transaction is, in fact, an ordinary course transaction and must take all reasonable steps to ensure that all related party transactions or any series of similar transactions required to be disclosed pursuant to Item 404(a) of Regulation S-K are presented to the Audit Committee for pre-approval or ratification, if required under the Charter of the Audit Committee, at such Committee’s next regularly scheduled meeting, or by consent in lieu of a meeting if deemed appropriate.

The Audit Committee shall review and assess the adequacy of our related party transaction policy and procedures annually and adopt any changes it deems necessary. Annually, each of our executive officers and directors shall acknowledge their familiarity and compliance with our Related Person Transaction Policy.
54

Transactions with Related Persons
Transition Services Agreement
Corvid Peak (F/K/A Tricadia)
On June 30, 2012, TAMCO, TFPFebruary 15, 2019, the Company and TricadiaCorvid Peak Holdings, L.P., Corvid Peak Capital Management, LLC, Corvid Peak Holdings GP, LLC, Corvid Peak Holdings and Corvid Peak GP Holdings LLC (collectively, “Corvid Peak”) entered into a Strategic Combination Agreement and Amended and Restated Transition Services Agreement (the “TSA”(“TSA”) in connection with the internalization. Corvid Peak is a related party of the Company because Corvid Peak is deemed to be controlled by Michael Barnes, the Company’s Executive Chairman. Tiptree agreed to invest $75 million to seed new investment funds to be managed by Corvid Peak, which amount was invested as of February 2020 in exchange for management control of TFP. TFP assignedand a profit participation in Corvid Peak. Beginning in May 2021, Corvid Peak began managing certain investment portfolio accounts of Tiptree’s insurance subsidiaries under an investment advisory agreement. We have made payments of approximately $1.98 million in management fees and incentive fees to us itsCorvid Peak for the year ended December 31, 2021 pursuant to these arrangements.

No consideration was paid for the acquisition of control by Tiptree. Tiptree will over time receive a 51% economic interest in certain profit shares interests in Corvid Peak, in increments stepping up by 10.2% each year, beginning in 2021. During the five-year period, beginning on January 1, 2026, Tiptree has the right to acquire the remaining economic interests in Corvid Peak that are held by Mr. Barnes, based upon a fair value-based formula. During the four-year period, beginning on January 1, 2027, Mr. Barnes has the reciprocal right to put his remaining economic interests in Corvid Peak to Tiptree using the same formula. Mr. Barnes has customary minority approval rights over specified actions at Corvid Peak while a Corvid Peak equity owner. Tiptree and obligations under the TSA in connectionCorvid Peak have agreed to provide each other with the Contribution Transactions. Pursuantcertain support services on an arms’-length basis, pursuant to the Transition Services Agreement, in 2015, Tricadia provided TAMCO and its affiliates, including us, withTSA. At the present time, the services consist primarily of Michael G. Barnes, our Executive Chairman, Julia Wyatt, our Chief Operating Officer, and certain backTiptree providing to Corvid Peak office administrative, information technology, insurance, legal and accounting services. The Company pays Tricadia specified prices per service. Effective as of December 31,


2015, we terminated the financial and accounting services andspace, legal and compliance services, information technology services, insurance coverage, and certain finance, accounting and tax services. As of the Transitions Services Agreement.
For the fiscal year ended December 31, 2015 the Company paid an aggregate2021, Tiptree has accrued approximately $22,638 of $2.8 million in fees to Tricadia, which includes 50,247 shares of Class A Common Stock with a grant date fair value of $285,814 under the TSA. The fees consisted of the following:
Service NameFee
Base fee for personnel, including services of our Executive Chairman and Chief Operating Officer$450,000
Incentive compensation paid to those providing services to the Company(1) 
1,743,687
Legal and compliance services150,000
Human resources information technology and other personnel112,000
Office space245,000
 $2,700,687
(1) Represents cash bonuses and grant date fair value of stock, RSUs and options granted to Tricadia or its employees providing services to Tiptree pursuant to the TSA.
Michael G. Barnes, our Executive Chairman and Chairman of our Board, is the Chairman of TFP and an equity owner of Tricadia. Mr. Barnes indirectly benefitspayments from cash and equity fees paid by the Company to TricadiaCorvid Peak under the TSA.
Geoffrey N. Kauffman, our former Co-Chief Executive Officer was also the former Co-Chief Executive Officer of TFP and remains a limited partner of Tricadia and may indirectly benefit from cash and equity fees paid by
Partner Emeritus Agreement
On December 20, 2019, the Company to Tricadia under the TSA.
Julia Wyatt, our Chief Operating Officer, is a limited partner of Tricadia and may indirectly benefit from cash and equity fees paid by the Company to Tricadia under the TSA.
Arif Inayatullah, a stockholder beneficially owning approximately 21.90%significant shareholder of the Class A common stock, is an equity owner of TricadiaCompany, entered into a partner emeritus agreement (the “Emeritus Agreement”). Under the Emeritus Agreement, Mr. Inayatullah agrees to provide advice and indirectly benefits from cash and equity fees paidother consulting services as requested by the Company’s executive committee. For these services, Mr. Inayatullah receives from the Company to Tricadiause of office space, accounting, tax, research and IT support services, one Bloomberg terminal and healthcare and other benefits consistent with that of the Company’s employees. Mr. Inayatullah will not receive any cash compensation under the TSA.Emeritus Agreement. As of December 31, 2021, Tiptree has accrued approximately $24,634 of expenses attributable to providing such benefits under the Emeritus Agreement.
Administrative Services Agreement
TFP
55


AUDIT COMMITTEE REPORT
The Audit Committee oversees our financial reporting process on behalf of our Board of Directors, in accordance with the Audit Committee charter. Management has the primary responsibility for the preparation and BackOffice Services Group, Inc. (“BOSG”) entered into an Administrative Services Agreement on June 12, 2007 (the “Administrative Services Agreement”), which was assignedpresentation and integrity of our financial statements and has represented to the Operating CompanyAudit Committee that such financial statements were prepared in accordance with generally accepted accounting principles. In fulfilling its oversight responsibilities, the Audit Committee reviewed the audited financial statements in the 2021 10-K with management, including a discussion of the quality, not just the acceptability, of the accounting principles, the reasonableness of significant judgments and the clarity of disclosures in the financial statements.
Our Audit Committee reviewed with our independent auditors, who are responsible for auditing our financial statements and for expressing an opinion on July 1, 2013the conformity of those audited financial statements with accounting principles generally accepted in connectionthe United States, their judgment as to the quality, not just the acceptability, of our accounting principles and such other matters as are required to be discussed with the Contribution Transactions,Audit Committee under which BOSG provides certain back office, administrativePublic Company Accounting Oversight Board (PCAOB) Auditing Standards. In addition, the Audit Committee has received from our independent auditors written disclosures regarding the auditors’ independence required by PCAOB Ethics and accountingIndependence Rule 3526, Communication with Audit Committees Concerning Independence, and has discussed with the independent auditors, their independence from the Company and its management. In concluding that the independent auditors are independent, the Audit Committee considered, among other factors, whether the non-audit services provided by the independent auditors were compatible with its independence.
Our Audit Committee discussed with our independent auditors the overall scope and plans for their audit. Our Audit Committee met with our independent auditors, with and without management present, to discuss the results of their examinations, and the overall quality of our financial reporting.
In reliance on the reviews and discussions referred to above, the Audit Committee recommended to our Board of Directors that the audited financial statements be included in the 2021 10-K filed with the SEC.
In addition, the Audit Committee is involved in the selection of the lead audit partner and ensures that the lead partner’s engagement is limited to no more than five consecutive years of service (in accordance with SEC rules). In 2022, pursuant to the mandated rotation, a new lead engagement partner assumed responsibilities with respect to the Company’s financial statements and other services provided to the Company, includingand he is eligible to serve in that capacity through the services of our Chief Accounting Officer. BOSG is an affiliate of Mariner. Under the Administrative Services Agreement, the Company pays BOSG a quarterly fee of 0.025%end of the Company’s Net Assets, defined as2026 audit. The prior lead Deloitte partner’s engagement began with the Company’s total assets less total liabilities, including accrued income2017 audit, and expense, calculatedhe served in accordance with GAAP. that capacity through the end of the 2021 audit.

Submitted by the Audit Committee
Paul M. Friedman (Chairman)
Lesley Goldwasser
Dominique Mielle
Bradley E. Smith
The Administrative Services Agreement has successive one year terms but mayforegoing report shall not be terminateddeemed incorporated by the Company or BOSG upon 60 days prior notice.

For the fiscal year ended December 31, 2015, we paid an aggregate of $529,000 in fees to BOSGreference by any general statement incorporating by reference this proxy statement into any filing under the Administrative Services Agreement.Securities Act, or under the Exchange Act, except to the extent that we specifically incorporate this information by reference, and shall not otherwise be deemed filed under such Securities Act or Exchange Act.
Tricadia and Mariner are parties to a services agreement under which Mariner receives a portion of Tricadia’s revenues, in return for which Mariner provides certain support services to Tricadia and its affiliates, including back office, human resources, marketing, compliance, legal support, and investor relations.

56


ADDITIONAL INFORMATION


ADDITIONAL INFORMATION
Solicitation of Proxies
We will pay the cost of solicitation of proxies. In addition to the solicitation of proxies by mail, our directors, officers and employees may also solicit proxies personally or by telephone without additional compensation for such activities. We may also request persons, firms and corporations holding shares in their names or in the names of their nominees, which are beneficially owned by others, to send proxy materials to and obtain proxies from such beneficial owners. We will reimburse such holders for their reasonable expenses. We have hired Morrow to help us distribute and solicit proxies. We will pay approximately $5,000$2,500 in fees, plus expenses and disbursements, to Morrow for its proxy solicitation services.
Stockholder Proposals
Proposals for Inclusion in the Proxy Statement.    
Tiptree welcomes comments or suggestions from its stockholders. Under the Exchange Act, if a stockholder wants to include a proposal for consideration in our proxy statement and on proxy card with respect to our 2017 annual meeting2023 Annual Meeting of stockholders, the proposal must be received in writing at Tiptree Financial Inc., 780 Third299 Park Avenue, 21st13th Floor, New York, NY 10017,New York 10171, Attn: Secretary, no later than 5:00 p.m., Eastern Time, on December 28, 2016.23, 2022. Such proposals must comply with all applicable requirements of Rule 14a-8 promulgated under the Exchange Act (“Rule 14a-8”) and our Bylaws.
Proposals to be Offered at an Annual Meeting. 
Article II, Section 10 of our Third Amended and Restated Bylaws provides certain procedures that a stockholder must follow to nominate persons for election as directors or to introduce an item of business at an annual meeting if such matter is not intended to be considered for inclusion in our proxy statement pursuant to Rule 14a-8. These procedures provide that such nominations for director nominees and/or items of business must be submitted in writing to the Secretary of the Company at Tiptree Financial Inc., 780 Third299 Park Avenue, 21st13th Floor, New York, NY 10017,New York 10171, Attn: Secretary and must be received by the Secretary no earlier than November 28, 201623, 2022 and no later than 5:00 p.m., Eastern Time, on December 28, 2016.23, 2022.
If the 20172023 Annual Meeting is not within 30 days before or 60 days after the anniversary of this year’s Annual Meeting, we must receive notice no earlier than the 150th day prior to such meeting and not later than the close of business5:00 p.m., Eastern Time, on the later of the 120th day prior to such meeting or the 10th day following the public announcement of the meeting date. If a shareholderstockholder does not meet these deadlines, or does not satisfy the requirements of Rule 14a-8, the persons named as proxies will be allowed to use their discretionary voting authority when and if the matter is raised at the Annual Meeting.
Householding of Proxy Materials
The SEC has adopted rules that permit companies and intermediaries (such as banks and brokers) to satisfy the delivery requirements for proxy statements and annual reports with respect to two or more stockholders sharing the same address by delivering a single proxy statement addressed to those stockholders. This process, which is commonly referred to as “householding,” potentially means extra convenience for stockholders and cost savings for companies.
This year, a number of brokers with account holders who are our stockholders will be “householding” our proxy materials. A single proxy statement will be delivered to multiple stockholders sharing an address unless contrary instructions have been received from the impacted stockholders. Once you have received notice from your broker that they will be “householding” communications to your address, “householding” will continue until you are notified otherwise or until you revoke your consent. If you did not respond that you did not want to participate in householding, you were deemed to have consented to the process. Stockholders may revoke their consent at any
57


time in writing to Tiptree Financial Inc., 780 Third299 Park Avenue, 21st13th Floor, New York, NY 10017,New York 10171, Attn: Secretary or by calling our corporate number at (212) 446-1400.
Upon request, we will promptly deliver a separate copy of this proxy statement, the Annual Report and any other proxy materials to any stockholder at a shared address to which a single copy of any of those documents was delivered. Stockholders may request a separate copy of this proxy statement, the Annual Report or any other proxy materials by writing to Tiptree Financial Inc., 780 Third299 Park Avenue, 21st13th Floor, New York, NY 10017,New York 10171, Attn: Secretary or by calling our corporate number at (212) 446-1400. In addition, if you are receiving multiple copies of this proxy statement, Annual Report or other proxy materials, you can request householding by contacting our Secretary in the same manner.
OTHER MATTERS
Our Board of Directors does not know of any matters other than those described in this proxy statement that will be presented for action at the Annual Meeting. If other matters are presented, proxies will be voted in accordance with the best judgmentdiscretion of the proxy holders.
By Order of our Board of Directors
/s/ Neil C. Rifkind
Neil C. Rifkind
Tiptree Inc.
Vice President, General Counsel and Secretary
New York, New York
April 27, 2016

22, 2022

58



ANNEX A

Amendment to Tiptree Inc.
2017 Omnibus Incentive Plan

RECITALS

WHEREAS, the Company has previously adopted, and the Company’s stockholders have previously approved, the Tiptree Inc. 2017 Omnibus Incentive Plan (as amended from time to time, the “Plan”);

WHEREAS, pursuant to Section 12.1 of the Plan, the Board has the authority to amend the Plan to increase the maximum aggregate number of shares of Common Stock available for issuance in satisfaction of Awards thereunder (the “Share Limit”), subject to approval of the Company’s stockholders;

WHEREAS, the Board believes it is in the best interests of the Company and its stockholders to amend the Plan to increase the Share Limit under the Plan as set forth herein; and

WHEREAS, this Amendment shall become effective upon the approval of this Amendment by the Company’s stockholders (the date of such approval, the “Effective Date”).

NOW, THEREFORE, BE IT RESOLVED, that the Plan is hereby amended as follows, effective as of the Effective Date:

AMENDMENT

1.The first sentence of Section 3.1 of the Plan is hereby deleted and replaced in its entirety with the following:

“Number of Shares. (a) Subject to adjustment as provided in Section 12.2, a total of 10,100,000 Shares shall be     authorized for issuance in satisfaction of Awards under the Plan.”
2.This Amendment shall be and is hereby incorporated into and forms a part of the Plan.

3.Except as expressly provided herein, all terms and conditions of the Plan shall continue in full force and effect.
59

ANNEX B: NON-GAAP MEASURES

Non-GAAP Financial Measures — Adjusted net income and Adjusted return on average equity

The Company defines Adjusted net income as income before taxes, less provision (benefit) for income taxes, and excluding the after-tax impact of various expenses that we consider to be unique and non-recurring in nature, including merger and acquisition related expenses, stock-based compensation, net realized and unrealized gains (losses) and intangibles amortization associated with purchase accounting. We use adjusted net income as an internal operating performance measure in the management of business as part of our capital allocation process. We believe adjusted net income provides useful supplemental information to investors as it is frequently used by the financial community to analyze financial performance between periods and for comparison among companies. Adjusted net income should not be viewed as a substitute for income before taxes calculated in accordance with GAAP, and other companies may define adjusted net income differently.

We define Adjusted return on average equity as Adjusted net income expressed on an annualized basis as a percentage of average beginning and ending stockholder’s equity during the period. We use Adjusted return on average equity as an internal performance measure in the management of our operations because we believe it gives our management and other users of our financial information useful insight into our results of operations and our underlying business performance. Adjusted return on average equity should not be viewed as a substitute for return on average equity calculated in accordance with GAAP, and other companies may define adjusted return on average equity differently.
Year Ended December 31, 2021
Tiptree Capital
($ in thousands)InsuranceMortgageOtherCorporateTotal
Income (loss) before taxes$69,857 $28,407 $17,210 $(50,132)$65,342 
Less: Income tax (benefit) expense(18,438)(4,882)(1,992)4,021 (21,291)
Less: Net realized and unrealized gains (losses)(3,732)(5,798)(3,091)— (12,621)
Plus: Intangibles amortization (1)
15,329 — — — 15,329 
Plus: Stock-based compensation expense2,006 331 213 8,581 11,131 
Plus: Non-recurring expenses2,158 — 938 2,171 5,267 
Plus: Non-cash fair value adjustments— — (3,170)— (3,170)
Less: Tax on adjustments(398)(624)655 4,249 3,882 
Adjusted net income$66,782 $17,434 $10,763 $(31,110)$63,869 
Adjusted net income$66,782 $17,434 $10,763 $(31,110)$63,869 
Average stockholders’ equity$300,820 $60,433 $113,717 $(88,111)$386,859 
Adjusted return on average equity22.2 %28.8 %9.5 %NM%16.5 %

60

Year Ended December 31, 2020
Tiptree Capital
($ in thousands)InsuranceMortgageOtherCorporateTotal
Income (loss) before taxes$26,948 $31,102 $(61,242)$(35,660)$(38,852)
Less: Income tax (benefit) expense(3,725)(7,066)13,624 10,794 13,627 
Less: Net realized and unrealized gains (losses)13,804 4,018 67,668 — 85,490 
Plus: Intangibles amortization (1)
9,213 — — — 9,213 
Plus: Stock-based compensation expense2,287 2,482 174 3,172 8,115 
Plus: Non-recurring expenses3,418 — 624 758 4,800 
Plus: Non-cash fair value adjustments— — (2,141)— (2,141)
Less: Tax on adjustments(8,522)(1,958)(14,210)(4,131)(28,821)
Adjusted net income$43,423 $28,578 $4,497 $(25,067)$51,431 
Adjusted net income$43,423 $28,578 $4,497 $(25,067)$51,431 
Average stockholders’ equity285,760 47,202 138,606 (79,092)392,476 
Adjusted return on average equity15.2 %60.5 %3.2 %NM%13.1 %
___________________________
Notes
(1)Specifically associated with acquisition purchase accounting. See Note (3) Acquisitions, in our Annual Report on Form 10-K for the year ended December 31, 2021.

Non-GAAP Financial Measures — Adjusted EBITDA

The Company defines Adjusted EBITDA as GAAP net income of the Company plus corporate interest expense, plus income taxes, plus depreciation and amortization expense, less the effects of purchase accounting, plus non-cash fair value adjustments, plus significant non-recurring expenses, and plus unrealized gains (losses) on available for sale securities reported in other comprehensive income. Adjusted EBITDA is used to determine incentive compensation for the Company’s executive officers. Adjusted EBITDA is not a measurement of financial performance or liquidity under GAAP and should not be considered as an alternative or substitute for GAAP net income.
61

($ in thousands)For the Year Ended December 31,
20212020
Net income (loss) attributable to common stockholders$38,132 $(29,158)
Add: net (loss) income attributable to non-controlling interests5,919 3,933 
Corporate debt related interest expense(1)
24,426 23,322 
Consolidated provision (benefit) for income taxes21,291 (13,627)
Depreciation and amortization24,437 17,268 
Non-cash fair value adjustments(2)
(7,945)(7,122)
Non-recurring expenses(3)
5,267 4,800 
Unrealized gains (losses) on AFS securities(10,751)5,125 
Adjusted EBITDA$100,776 $4,541 
(1)Corporate debt interest expense includes interest expense from secured corporate credit agreements, junior subordinated notes and preferred trust securities. Interest expense associated with asset-specific debt is not added-back for Adjusted EBITDA.
(2)For maritime transportation operations, depreciation and amortization is deducted as a reduction in the value of the vessel.
(3)Acquisition, start-up and disposition costs, including debt extinguishment, legal, taxes, banker fees and other costs.

Non-GAAP Financial Measures — Book value per share

Management believes the use of this financial measure provides supplemental information useful to investors as book value is frequently used by the financial community to analyze company growth on a relative per share basis. The following table provides a reconciliation between total stockholders’ equity and total shares outstanding, net of treasury shares.
 ($ in thousands, except per share information)
As of December 31,
20212020
Total stockholders’ equity$400,181 $373,538 
Less: Non-controlling interests17,227 17,394 
Total stockholders’ equity, net of non-controlling interests$382,954 $356,144 
Total common shares outstanding34,124 32,682 
Book value per share$11.22 $10.90 

62


TIPTREE FINANCIAL INC.
780 THIRD AVENUEC/O BROADRIDGE
21ST FLOORP.O. BOX 1342
NEW YORK,BRENTWOOD, NY 1001711717
VOTE BY INTERNET - www.proxyvote.com
Use the Internet to transmit your voting instructions and for electronic delivery of information up until 11:59 PM Eastern TimeP.M. ET on June 5, 2016.6, 2022. Have your proxy card in hand when you access the web sitewebsite and follow the instructions to obtain your records and to create an electronic voting instruction form.
During the Meeting - Go to www.virtualshareholdermeeting.com/TIPT2022
  
ELECTRONIC DELIVERY OF FUTURE PROXY MATERIALS
If you would like to reduce the costs incurred by our company in mailing proxy materials, you can consent to receiving all future proxy statements, proxy cards and annual reports electronically via e-mail or the Internet. To sign up for electronic delivery, please follow the instructions above to vote using the Internet and, when prompted, indicate that you agree to receive or access proxy materials electronically in future years.
VOTE BY PHONE - 1-800-690-6903
Use any touch-tone telephone to transmit your voting instructions up until 11:59 PM Eastern TimeP.M. ET on June 5, 2016.6, 2022. Have your proxy card in hand when you call and then follow the instructions.
VOTE BY MAIL
Mark, sign and date your proxy card and return it in the postage-paid envelope we have provided or return it to Tiptree Financial Inc., Vote Processing, c/o Broadridge, 51 Mercedes Way, Edgewood, NY 11717.
TO VOTE, MARK BLOCKS BELOW IN BLUE OR BLACK INK AS FOLLOWS:  ý
   M41506-P22275   KEEP THIS PORTION FOR YOUR RECORDS
  IF VOTING BY MAIL DETACH AND RETURN THIS PORTION ONLY
THIS PROXY CARD IS VALID ONLY WHEN SIGNED AND DATED.
TIPTREE FINANCIAL INC.For
All
Withhold

All
  
For All

Except
  To withhold authority to vote for any individual nominee(s), mark “For All Except” and write the number(s) of the nominee(s) on the line below.
The Board of Directors recommends you vote “FOR ALL” on the following proposal:¨¨  ¨  ________________________
Vote on Directors      
1.     Election of two Class III Directors  
Nominees:      
01) Jonathan IlanyLesley Goldwasser
02) Lesley GoldwasserJonathan Ilany
Vote on Proposals      
Vote on Proposal
The Board of Directors recommends you vote “FOR” the following proposal:proposals:  For  Against  Abstain
2. To approve an amendment to the Company’s 2017 Omnibus Incentive Plan to increase the number of shares of the Company’s common stock available for awards thereunder by an additional 4,000,000 shares.¨¨¨
3.     To ratify the selection of KPMGDeloitte & Touche LLP as our independent registered public accounting firm for the fiscal year ending December 31, 2016.2022.¨  ¨  ¨
NOTE: To conduct such other business as may properly come before the meeting or any adjournment or postponement thereof.
        
 



Please sign exactly as your name(s) appear(s) hereon. When signing as attorney, executor, administrator, or other fiduciary, please give full title as such. Joint owners should each sign personally. All holders must sign. If a corporation or partnership, please sign in full corporate or partnership name by duly authorized officer.

    
        
Signature [PLEASE SIGN WITHIN BOX]

 
Date  

  
Signature (If held jointly)

 
Date

63











--------------------------------------------------------------------------------------------------------------------------------------------


Important Notice Regarding the Availability of Proxy Materials for the Stockholders Meeting
to be Held on
June 6, 2016:

7, 2022:
The Notice and Proxy Statement and the Annual Report on Form 10-K are available at www.proxyvote.com.
M41507-P22275        
 
-------------------------------------------------------------------------------------------------------------------------------------------
 
TIPTREE FINANCIAL INC.
ANNUAL MEETING OF STOCKHOLDERS
June 6, 20167, 2022,
9:30 AM Local4:00 PM Eastern Standard Time
 
This proxy card is solicited on behalf of
The Board of Directors for the Annual Meeting of Stockholders on June 6, 20167, 2022,
 
The undersigned hereby appoints Sandra Bell and Neil C. Rifkind, and each of them, as proxies, with full power of substitution, to represent and vote all of the undersigned’s shares of Tiptree Financial Inc. common stock held of record as of the close of business on April 18, 201614, 2022 at the virtual Annual Meeting of Stockholders to be held via live audio webcast at www.virtualshareholdermeeting.com/TIPT2022 on Monday,Tuesday, June 6, 20167, 2022, at 9:30 a.m. local time at 780 Third Avenue, 21st Floor, New York, NY 10017, and4:00 p.m. EST, subject to any adjournments or postponements thereof, upon all subjects that may properly come before the meeting, including the matters described in the proxy statement furnished herewith, subject to any direction indicated on the reverse side of this card.

The shares of common stock you beneficially own will be voted as you specify. If no directions are given, the proxies will vote “FOR ALL” nominees in Proposal 1 and “FOR” Proposal 2.Proposals 2 and 3.
 
In the event that (i) any nominee herein becomes unable or unwilling to serve, or (ii) any other matter properly comes before the meeting, the proxies are authorized to vote in the manner recommended by the Board of Directors for such vote or, if no recommendation is made, in the discretion of the proxies.
 
Please mark, sign and date this proxy card and return it promptly in the enclosed postage-paid envelope so that the shares may be represented at the Annual Meeting.
 
Continued and to be signed on reverse side