UNITED STATES

SECURITIES AND EXCHANGE COMMISSION

WASHINGTON,Washington, D.C. 20549

 

SCHEDULE 14A

(RULE 14a-101)Proxy Statement Pursuant to Section 14(a) of the

INFORMATION REQUIRED IN PROXY STATEMENT

SCHEDULE 14A INFORMATION

PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE

SECURITIES EXCHANGE ACT OFSecurities Exchange Act of 1934

(Amendment No.     )

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 Definitive Proxy Statement
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 Soliciting Material Pursuant to Section 240.14a-12§240.14a-12

Heritage Insurance Holdings, Inc.

(Name of Registrant as Specified In Its Charter)

(Name of Person(s) Filing Proxy Statement, if Other Thanother than the Registrant)

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LOGOLOGO

HERITAGE INSURANCE HOLDINGS, INC.Heritage Insurance Holdings, Inc.

2600 MCCORMICK DRIVE, SUITEMcCormick Drive Suite 300 CLEARWATER, FLORIDA

Dear FellowClearwater, Florida 33759

April 24, 2018

To Our Stockholders:

On behalf of the Board of Directors and management of Heritage Insurance Holdings, Inc., a Delaware corporation (“Heritage,” the “Company,” “we,” “us” or “our”), we cordially invite you to join us at a specialattend the annual meeting of stockholders of the Company, which willto be held on December 1, 2017,June 22, 2018, at 10:00 a.m. (ET), Eastern Time, at 2600 McCormick Drive, Suite 300, Clearwater,the Grand Hyatt Tampa Bay, 2900 Bayport Dr., Tampa, Florida 33759 (the “Special Meeting”).33607.

On August 16, 2017,The following pages contain the Company completed the offering (the “Offering”) of $125,000,000 aggregate principal amount of 5.875% convertible senior notes due 2037 (the “Convertible Notes”) in a private placement transaction pursuant to Rule 144A under the Securities Act of 1933, as amended (the “Securities Act”), with Citigroup Global Markets Inc., as the initial purchaser (the “Initial Purchaser”). On September 7, 2017, the Company completed a private placement of an additional $11,750,000 aggregate principal amountformal notice of the Convertible Notesannual meeting, the proxy statement and the proxy card. Please review this material for information concerning the business to be conducted at the Initial Purchaser. meeting and the nominees for election as directors.

The total net proceeds from the offering, after deducting discounts, commissions and estimated offering expenses payable by the Company, were approximately $132.0 million. The Company utilized approximately $40 millionpurpose of the proceeds to repurchase shares of the Company’s common stock. The Company intends to use the remainder of the net proceeds from the Offering to finance the cash portion of the acquisition of NBIC Holdings, Inc., the parent company of Narragansett Bay Insurance Company, whichmeeting is expected to close as early as the fourth quarter of 2017.

The conversion of all of the outstanding Convertible Notes into common stock would result in the issuance of more than 20% of the Company’s voting power and shares of common stock outstanding prior to such issuance which, as described below, requires stockholder approval under the rules of the New York Stock Exchange (the “NYSE”). Accordingly, the Convertible Notes currently are convertible only into cash unless and until stockholder approval is obtained.

Because the Company’s common stock is listed on the NYSE, the Company is subject to the NYSE’s rules and regulations. Rule 312.03(c) of the NYSE Listed Company Manual (“NYSE Rule 312.03(c)”) requires stockholder approval prior to the issuance of common stock, or securities convertible into or exercisable for common stock, in any transaction or series of transactions if (i) the common stock to be issued has, or will have upon issuance, voting power equal to or in excess of 20% of the voting power outstanding before the issuance of such stock or of securities convertible into or exercisable for common stock, or (ii) the number of shares of common stock to be issued is, or will be upon issuance, equal to or in excess of 20% of the number of shares of common stock outstanding before the issuance of the common stock or of securities convertible into or exercisable for common stock (the “Issuance Proposal”). If the Company obtains stockholder approval, the Convertible Notes will be convertible, subject to various conditions and during certain periods, into cash, shares of the Company’s common stock or a combination of cash and shares of the Company’s common stock, at the Company’s election. If the Issuance Proposal is not approved in accordance with NYSE Rule 312.03(c) prior to the relevant conversion date, the Company will be required to pay to holders in respect of each $1,000 principal amount of Convertible Notes being converted solely an amount in cash as if the Company had elected a “cash settlement.”


At the Special Meeting, in accordance with NYSE Rule 312.03(c), you will be asked to consider and vote on a proposalupon proposals to approve(i) elect ten directors who have been nominated for election, (ii) ratify the Issuance Proposal.

Unless and until the Issuance Proposal is approved by the Company’s stockholders, the conversion option that is part of the Convertible Notes will be accounted for as a derivative liability pursuant to accounting standards relating to derivative instruments and hedging activities (notwithstanding other factors to be evaluated by the Company each reporting period regarding the classification of derivative instruments).

For each financial statement period after issuance of the Convertible Notes, a hedge gain (or loss) will be reported in the Company’s income statement to the extent the valuation of the derivative liability changes from the previous period as a result of changes in the market price of the Company’s common stock or changes in other valuation inputs and assumptions. For example, if the stock price increases, the value of the option increases and there would be a hedge loss reported in the period. This could result in significant fluctuations in the Company’s consolidated statement of comprehensive income (loss) from period to period and have a material adverse effect on the Company’s earnings per share. In addition, if the Company is required to settle its obligations in respect of the Convertible Notes solely in cash, the Company’s cash flow and liquidity position could be adversely impacted.

Our Board of Directors believes that the Issuance Proposal is in the best interests of the Company and its stockholders and, therefore, recommends that you vote “FOR” the Issuance Proposal.

The proxy statement attached to this letter provides you with information about the Issuance Proposal and the Special Meeting of the Company’s stockholders. We encourage you to read the entire proxy statement carefully. You may also obtain more information about the Company from documents we have filed with the U.S. Securities and Exchange Commission. See “Where You Can Find Additional Information” in the accompanying proxy statement.

Regardless of the number of sharesappointment of our common stock you own, your vote is important. Whether or not you plan to attend the Special Meeting, please take the time to submit a proxy by following the instructions on your proxy card as soon as possible. You may do soby completing, signing, dating,independent registered public accounting firm for 2018 and returning the enclosed proxy card by mail, or you may submit your proxy by telephone or electronically through the Internet, as further described on the proxy card. If your shares of common stock are held in an account at a broker, dealer, commercial bank, trust company, or other nominee, you should instruct such broker or other nominee how to vote in accordance with the voting instruction form furnished by such broker or other nominee.

Voting by proxy will not prevent you from voting your shares in person if you subsequently choose to attend the Special Meeting.

Thank you for your cooperation and continued support.

Sincerely,

Bruce Lucas

Chairman & Chief Executive Officer

October 31, 2017

THE ACCOMPANYING PROXY STATEMENT IS DATED OCTOBER 31, 2017 AND IS FIRST BEING MAILED TO STOCKHOLDERS ON OR ABOUT OCTOBER 31, 2017.


HERITAGE INSURANCE HOLDINGS, INC.

2600 MCCORMICK DRIVE, SUITE 300

CLEARWATER, FLORIDA

NOTICE OF SPECIAL MEETING OF STOCKHOLDERS

To Be Held on December 1, 2017

To the Stockholders of Heritage Insurance Holdings, Inc.:

Notice is hereby given that a special meeting (the “Special Meeting”) of stockholders of Heritage Insurance Holdings, Inc. (the “Company”) will be held on December 1, 2017, at 10:00 a.m., Eastern Time, at 2600 McCormick Drive, Suite 300, Clearwater, Florida 33759:

1. To consider and vote on a proposal to approve, pursuant to Rule 312.03(c) of the New York Stock Exchange Listed Company Manual, the issuance of our common stock upon the conversion of our Convertible Notes (the “Issuance Proposal”);

2. To consider and vote on a proposal to adjourn or postpone the Special Meeting, if necessary, to solicit additional proxies (the “Adjournment Proposal” and together with the Issuance Proposal, the “Proposals”); and

3. To(iii) transact such other business as may properly come before the Special Meetingmeeting.

We are pleased to take advantage of the Securities and any adjournmentsExchange Commission rules that allow issuers to furnish proxy materials to their stockholders on the Internet. We believe these rules allow us to provide you with the information you need while lowering the costs of delivery and reducing the environmental impact of our annual meeting. The proxy statement contains instructions on how you can request a paper copy of the proxy statement and annual report.

Whether or postponements thereof.not you plan to attend the meeting, your vote is important and we encourage you to vote promptly. You may vote your shares via a toll-free telephone number, over the Internet or by mail if you request a proxy card in writing. Instructions regarding these methods of voting are contained on the notice regarding the availability of proxy materials for the annual meeting of stockholders to be held on June 22, 2018.

The Company’sWe look forward to seeing you at the meeting.

Sincerely yours,

Bruce Lucas

Chairman and Chief Executive Officer


LOGO

Heritage Insurance Holdings, Inc.

2600 McCormick Drive Suite 300

Clearwater, Florida 33759

June 22, 2018, 10:00 a.m. (ET)

April 24, 2018

To Our Stockholders:

Notice is hereby given that the annual meeting of the stockholders of Heritage Insurance Holdings, Inc. (the “Company”), a Delaware corporation, will be held on June 22, 2018, at 10:00 a.m. (ET), at the Grand Hyatt Tampa Bay, 2900 Bayport Dr., Tampa, Florida 33607:

to elect ten members of the Board of Directors recommends thatto serve until the 2019 annual meeting of stockholders or until their respective successors are elected and qualified;

to ratify the appointment of Grant Thornton LLP as the independent registered public accounting firm for the Company for the fiscal year ending December 31, 2018; and

to transact such other business as may properly come before the meeting.

These items of business, including the nominees for director, are more fully described in the proxy statement accompanying this notice. The Board of Directors has fixed the close of business on April 23, 2018 as the record date for determining the stockholders entitled to notice of and to vote FOR” each ofat the Issuance Proposalannual meeting and any adjournment or postponement thereof.

All stockholders are cordially invited to attend the Adjournment Proposal.

annual meeting in person. However, whether or not you plan to attend the annual meeting in person, we urge you to vote your shares via the toll-free telephone number or over the Internet, as described in the enclosed materials. If you submit your proxy and then decide to attend the annual meeting to vote your shares in person, you may still do so. Your proxy is revocable in accordance with the procedures set forth in the proxy statement. Only stockholders of record of our common stock as of the close of business on October 16, 2017, the “Record Date,”April 23, 2018 are entitled to receive notice of, and to vote at, the Special Meetingattend and at any adjournment or postponement of the Special Meeting. Only matters referred to in this notice of the Special Meeting, and those which are incidental and germane to such matters, may be discussed.

The approval of the Issuance Proposal requires the affirmative vote of a majority of the shares of our common stock voting thereon at a meeting at which a quorum is present. The approval of the Adjournment Proposal requires the affirmative vote of a majority of the shares of our common stock present and entitled to vote at, the Special Meeting, whether or not a quorum is present.

Even if you plan to attend the Special Meeting in person, we request that you submit a proxy by following the instructions on your proxy card as soon as possible and thus ensure that your shares will be represented at the Special Meeting if you are unable to attend. Please do so by completing, signing, dating, and returning the enclosed proxy card by mail, or you may submit your proxy by telephone or electronically through the Internet, as further described on the proxy card. If you sign, date, and return your proxy card without indicating how you wish to vote, your vote will be counted as a vote “FOR” the Issuance Proposal (and, if necessary and appropriate, the Adjournment Proposal). If your shares are held in an account at a broker, dealer, commercial bank, trust company, or other nominee, you should instruct such broker or other nominee how to vote in accordance with the voting instruction form furnished by such broker or other nominee.

Whether you attend the Special Meeting or not, any proxy given pursuant to this solicitation may be revoked by the person giving it at any time before it is voted. A proxy may be revoked in writing to the


Company’s Corporate Secretary, at or before taking of the vote at the Special Meeting. A written notice of revocation or a duly executed proxy, in either case dated later than the prior proxy relating to the same shares will be treated as the final vote.

A proxy may also be revoked by attending the Special Meeting and voting in person, although attendance at the Special Meeting will not itself revoke a proxy. Any written notice of revocation or subsequent proxy should be sent so as to be delivered to Steven Martindale, Chief Financial Officer and Secretary, Heritage Insurance Holdings, Inc., 2600 McCormick Drive, Suite 300, Clearwater, Florida 33759, or hand delivered to Steven Martindale, at or before the taking of the vote at the Special Meeting.

If you hold your shares through a broker, dealer, commercial bank, trust company or other nominee, you should follow the instructions of such broker or other nominee regarding revocation of proxies.

Your vote is important. Whether or not you plan to attend the Special Meeting in person, it is important that your shares be represented. We ask that you vote your shares as soon as possible.meeting.

 

By Order of the Board of Directors,

Steven MartindaleKirk Lusk

Chief Financial Officer and Secretary

Clearwater, FloridaImportant Notice Regarding the Availability of Proxy Materials

October 31,for the Annual Meeting of Stockholders to be Held on June 22, 2018

Our Proxy Statement and 2017

Annual Report are available athttp://www.edocumentview.com/HRTG.


SUMMARY VOTING INSTRUCTIONS

Ensure that your shares of our common stock can be voted at the Special Meeting by submitting your proxy or contacting your broker, dealer, commercial bank, trust company, or other nominee.

If your shares are registered directly in your name with the Company’s transfer agent, Computershare Investor Services, you are considered a stockholder of record with respect to those shares. If your shares are held in a bank or brokerage account, you are considered the beneficial owner of those shares.

If you are a stockholder of record, you will receive only one notice or proxy card for all the shares you hold in certificate form, book-entry form, and in any Company benefit plan.

If you are a beneficial owner, you will receive voting instruction information from the bank, broker or other nominee through which you own your shares of common stock.

If you sign, date, and return your proxy card without indicating how you wish to vote, your vote will be counted as a vote “FOR” the Issuance Proposal and, if necessary and appropriate, the Adjournment Proposal.

For additional questions regarding the Issuance Proposal, assistance in submitting proxies or voting shares of our common stock, or toYou may also request additionalhard copies of the proxy statement or the enclosed proxy card, please contact these documents free of charge by writing to:

Investor Relations, Heritage Insurance Holdings, Inc., 2600 McCormick Drive Suite 300, Clearwater, Florida 33759, telephone: (727) 362-7200 or Georgeson LLC, telephone: 1 (877) 278-9670 (toll free).33759.


The date of this proxy statement is April 24, 2018, and it is being delivered to stockholders on or about May 7, 2018.

PROXY SUMMARY

This summary highlights information contained elsewhere in this proxy statement. This summary does not contain all of the information you should consider, and you should read the entire proxy statement carefully before voting.

Annual Meeting and Voting Information

Date and Time:

Friday, June 22, 2018 at 10:00 a.m. (ET)

Location:

The Grand Hyatt Tampa Bay, 2900 Bayport Dr., Tampa, Florida 33607

Admission:

When you arrive at the annual meeting, you must present photo identification, such as a driver’s license.Beneficialownersmustalsoprovideevidenceofstockholdings,suchasarecentbrokerageaccountorbankstatement.

Record Date:

April 23, 2018

Voting:

Each share of common stock entitles you to one vote on each matter to be voted on at the annual meeting. Cumulative voting is not permitted.

Items to be Voted on at the 2018 Annual Meeting of Stockholders

Proposal

Board of Directors’
Recommendation

•  Elect ten members of the Board of Directors to serve until the 2019 annual meeting of stockholders or until their respective successors are elected and qualified.

FOR

•  Ratify the appointment of Grant Thornton LLP as the independent registered public accounting firm for the Company for the fiscal year ending December 31, 2018.

FOR

Director Nominees

Name

Director
Since
IndependentCommittee Memberships
ACCCCGN

Bruce Lucas (Chairman and Chief Executive Officer (“CEO”))

2014No

Richard Widdicombe (President)

2012No

Panagiotis (Pete) Apostolou

2012Yes

Irini Barlas

2014YesC, FM

Trifon Houvardas

2012YesM

Steven Martindale

2018No

James Masiello

2014YesCM

Nicholas Pappas

2014YesMC

Joseph Vattamattam

2014Yes

Vijay Walvekar

2012YesMM

AC

Audit Committee

C

Chair

CC

Compensation Committee

M

Member

CGN

Corporate Governance and Nominating Committee

F

Financial expert

Corporate Governance

We are committed to high standards of ethical and business conduct and strong corporate governance practices. This commitment is highlighted by the practices described below.

AnnualElections: Our directors are elected annually for one year terms.


DirectorIndependence: Seven of our ten director nominees are independent, and our key Board committees (Audit Committee, Compensation Committee and Corporate Governance and Nominating Committee) are comprised entirely of independent directors.

NoShareholderRightsPlan. We do not currently have in place, nor have we ever had, a shareholder rights plan, commonly known as a “poison pill.”


Proxy Statement for the Annual Meeting of Stockholders of

HERITAGE INSURANCE HOLDINGS, INC.

To Be Held on June 22, 2018

TABLE OF CONTENTS

 

Page

PROXY STATEMENT

   1 

QUESTIONS AND ANSWERS ABOUT THE SPECIAL MEETING AND THE PROPOSALSAnnual Meeting Information

   1 

Voting Information

1

ISSUANCE PROPOSAL—APPROVALPROPOSALS TO BE VOTED ON

3

Proposal 1: Election of Directors

3

Proposal 2: Ratification of Appointment of Independent Registered Public Accounting Firm

5

BOARD OF THE ISSUANCE OF COMPANY COMMON STOCK UPON CONVERSION OF THE CONVERTIBLE NOTESDIRECTORS AND CORPORATE GOVERNANCE

5

Board Leadership Structure

5

Board of Directors Role in Risk Oversight

6

Meetings and Committees of the Board of Directors

6

Director Independence

7

Governance Documents

7

Communications with Directors

7

Attendance at Annual Meeting

   8 

EXECUTIVE OFFICERS

8

ADJOURNMENT PROPOSAL—APPROVAL OF THE ADJOURNMENT OR POSTPONEMENT OF THE SPECIAL MEETINGSTOCK OWNERSHIP

9

Security Ownership of Certain Beneficial Owners and Management

9

Section 16(a) Beneficial Ownership Reporting Compliance

11

CERTAIN RELATIONSHIPS AND RELATED PARTY TRANSACTIONS

11

EXECUTIVE COMPENSATION

   12 

SECURITY OWNERSHIP OF CERTAIN BENEFICIAL OWNERS AND MANAGEMENT

13

OTHER MATTERSDIRECTOR COMPENSATION

   15 

PROXY SOLICITATION AND COSTS

15

WHERE YOU CAN FIND MORE INFORMATION

15

INFORMATION INCORPORATED BY REFERENCE

15

AVAILABILITY OF FORM 10-K AND ANNUALAUDIT COMMITTEE REPORT TO STOCKHOLDERS

   16 

FEES BILLED FOR SERVICES RENDERED BY PRINCIPAL REGISTERED PUBLIC ACCOUNTANTS

17

OTHER INFORMATION

17

Stockholder Proposals for the 2019 Annual Meeting

17

Expenses of Solicitation

17

“Householding” of Proxy Materials

17

Important Notice Regarding the Availability of Proxy Materials for the Special

Meeting of Stockholders to be Held on December 1, 2017

This Proxy Statement is available, free of charge, at http://www.investorvote.com/HRTG.

i


LOGO

2600 McCormick Drive Suite 300

Clearwater, Florida 33759

PROXY STATEMENT

This proxy statement sets forth information relating toand enclosed proxy card are being furnished commencing on or about May 7, 2018 in connection with the solicitation of proxies by the Board of Directors of Heritage Insurance Holdings, Inc. (the “Company”) in connection with, a Delaware corporation. In this proxy statement, we refer to Heritage Insurance Holdings, Inc. as the Company’s special“Company,” “we,” “our” or “us” and the Board of Directors as the “Board.” We are sending the proxy materials because the Board is seeking your permission (or proxy) to vote your shares at the annual meeting of stockholders (the “Special Meeting”) or any adjournment or postponement of the Special Meeting.on your behalf. This proxy statement presents information that is being furnished by our Boardintended to help you in reaching a decision on voting your shares of Directors for usecommon stock. Only stockholders of record at the Specialclose of business on April 23, 2018, the record date, are entitled to vote at the meeting, with each share entitled to one vote. We have no other voting securities.

Annual Meeting of stockholders to be held atInformation

DateandLocation. We will hold the annual meeting on December 1, 2017June 22, 2018, at 10:00 a.m. (ET), Eastern Time. This proxy statement and format the Grand Hyatt Tampa Bay, 2900 Bayport Dr., Tampa, Florida 33607.

Admission. Only record or beneficial owners of proxy are first being mailed to stockholders onthe Company’s common stock or about October 31, 2017, to our stockholderstheir proxies may attend the annual meeting in person. When you arrive at the annual meeting, you must present photo identification, such as a driver’s license.Beneficial owners must also provide evidence of stock holdings, such as a recent brokerage account or bank statement.

Voting Information

RecordDate. The record date for the annual meeting is April 23, 2018. You may vote all shares of the Company’s common stock that you owned as of the close of business on October 16, 2017 (the “Record Date”).

QUESTIONS AND ANSWERS ABOUT THE SPECIAL MEETING

AND THE PROPOSALS

The following questions and answers address briefly some questions you may have regarding the Special Meeting and the Proposals (as defined below). These questions and answers may not address all questions that may be important to you as a stockholder of the Company. Please refer to the more detailed information contained elsewhere in this proxy statement and the documents referred to or incorporated by reference in this proxy statement.

Q:Why did I receive these proxy materials?

A:         We are providing these proxy materials in connection with the solicitation by our Board of Directors of proxies to be voted at the Special Meeting in connection with the issuancedate. Each share of common stock upon the conversion of our Convertible Notes (as defined below).

On August 16, 2017, the Company completed the offering (the “Offering”) of $125,000,000 aggregate principal amount of 5.875% convertible senior notes due 2037 (the “Convertible Notes”) in a private placement transaction pursuantentitles you to Rule 144A under the Securities Act of 1933, as amended (the “Securities Act”), with Citigroup Global Markets Inc., as the initial purchaser (the “Initial Purchaser”). On September 7, 2017, the Company completed a private placement of an additional $11,750,000 aggregate principal amount of the Convertible Notes to the Initial Purchaser. The total net proceeds from the offering, after deducting discounts, commissions and estimated offering expenses payable by the Company, were approximately $132.0 million. The Company utilized approximately $40 million of the proceeds to repurchase shares of the Company’s common stock. The Company intends to use the remainder of the net proceeds from the Offering to finance the cash portion of the acquisition of NBIC Holdings, Inc., the parent company of Narragansett Bay Insurance Company, which is expected to close as early as the fourth quarter of 2017.

The conversion of all of the outstanding Convertible Notes into common stock would result in the issuance of more than 20% of the Company’s voting power and shares of common stock outstanding prior to such issuance which, as described below, requires stockholder approval under the rules of the NYSE. Accordingly, the Convertible Notes currently are convertible only into cash unless and until stockholder approval is obtained.

Because the Company’s common stock is listed on the NYSE, the Company is subject to the NYSE’s rules and regulations. NYSE Rule 312.03(c) requires stockholder approval prior to the issuance of common stock, or securities convertible into or exercisable for common stock, in any transaction or series of transactions if (i) the common stock to be issued has, or will have upon issuance, voting

power equal to or in excess of 20% of the voting power outstanding before the issuance of such stock or of securities convertible into or exercisable for common stock, or (ii) the number of shares of common stock to be issued is, or will be upon issuance, equal to or in excess of 20% of the number of shares of common stock outstanding before the issuance of the common stock or of securities convertible into or exercisable for common stock (the “Issuance Proposal”).

At the Special Meeting, in accordance with NYSE Rule 312.03(c), you will be asked to consider andone vote on a proposal to approve the Issuance Proposal.

Unless and until the Issuance Proposal is approved by the Company’s stockholders, the conversion option that is part of the Convertible Notes will be accounted for as a derivative liability pursuant to accounting standards relating to derivative instruments and hedging activities (notwithstanding other factors to be evaluated by the Company each reporting period regarding the classification of derivative instruments).

For each financial statement period after issuance of the Convertible Notes, a hedge gain (or loss) will be reported in the Company’s income statement to the extent the valuation of the derivative liability changes from the previous period as a result of changes in the market price of the Company’s common stock or changes in other valuation inputs and assumptions. For example, if the stock price increases, the value of the option increases and there would be a hedge loss reported in the period. This could result in significant fluctuations in the Company’s consolidated statement of comprehensive income (loss) from period to period and have a material adverse effect on the Company’s earnings per share. In addition, if the Company is required to settle its obligations in respect of the Convertible Notes solely in cash, the Company’s cash flow and liquidity position could be adversely impacted.

Our Board of Directors believes that the Issuance Proposal is in the best interests of the Company and its stockholders and, therefore, recommends that you vote “FOR” the Issuance Proposal.

Q:What items of business will be voted on at the Special Meeting?

A:         The business expecteditem to be voted on at the Special Meeting is considering approval of the following proposals:

To consider and vote on a proposal to approve, as required pursuant to NYSE Rule 312.03(c), the Issuance Proposal;

To consider and vote on the Adjournment Proposal, as necessary and appropriate; and

To consider and transact such other business as may properly come before the Special Meeting and any adjournments or postponements thereof.

To be properly brought before the Special Meeting, any additional items of business must be presented in accordance with applicable law and the Company’s by-laws. If businessannual meeting. Cumulative voting is not properly brought beforepermitted. On the Special Meeting, there will not be an opportunity to discuss any such matters at the Special Meeting.

Q:Where and when is the Special Meeting?

A:         The Special Meeting will be held at 2600 McCormick Drive, Suite 300, Clearwater, Florida 33759 on December 1, 2017 at 10:00 a.m., Eastern Time.

Q:Who can attend and vote at the Special Meeting?

A:         You are entitled to receive notice of and to attend and vote at the Special Meeting, or any postponement or adjournment thereof, if, as of the close of business on October 16, 2017, the Record Date, you were a holder of record of our common stock.

As of the Record Date, there were 24,400,174 outstandingdate, 26,569,804 shares of our common stock each of which is entitled to one vote on each matter to come before the Special Meeting.

If you wish to attend the Special Meeting and your shares are held in an account at a broker, dealer, commercial bank, trust company, or other nominee (i.e., in “street name”), you willwere outstanding. We need to bring a copy of your voting instruction card or statement reflecting your share ownership as of the Record Date. “Street name” holders who wish to vote at the Special Meeting will need to obtain a proxy from the broker, dealer, commercial bank, trust company, or other nominee that holds their shares.

Q:What do I need to bring in order to attend the Special Meeting?

A:         You will need to bring the admission ticket mailed to you with this proxy statement and a form of personal photo identification in order to be admitted to the Special Meeting.

Q:How many shares must be present to conduct business at the Special Meeting?

A:         A quorum is necessary to hold a valid meeting of stockholders. For each of the Proposals to be presented at the Special Meeting, the holders of a majority of shares of our common stock outstanding on the Record Date, must be present at the Special Meeting, in person or by proxy. If you vote—including by Internet, telephone or proxy card—your shares voted will be counted towards the quorum for the Special Meeting. Abstentions are counted as present for the purpose of determining a quorum; broker non-votes are not counted for the purpose of determining the presence of a quorum at the Special Meeting as the Proposals to be considered would not be evaluated as routine by the NYSE.

Q:What are my voting choices?

A:         You may vote “FOR” or “AGAINST” or you may “ABSTAIN” from voting on any Proposal to be voted on at the Special Meeting. Your shares will be voted as you specifically instruct. If you sign your proxy or voting instruction card without giving specific instructions, your shares will be voted in accordance with the recommendations of our Board of Directors and in the discretion of the proxy holders on any other matters that properly come before the meeting. If you return your proxy card and “ABSTAIN” from voting, it will have the same effect as a vote against the Issuance Proposal and the Adjournment Proposal.

Q:What vote is required to approve the Proposals?

A:         The Issuance Proposal requires the affirmative vote of a majority of the shares of our common stock outstanding on the record date, represented in person or by proxy, to hold the annual meeting.

ConfidentialVoting. Your vote is confidential and will not be disclosed to any officer, director or employee, except in certain limited circumstances, such as when you request or consent to disclosure.

VotebyProxy. If your shares of common stock are held in your name, you can vote your shares on items presented at the annual meeting or by proxy. There are three ways to vote by proxy:

1.By Telephone — Stockholders can vote by telephone by calling1-800-652-VOTE (8683) and following the instructions on the proxy card;

2.By Internet — You can vote over the Internet atwww.edocumentview.com/HRTG by following the instructions on the proxy card; or

3.By Mail — You can vote by mail by signing, dating and mailing a proxy card that you request in writing.

SubmittingVotingInstructionsforSharesHeldThroughaBroker. If your shares are held in a stock brokerage account or by a bank or other nominee, you are considered the beneficial owner of shares held in “street name,” and your broker, bank or nominee is considered the stockholder of record with respect to those shares. As the beneficial owner, you have the right to direct your broker, bank or nominee on how to vote and are also invited to attend the annual meeting with proper evidence of stock holdings, such as a recent brokerage account or bank statement. Street name stockholders should check the voting thereoninstruction cards used by their brokers or nominees for specific instructions on methods of voting. If your shares are held in street name, you must contact your broker or nominee to revoke your proxy.

If you hold shares through a broker, follow the voting instructions you receive from your broker. If you want to vote in person at the annual meeting, you must obtain a legal proxy from your broker and present it at the annual meeting. If you do not submit voting instructions to your broker, your broker may still be permitted to vote your shares in certain cases. Brokers may vote your shares as described below.

Non-discretionaryItems. Allitems,otherthantheratificationoftheappointmentoftheCompany’sindependentregisteredpublicaccountingfirm,are“non-discretionary”items.Itiscriticallyimportantthatyousubmityourvotinginstructionsifyouwantyoursharestocountfornon-discretionaryitems,suchastheelectionofdirectors. Your shares will remain unvoted for such items if your broker does not receive instructions from you.

DiscretionaryItem. The ratification of the appointment of the Company’s independent registered public accounting firm is a “discretionary” item. Brokers that do not receive instructions from beneficial owners may vote uninstructed shares in their discretion.

In order to carry on the business of the meeting, we must have a quorum. This means that stockholders representing a majority of the common stock issued and outstanding as of the record date must be present at whichthe annual meeting, either in person or by proxy, for there to be a quorum is present. Under applicable NYSE rules, abstentionsat the annual meeting. Abstentions and brokernon-votes are counted as present for purposes of determining a quorum and are also counted as shares voted with respect to such proposal, and therefore, if you return your proxy card and “ABSTAIN” from voting, it will have the same effect as a vote against the Issuance Proposal. The Adjournment Proposal requires the affirmative vote of a majority of the shares of our common stock present and entitled to vote at the Special Meeting, whether or not a quorum is present.

Q:How many shares of common stock are issuable upon conversion of the Convertible Notes?

A:         Upon conversion of all of the Convertible Notes, the Company would issue approximately 9,165,860 shares of common stock, representing approximately 37.6% of the total outstanding shares as of the Record Date, assuming (i) the Company elects to settle all conversions entirely in shares of common stock and (ii) such conversions occur at the initial conversion rate of 67.0264 shares of common stock per $1,000 principal amount of Convertible Notes.

Q:What will happen if the Issuance Proposal is not approved?

A:         If the Issuance Proposal is not approved prior to the relevant conversion date, the Company will be required to pay to holders in respect of each $1,000 principal amount of Convertible Notes being converted solely an amount in cash as if the Company had elected a “cash settlement”.

Unless and until the Issuance Proposal is approved by the Company’s stockholders, the conversion option that is part of the Convertible Notes will be accounted for as a derivative liability pursuant to accounting standards relating to derivative instruments and hedging activities (notwithstanding other factors to be evaluated by the Company each reporting period regarding the classification of derivative instruments).

For each financial statement period after issuance of the Convertible Notes, a hedge gain (or loss) will be reported in the Company’s income statement to the extent the valuation of the derivative liability changes from the previous period as a result of changes in the market price of the Company’s common stock or changes in other valuation inputs and assumptions. For example, if the stock price increases, the value of the option increases and there would be a hedge loss reported in the period. This could result in significant fluctuations in the Company’s consolidated statements of income (loss) and comprehensive income (loss) from period to period and have a material adverse effect on the Company’s earnings per share. In addition, if the Company is required to settle its obligations in respect of the Convertible Notes solely in cash, the Company’s cash flow and liquidity position could be adversely impacted.

Whether the Issuance Proposal is approved at the Special Meeting will have no effect on the acquisition of NBIC Holdings, Inc.

Q:How does the Company’s Board of Directors recommend that I vote?

A:         Our Board of Directors, after careful consideration, unanimously recommends that our stockholders vote“FOR” the approval of the Issuance Proposal and“FOR” the Adjournment Proposal.

Q:How will our directors and executive officers vote on the Proposals?

A:         Our directors and current executive officers have informed us that, as of the date of this proxy statement, they intend to vote all of their shares of our common stock in favor of the approval of each of the Proposals. As of the Record Date, excluding any shares issuable upon the exercise of currently outstanding options, our directors and current executive officers owned, in the aggregate, shares of our common stock, representing collectively approximately 14.6% of the votes eligible to be cast at the Special Meeting.

Q:What do I need to do now?

A:         We urge you to read this proxy statement carefully and to consider how approving the Proposals affects you. Then simply mail your completed, dated and signed proxy card in the enclosed return envelope as soon as possible so that your shares can be voted at the Special Meeting of our stockholders. Holders of record may also vote by telephone or the Internet by following the instructions on the proxy card.

Q:What happens if I do not respond or if I respond and fail to indicate my voting preference or if I abstain from voting?

A:         If you fail to sign, date, and return your proxy card or fail to vote by telephone or Internet as provided on your proxy card, your shares will not be counted towards establishing a quorum but brokernon-votes are not considered “present” for the Special Meeting, which requires holders representing a majoritypurposes of the outstanding shares of our common stock to be present in person or by proxy. If you respond and do not indicate your voting preference, we will count your proxy as a vote in favor of the approval of each of the Proposals.

Q:If my shares are held in “street name” by my broker, dealer, commercial bank, trust company, or other nominee, will such broker or other nominee vote my shares for me?

A:         You should instruct youronnon-discretionary items. A broker or other nominee on how to vote your shares using the instructions provided by such broker or other nominee. Absent specific voting instructions, brokers or other nominees who hold shares of Company common stock in “street name” for customers are prevented by the NYSE Rules from exercising voting discretion in respect of non-routine or contested matters. The Company expects thatnon-vote occurs when the NYSE evaluates the Proposals to be voted on at the Special Meeting to determine whether each Proposal is a routine or non-routine matter, the Proposals would not be evaluated as routine. Shares not voted by a broker or other nominee holding shares for a beneficial owner does not vote on a particular proposal because suchthe broker or other nominee does not have instructions or cannot exercise discretionary voting power with respect to one or more Proposals are referred to as “broker non-votes”. Such broker non-votes mayand has not be counted for the purpose of determining the presence of a quorum at the Special Meeting in the absence of a routine proposal. It is important that you instruct your broker or other nominee on how to vote your shares of Company common stock held in “street name” in accordance with the votingreceived instructions provided by such broker or other nominee.

Q:How do I vote?

A:         If you are aregistered stockholder (i.e., you hold your shares in your own name through our transfer agent, Computershare Investor Services, and not through a broker, bank, or other nominee that holds shares for your account in “street name”), you may vote by proxy via the Internet, by telephone, or by mail by following the instructions provided on the proxy card. Proxies submitted by telephone or through the Internet must be received by 11:59 p.m., Eastern Time, on November 30, 2017. Please see the proxy card provided to you for instructions on how to submit your proxy by telephone or the Internet. Stockholders of record who attend the Special Meeting may vote in person by obtaining a ballot from the inspector of elections.beneficial owner.

If you are abeneficial owner of shares (i.e.,RevokingYourProxy. You can revoke your shares are held in the name of a brokerage firm, bank or a trustee), you may vote by proxy by following the instructions provided in the vote instruction form or other materials provided to you by the brokerage firm, bank, or other nominee that holds your shares. To vote in person at the Special Meeting, you must obtain a legal proxy from the brokerage firm, bank, or other nominee that holds your shares.

Q:Can I change my vote after I have mailed my proxy card?

A:         Yes. Whether you attend the Special Meeting or not, any proxy given pursuant to this solicitation may be revoked by the person giving it at any time before it is voted. A proxy may be revoked in writingyour shares are voted by (1) delivering a written revocation notice prior to the Company’s Corporate Secretary, at or before taking of the vote at the Special Meeting. A written notice of revocation or a duly executed proxy, in either case later dated than the prior proxy relatingannual meeting to the same shares, will be treated as the final vote.

A proxy may also be revoked by attending the Special Meeting and voting in person, although attendance at the Special Meeting will not itself revoke a proxy. Any written notice of revocation or subsequent proxy should be sent so as to be delivered to Steven Martindale,Kirk Lusk, Chief Financial Officer, and Secretary, Heritage Insurance Holdings, Inc., 2600 McCormick Drive, Suite 300, Clearwater, Florida 33759,33759; (2) submitting a later-dated proxy that we receive no later than the conclusion of voting at the annual meeting; or hand delivered to Steven Martindale,(3) voting in person at or before the takingannual meeting. Attending the annual meeting does not revoke your proxy unless you vote in person at the meeting.

VotesRequiredtoElectDirectors. Directors will be elected by a plurality of the votevotes present in person or by proxy at the Special Meeting.annual meeting and entitled to vote. A “plurality” means that the individuals who receive the largest number of votes are elected as directors up to the maximum number of directors to be elected at the annual meeting. The size of the Board is currently set at ten members.

If you holdVotesRequiredtoAdoptOtherProposals. The ratification of Grant Thornton LLP’s appointment as independent registered public accounting firm requires the affirmative vote of a majority of the shares of common stock represented at the annual meeting and entitled to vote thereon.

“Withhold” Votes, “Abstentions”and“BrokerNon-Votes.” You may “withhold” your shares throughvote with respect to any nominee in the election of directors and may “abstain” from voting on the other proposals. Shares “abstaining” from voting on any proposal will be counted as present at the annual meeting for purposes of establishing the presence of a broker, dealer, commercial bank, trust company, or otherquorum. “Withhold” votes with respect to any nominee you should follow the instructions of such broker or other nominee regarding revocation of proxies.

Q:Am I entitled to appraisal rights?

A:         No. Youfor director will have no right under Delaware law to seek appraisaleffect on the election of your sharesdirectors. Your abstention will have the effect of our common stock in connection witha vote against the Proposals.

Q:Where can I find the resultsratification of the voting?

A:         We intend to announce preliminary voting results at the Special Meeting andappointment of Grant Thornton LLP as independent registered public accounting firm for fiscal year 2018. Brokernon-votes will publish final results through a Current Reporthave no effect on Form 8-K to be filed with the U.S. Securities and Exchange Commission (“SEC”) within four business days after the Special Meeting. The Current Report on Form 8-Kelection of directors. There will be available onno brokernon-votes with respect to the Internet at our website, http://investors.heritagepci.com/sec-filings.ratification of Grant Thornton LLP’s appointment as independent registered public accounting firm, as it is a discretionary item.

JOBS Act Explanatory Note

Q:Who will pay for the cost of soliciting proxies?

A:         The Company is paying the costsWe are an “emerging growth company” under applicable federal securities laws and are therefore permitted to take advantage of the solicitation of proxies. The Company has retained Georgeson LLC to assist in obtaining proxies by mail, facsimile, telephone or email from brokerage firms, banks, broker-dealers or other similar organizations representing beneficial owners of shares for the Special Meeting. The Company has agreed to pay such firm a fee of approximately $15,000.00 plus out-of-pocket expenses. Georgeson LLC may be contacted toll-free at 1-877-278-9670. The Company may also reimburse brokerage firms, banks, broker-dealers or other similar organizations for the cost of forwarding proxy materials to beneficial owners. In addition, certain of the Company’s directors, officers and regular employees, without additional compensation, may solicit proxies on the Company’s behalf in person, by telephone, by fax or by electronic mail. See “Proxy Solicitation and Costs”reduced public company reporting requirements. As an emerging growth company, we provide in this proxy statement for further information.

Q:What is “householding” and how does it affect me?

A:         The SEC has adoptedthe scaled disclosure permitted under the Jumpstart Our Business Startups Act of 2012 (the “JOBS Act”), including the compensation disclosures required of a “smaller reporting company,” as that term is defined in Rule12b-2 promulgated under the Securities Exchange Act of 1934, as amended (the “Exchange Act”). In addition, as an emerging growth company, we are not required to conduct votes seeking approval, on an advisory basis, of the compensation of our named executive officers or the frequency with which such votes must be conducted. We will remain an “emerging growth company” until the earliest of (i) the last day of the fiscal year in which we have total annual gross revenues of $1.07 billion or more; (ii) December 31, 2019; (iii) the date on which we have issued more than $1 billion in nonconvertible debt during the previous three years; or (iv) the date on which we are deemed to be a large accelerated filer under the rules that permit companies and intermediaries, such as brokers, to satisfyof the delivery requirements for proxy statements 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.SEC.

If you receive notice from your broker that itPROPOSALS TO BE VOTED ON

Proposal 1: Election of Directors

Nominees

The size of the Board is currently set at ten members. At the annual meeting, the stockholders will elect ten directors to serve until the 2019 annual meeting of stockholders or until their respective successors are elected and qualified. Any director vacancy occurring after the election may be filled by a majority vote of the remaining directors. In accordance with the Company’s Bylaws, a director appointed to fill a vacancy will be householding communicationsappointed to your address, householdingserve until the next annual meeting of stockholders.

Assuming a quorum is present, the ten nominees receiving the highest number of affirmative votes of shares entitled to be voted for them will continue until yoube elected as directors of the Company. Stockholders are notified otherwisenot entitled to cumulate votes in the election of directors. All nominees have consented to serve as directors, if elected. If any nominee is unable or until you revoke your consent. If,unwilling to serve as a director at the time of the annual meeting, the persons who are designated as proxies intend to vote, in their discretion, for such other persons, if any, time, you no longer wish to participate in householding and would prefer to receive a separate proxy statement, please notify your broker directly or direct your written request to: Steven Martindale, Chief Financial Officer and Secretary, Heritage Insurance Holdings, Inc., 2600 McCormick Drive, Suite 300, Clearwater, Florida 33759, oras may be designated by phone at (727) 362-7200.

Q:Can I obtain an electronic copythe Board. As of the date of proxy material?

A:         Yes, this proxy statement, the accompanying noticeBoard has no reason to believe that any of Special Meetingthe director nominees named herein will be unable or unwilling to serve as a director if elected.

The Company believes that its Board, as a whole, should encompass a range of talent, skill, diversity, experience and expertise enabling it to provide sound guidance with respect to the Company’s operations and interests. In addition to considering a candidate’s background, experience and accomplishments, candidates are reviewed in the context of the current composition of the Board and the proxy cardevolving needs of our business. Although the Company does not have a formal policy with regard to the consideration of diversity in identifying candidates, the Corporate Governance and Nominating Committee strives to nominate candidates with a variety of complementary skills so that, as a group, the Board will possess the appropriate level of talent, skills and expertise to oversee the Company’s business. The Company regularly assesses the size of the Board, whether any vacancies are availableexpected due to retirement or otherwise, and the need for particular expertise on the InternetBoard. The Company’s policy is to have atwww.investorvote.com/HRTG. least a majority of our directors qualify as “independent directors” as defined in the rules of the NYSE. Currently, seven of our ten directors are independent.

The Corporate Governance and Nominating Committee seeks candidates with strong reputations and experience in areas relevant to the strategy and operations of the Company, particularly in industries and growth segments that the Company serves, as well as key geographic markets where it operates. Each of the director nominees holds or has held senior positions in complex organizations and has operating experience that meets this objective, as described below. In these positions, they have also gained experience in core management skills, such as strategic and financial planning, financial reporting, corporate governance, risk management and leadership development.

The Corporate Governance and Nominating Committee also believes that each of the nominees, each of whom is a current director, has the experience, expertise, integrity, sound judgment and ability to engage management in a collaborative fashion to collectively comprise an effective Board. In addition, the Corporate Governance and Nominating Committee believes that each of the nominees is committed to devoting significant time and energy to service on the Board and its committees.

The names of the director nominees, their ages as of April 24, 2018, their recent employment or principal occupation, the names of any public companies for which they currently serve as a director or have served as a director within the past five years, and their period of service as a Company director are set forth below.

 

Q:What happens if the Special Meeting is adjourned or postponed?

Name

Age

Position

Bruce Lucas

46Chairman and CEO

Richard Widdicombe

59President and Director

Pete Apostolou

43Director

Irini Barlas(1)(2)

46Director

Trifon Houvardas(1)

51Director

Steven Martindale

55Director

James Masiello(2)(3)

77Director

Nicholas Pappas(2)(3)

43Director

Joseph Vattamattam

41Director

Vijay Walvekar(1)(3)

71Director

A:         Although it

(1)Current member of our Audit Committee.

(2)Current member of our Compensation Committee.
(3)Current member of our Corporate Governance and Nominating Committee.

DIRECTOR NOMINEES

BruceLucas. Bruce Lucas has served as our Chairman and CEO since May 2014. Mr. Lucas served as our Chairman and Chief Investment Officer from August 2012 to May 2014. Prior to joining the Company, from January 2012 to August 2012, Mr. Lucas served as the Managing Member of IIM Holdings, II, LLC, an investment company. Prior to that, Mr. Lucas served as Chief Executive Officer of Infinity Investment Funds, a hedge fund, from April 2009 to December 2011. Prior to joining Infinity, Mr. Lucas was a restructuring attorney at Weil, Gotshal & Manges LLP. Mr. Lucas brings to the board of directors a critical link to management’s perspective in board discussions regarding the business and strategic direction of the Company.

RichardWiddicombe. Mr. Widdicombe has served as our President since August 2012 and served as our Chief Executive Officer from August 2012 to May 2014. Prior to joining the Company, Mr. Widdicombe served as Risk Manager of Homeowners Choice Property & Casualty Insurance Company (NYSE: HCI) from November 2009 to September 2011. Prior to that, Mr. Widdicombe served as President of People’s Trust Insurance Company from July 2007 to February 2009. Mr. Widdicombe brings to the board of directors anin-depth knowledge of the insurance industry gained from his years of leadership experience at multiple insurance carriers.

PeteApostolou. Mr. Apostolou has served on our board of directors since August 2012. Mr. Apostolou is the owner of Central Parking Services, which he founded in 2010. He is also a real estate broker and owner of Alexa Realty of St. Petersburg, which he founded in 2004. Mr. Apostolou also serves as a manager and owner of several other commercial real estate companies. Mr. Apostolou brings to the board of directors anin-depth knowledge of the Florida commercial and residential real estate market.

IriniBarlas. Ms. Barlas has served on our board of directors since August 2014. Ms. Barlas is the Chief Financial and Operating Officer of Megastar Advisors, LLC, an insurance marketing and training organization, and has served in such role since January 2014. Since February 2010, Ms. Barlas has also served as the Director of Accounting and Finance of Barlas & Chambers, a provider of tax, insurance and investment services. Previously, from January 2009 through January 2010, Ms. Barlas was an auditor at Grant Thornton LLP. Ms. Barlas is a member of the American Institute of Certified Public Accountants and the Florida Institute of Certified Public Accountants. Ms. Barlas brings to the board of directors extensive experience in financial statement preparation and financial reporting and analysis.

TrifonHouvardas. Mr. Houvardas has served on our board of directors since August 2012. Mr. Houvardas has been involved in the real estate industry since 1992 and currently manages all aspects of three real estate businesses, Foresight Property Services, Foresight Holding Inc. and Fasco Investments Inc. Mr. Houvardas serves as a director of First Home Bank, LLC and Atlas FinTech Holdings Corporation. Mr. Houvardas possesses particular knowledge and experience in real estate and complex transactions that strengthen the board’s collective qualifications, skills and experience.

Steven Martindale. Mr. Martindale has served on our board of directors since January 2018. Mr. Martindale served as our Chief Financial Officer from May 2016 to January 2018 and as ourCo-Chief Financial Officer from January 2018 to April 2018. Prior to joining the Company, Mr. Martindale served as Chief Financial Officer at People’s Trust Insurance Company, a privately held insurer licensed in the State of Florida, from September 2013 to May 2016. Prior to People’s Trust, Mr. Martindale was Chief Regulatory Officer for the State of Ohio from April 2011 to September 2013 and was responsible for leading the Offices of Risk Assessment, Product Regulation and Actuarial Services and Fraud, Enforcement and Licensing. From August 2008 to September 2013, Mr. Martindale was a partner and consulting chief financial officer for Focus CFO, a consultancy providing financial expertise and services on a permanent part-time basis to help clients navigate financial adjustments and growth. From January 2005 to August 2008, Mr. Martindale worked at ProCentury as Vice President Corporate Governance, assisting in the development of project management processes and the implementation of Sarbanes-Oxley compliance measures. Mr. Martindale has also held various other positions in both accounting and auditing. Mr. Martindale brings to the boardin-depth financial knowledge, as well as executive management and leadership experience.

JamesMasiello. Mr. Masiello has served on our board of directors since April 2014 and served as a director pending regulatory approval in 2013. Mr. Masiello founded Alliance Holdings, Inc., the parent company of Strategic Independent Agency Alliance, Inc. (SIAA), a national alliance of insurance agents, in 1994 and has served as its Chairman and Chief Executive Officer since that time. Mr. Masiello brings to the board of directors extensive operational and executive leadership experience in the insurance industry.

NicholasPappas. Mr. Pappas has served on our board of directors since April 2014 and served as a director pending regulatory approval in 2013. Mr. Pappas is the President and owner of FlameStone American Grill, a restaurant in the Tampa area that opened in 2007. Mr. Pappas also owns or serves on the executive team of several commercial real estate holding companies with properties in the Tampa and Jacksonville, Florida areas. Mr. Pappas brings to the board of directors an entrepreneurial and executive management background, as well as a strong knowledge of the Florida commercial real estate market.

JosephVattamattam. Mr. Vattamattam has served on our board of directors since April 2014 and served as a director pending regulatory approval in 2013. Mr. Vattamattam is the Chief Executive Officer of HealthMap Solutions, a provider of technology and consulting services to healthcare organizations, a position he has held since July 2013. Prior to that, Mr. Vattamattam served as Vice President of Medical Economics at CareCentrix, Inc., a provider of home health solutions, from August 2010 to July 2013 and as Area Vice President, Operations from January 2010 to August 2010. Prior to that, Mr. Vattamattam held several positions at WellCare Health Plans, a provider of managed care services, from June 2007 to December 2009, most recently as Director, Health Services. Mr. Vattamattam previously held positions at Wachovia Securities and PricewaterhouseCoopers LLP. Mr. Vattamattam brings to the board executive management and leadership skills, as well as anin-depth knowledge of capital markets and financial analysis.

VijayWalvekar. Mr. Walvekar has served on our board of directors since August 2012. Mr. Walvekar currently serves as Vice President of Central Home Health Care, Inc., a position he has held since January 1985. Mr. Walvekar also serves as President or Managing Member of several real property holding companies owning real estate in Florida and Michigan. Mr. Walvekar also serves as Managing Director of Control-Touch Electronics (Poona) Pvt. Ltd., an Indian technology company. Mr. Walvekar possesses knowledge and experience in real estate, strategic planning and leadership.

Required Vote

Directors are elected by a plurality of the votes of the shares present in person or by proxy at the annual meeting and entitled to vote on the election of directors. The individuals who receive the largest number of votes will be elected as directors up to the maximum number of directors to be elected at the annual meeting.

Recommendation of the Board of Directors

THE BOARD RECOMMENDS A VOTE “FOR” THE ELECTION OF ALL NOMINEES NAMED ABOVE.

Proposal 2: Ratification of Appointment of Independent Registered Public Accounting Firm

Grant Thornton LLP has served as the Company’s independent registered public accounting firm since November 2013 and has been appointed by the Audit Committee to continue as the Company’s independent registered public accounting firm for the fiscal year ending December 31, 2018. In the event that ratification of this selection is not expected,approved by the Special Meeting may be adjourned or postponed for the purpose of soliciting additional proxies. Any adjournment or postponement may be made without notice, other than by an announcement made at the Special Meeting, by approvalaffirmative vote of the holders of a majority of the outstanding shares of ourcommon stock of the Company represented at the annual meeting in person or by proxy and entitled to vote on the item, the Audit Committee and the Board of Directors will review the Audit Committee’s future selection of an independent registered public accounting firm.

Representatives of Grant Thornton LLP will be available at the annual meeting. The representatives will have an opportunity to make a statement and will be available to respond to appropriate questions.

Required Vote

The affirmative vote of the holders of a majority of the Company’s common stock present at the annual meeting in person or represented by proxy and entitled to vote on this proposal is required to approve the ratification of the appointment of Grant Thornton LLP as the Company’s independent registered public accounting firm for the current fiscal year.

Recommendation of the Board of Directors

THE BOARD RECOMMENDS A VOTE “FOR” RATIFICATION OF THE APPOINTMENT OF GRANT THORNTON LLP AS THE COMPANY’S INDEPENDENT REGISTERED PUBLIC ACCOUNTING FIRM FOR THE FISCAL YEAR ENDING DECEMBER  31, 2018.

BOARD OF DIRECTORS AND CORPORATE GOVERNANCE

Board Leadership Structure

The Board determines whether it is appropriate to combine or separate the roles of Chairman of the Board and CEO depending on the Company’s circumstances at the Special Meeting,time. Our Board of Directors currently believes it is in the best interests of the

company to combine the positions of Chairman and CEO because this provides the Company with unified leadership and direction. Mr. Lucas, who currently serves as the Company’s CEO and as Chairman of the Board, possessesin-depth knowledge of the issues, opportunities and challenges the Company faces, and is thus best positioned to develop agendas and highlight issues that ensure that the Board’s time and attention are focused on the most critical matters. In addition, the Board has determined that this leadership structure is optimal because it believes that having one leader serving as both the Chairman and CEO provides decisive, consistent and effective leadership, as well as clear accountability. Having one person serve as Chairman and CEO also enhances the Company’s ability to communicate its message and strategy clearly and consistently to its stockholders, employees, and business partners, particularly during times of turbulent economic and industry conditions. Although the Board believes that the combination of the Chairman and CEO roles is appropriate under current circumstances, it will continue to review this issue periodically to determine whether, based on the relevant facts and circumstances, separation of these offices would serve the Company’s best interests and the best interests of its stockholders.

Board of Directors Role in Risk Oversight

Our Board oversees the risk management activities designed and implemented by our management. The Board executes its oversight responsibility for risk management both directly and through its committees. The full Board also considers specific risk topics, including risks associated with our strategic plan, business operations and capital structure. In addition, the Board receives detailed regular reports from members of our senior management and other personnel that include assessments and potential mitigation of the risks and exposures involved with their respective areas of responsibility.

Our Board has delegated to the Audit Committee oversight of our risk management process. Our other Board committees also consider and address risk as they perform their respective committee responsibilities. All committees report to the full Board as appropriate, including when a matter rises to the level of a material or notenterprise level risk. The independent Board members also discuss the Company’s significant risks when they meet in executive session without management, as described below.

Meetings and Committees of the Board of Directors

During 2017, the Board held five meetings. During 2017, each director attended at least 75% of the aggregate of the total number of meetings of the Board held during the period in which he or she was a quorum exists. Any signed proxies receiveddirector and the total number of meetings held by all of the committees of the Board on which he or she served. The Board has an Audit Committee, a Compensation Committee and a Corporate Governance and Nominating Committee. The Audit, Compensation and Corporate Governance and Nominating Committees were formally established in May 2014 in connection with the Company’s initial public offering and operate under written charters adopted by the Company will be voted in favor of an adjournment or postponement in these circumstances. Any adjournment or postponementBoard.

At the Board meetings, independent directors of the Special MeetingCompany meet regularly in executive session without management as required by the NYSE listing standards. Generally, executive sessions are held in conjunction with regularly-scheduled meetings of the Board. Mr. Masiello presides over executive sessions of the Board. In 2017, thenon-employee independent members of the Board met in executive session five times.

AuditCommittee. Ms. Barlas and Messrs. Houvardas and Walvekar serve on the Audit Committee. Ms. Barlas serves as the chairwoman of our Audit Committee and, subject to herre-election to serve an additionalone-year term, the Board has elected Ms. Barlas to continue as chairwoman of the Audit Committee. The Audit Committee is composed ofnon-employee directors, each of whom is independent under rule10A-3 under the Exchange Act and the applicable listing standards of the NYSE, and is responsible for, among other things, supervising internal audit and reviewing internal financial controls and accounting principles to be employed in the purposepreparation and review of solicitingour financial statements. In addition, the Audit Committee has authority to engage public accountants to audit our annual financial statements and determine the scope of the audit to be undertaken by such accountants. Ms. Barlas is our audit committee financial expert under the SEC rule implementing Section 404 of the Sarbanes-Oxley Act of 2002. During 2017, the Audit Committee held four meetings.

CompensationCommittee. Messrs. Masiello and Pappas and Ms. Barlas serve on the Compensation Committee. Mr. Masiello serves as the chairman of our Compensation Committee and, subject to hisre-election to serve an additional proxies will allow Company stockholders who have already sent in their proxiesone-year term, the Board has elected Mr. Masiello to revoke them at any time priorcontinue as chairman of the Compensation Committee. The Compensation Committee is composed ofnon-employee directors, each of whom is independent as required by the applicable listing standards of the NYSE, and is responsible for, among other things, reviewing and approving compensation of our CEO and our other executive officers. Additionally, the Compensation Committee reviews and recommends to their use.

Q:Who can help answer my other questions?

A:         If you have more questions aboutour CEO and the Proposals or voting, you should contact Investor Relations,Board policies, practices and procedures relating to the compensation of managerial employees and the establishment and administration of certain employee benefit plans for managerial employees. The Compensation Committee has the authority to administer the Heritage Insurance Holdings, Inc. Omnibus Incentive Plan (our “Omnibus Incentive Plan”), and to advise and consult with our officers regarding managerial personnel policies. During 2017, the Compensation Committee held two meetings.

CorporateGovernanceandNominatingCommittee. Messrs. Masiello, Pappas and Walvekar serve on the Corporate Governance and Nominating Committee. Mr. Pappas serves as the chairman of our Corporate Governance and Nominating Committee and, subject to hisre-election to serve an additionalone-year term, the Board has elected Mr. Pappas to continue as chairman of the Corporate Governance and Nominating Committee. The Corporate Governance and Nominating Committee is composed of independentnon-employee directors, each of whom is independent as required by the applicable listing standards of the NYSE, and is responsible for, among other things, assisting the Board with its responsibilities regarding:

the identification of individuals qualified to become directors;

the selection of the director nominees for the next annual meeting of stockholders;

the selection of director candidates to fill any vacancies on the Board;

the performance, composition, duties and responsibilities of the Board and the committees of the Board;

succession planning for our CEO; and

the operation of the Board with respect to corporate governance matters.

In evaluating and determining whether to nominate a candidate for a position on the Company’s Board, the Corporate Governance and Nominating Committee will consider the candidate’s professional ethics and values, relevant management experience and a commitment to enhancing stockholder value. The Company regularly assesses the size of the Board, whether any vacancies are expected due to retirement or otherwise, and the need for particular expertise on the Board. Candidates may come to the attention of the Corporate Governance and Nominating Committee from current Board members, stockholders, professional search firms, officers or other persons. The Corporate Governance and Nominating Committee will review all candidates in the same manner regardless of the source of recommendation. During 2017, the Corporate Governance and Nominating Committee held one meeting.

The Corporate Governance and Nominating Committee will consider stockholder recommendations of candidates when the recommendations are properly submitted in accordance with the Company’s Bylaws. Any stockholder recommendations which are submitted under the criteria summarized above should include the candidate’s name and qualifications for Board membership and should be addressed to one of our employees.

For purposes of potential nominees to be considered at the 2019 annual stockholders’ meeting, the Corporate Secretary must receive this information no earlier than February 22, 2019 and no later than the close of business on March 23, 2019 in accordance with the procedures in the Bylaws. The notice must set forth the candidate’s name, age, business address, residence address, principal occupation or employment, the number of shares beneficially owned by the candidate and information that would be required to solicit a proxy under federal securities law. In addition, the notice must include the stockholder’s name, address and the number of shares beneficially owned (and the period they have been held).

In 2017, the Company did not engage a third party to identify, evaluate or assist in identifying potential nominees for director.

Director Independence

There are no family relationships among any of the Company’s executive officers or directors. Our board of directors has affirmatively determined that each of Messrs. Apostolou, Houvardas, Masiello, Pappas, Vattamattam and Walvekar and Ms. Barlas is an “independent director,” as defined under the rules of the NYSE. In making the independence determination, the Board considered the current and prior relationships that eachnon-employee director has with the Company and all other facts and circumstances that the Board deemed relevant, including the beneficial ownership of the Company’s capital stock by eachnon-employee director and the transactions involving them as described in the section titled “Certain Relationships and Related Party Transactions.”

Governance Documents

The Company’s Audit Committee, Compensation Committee and Corporate Governance and Nominating Committee charters are available at www.heritagepci.com on the “Investor” page under the link “Corporate Governance.” In addition, the Board has adopted corporate governance guidelines, which are available at www.heritagepci.com on the “Investor” page under the link “Corporate Governance.” Information on, or accessible through, our website is not a part of, or incorporated by reference into, this proxy statement.

Communications with Directors

The Board has established a process to receive communications from stockholders. Stockholders and other interested parties may contact any member (or all members) of the Board, or thenon-management directors as a group, any Board committee or any

chair of any such committee by mail. To communicate with the Board, any individual directors or any group or committee of directors, correspondence should be addressed to the Board or any such individual directors or group or committee of directors by either name or title. All such correspondence should be sent c/o Kirk Lusk, Chief Financial Officer, Heritage Insurance Holdings, 2600 McCormick Drive, Suite 300, Clearwater, Florida 33759, telephone: (727) 362-720033759.

All communications received as set forth in the preceding paragraph will be opened by the Corporate Secretary for the sole purpose of determining whether the contents represent a message to our directors. The Corporate Secretary will forward copies of all correspondence that, in the opinion of the Corporate Secretary, deals with the functions of the Board or Georgeson LLC at 1 (877) 278-9670 (toll free).its committees or that he otherwise determines requires the attention of any member, group or committee of the Board.

ISSUANCE PROPOSAL—APPROVAL OF THE ISSUANCE OFAttendance at Annual Meeting

COMPANY COMMON STOCK UPON CONVERSION OFDirectors are encouraged, but not required, to attend our annual stockholders’ meeting. In 2017, seven directors attended the annual stockholders’ meeting.

THE CONVERTIBLE NOTESEXECUTIVE OFFICERS

On August 16, 2017,The names of the executive officers of the Company completedand their ages, titles and biographies are set forth below.

BruceLucas, 46, is being considered for the Offeringposition of $125,000,000 aggregate principal amountdirector of the Convertible Notes inCompany. See “Director Nominees” for a private placement transaction pursuant to Rule 144A underdiscussion of Mr. Lucas’ business experience.

RichardWiddicombe, 59, is being considered for the Securities Act, with the Initial Purchaser. On September 7, 2017, the Company completed a private placementposition of an additional $11,750,000 aggregate principal amountdirector of the Convertible NotesCompany. See “Director Nominees” for a discussion of Mr. Widdicombe’s business experience.

Kirk Lusk,56, has served as our Chief Financial Officer since April 2018 and as ourCo-Chief Financial Officer since January 2018. Prior to the Initial Purchaser. The total net proceedsjoining us, from the offering, after deducting discounts, commissions and estimated offering expenses payableJanuary 2013 to February 2018, Mr. Lusk served as Chief Financial Officer of Narragansett Bay Insurance Company (“NBIC”), which was acquired by the Company, were approximately $132.0 million. The Company utilized approximately $40 million of the proceeds to repurchase shares of the Company’s common stock. The Company intends to use the remainder of the net proceeds from the Offering to finance the cash portion ofus on November 30, 2017 in connection with the acquisition of NBIC Holdings, Inc., the parent company of NarragansettNBIC. Prior to that, Mr. Lusk served as International Chief Financial Officer of Aetna, Inc. from 2008 through 2012, Chief Financial Officer of Alea Group Holdings Bermuda Ltd. from 2005 through 2008 and Chief Financial Officer of GE ERC’s Global Casualty and GE Capital Auto Warranty Services from 1998 through 2004.

ErnieGarateix, 46, has served as our Chief Operating Officer since December 2014. Prior to that, from August 2012 to December 2014, Mr. Garateix served as our Executive Vice President. Prior to joining us, Mr. Garateix served as Vice President for American Integrity Insurance Group beginning in October 2007.

SharonBinnun, 56, has served as our Chief Accounting Officer since May 2016. Prior to that, she served as our Executive Vice President of Finance beginning in November 2014. Prior to joining us, Ms. Binnun served as the Executive Vice President of Cypress Property Insurance Company from July 2013 to August 2014. Prior to that, Ms. Binnun served as the Chief Financial Officer of Citizens Property Insurance Corporation from February 2007 to July 2013. Ms. Binnun’s prior employment includes Deputy Insurance Commissioner in Florida as well as a career at Deloitte & Touche. Ms. Binnun is a certified public accountant in the State of Florida.

JosephPeiso, 59, has served as our Vice President of Compliance since May 2014 and previously served as our Controller from September 2012 to May 2014. Prior to joining us, Mr. Peiso served as Chief Financial Officer of Sunz Insurance Holdings, LLC from September 2011 to August 2012. Prior to that, Mr. Peiso served as Chief Financial Officer of United Insurance Holdings Corporation (NASDAQ: UIHC) from January 2010 to August 2011. From June 2004 to December 2009, Mr. Peiso served as Managing Member of Sarasota Bay Insurance Company, whichManagers, LLC. Mr. Peiso is expected to close as early as the fourth quarter of 2017.

The conversion of all of the outstanding Convertible Notes into common stock would resulta certified public accountant in the issuanceState of more than 20% of the Company’s voting power and shares of common stock outstanding prior to such issuance which, as described below, requires stockholder approval under the rules of the NYSE. Accordingly, the Convertible Notes currently are convertible only into cash unless and until stockholder approval is obtained.

Because the Company’s common stock is listed on the NYSE, the Company is subject to the NYSE’s rules and regulations. NYSE Rule 312.03(c) requires stockholder approval prior to the issuance of common stock, or securities convertible into or exercisable for common stock, in any transaction or series of transactions if (i) the common stock to be issued has, or will have upon issuance, voting power equal to or in excess of 20% of the voting power outstanding before the issuance of such stock or of securities convertible into or exercisable for common stock, or (ii) the number of shares of common stock to be issued is, or will be upon issuance, equal to or in excess of 20% of the number of shares of common stock outstanding before the issuance of the common stock or of securities convertible into or exercisable for common stock. If the Company obtains stockholder approval, the Convertible Notes will be convertible, subject to various conditions and during certain periods, into cash, shares of the Company’s common stock or a combination of cash and shares of the Company’s common stock, at the Company’s election. If the Issuance Proposal is not approved prior to the relevant conversion date, the Company will be required to pay to holders in respect of each $1,000 principal amount of Convertible Notes being converted solely an amount in cash as if the Company had elected a “cash settlement.”

At the Special Meeting, in accordance with NYSE Rule 312.03(c), you will be asked to consider and vote on a proposal to approve the Issuance Proposal.

Unless and until the Issuance Proposal is approved by the Company’s stockholders, the conversion option that is part of the Convertible Notes will be accounted for as a derivative liability pursuant to accounting standards relating to derivative instruments and hedging activities (notwithstanding other factors to be evaluated by the Company each reporting period regarding the classification of derivative instruments).

For each financial statement period after issuance of the Convertible Notes, a hedge gain (or loss) will be reported in the Company’s income statement to the extent the valuation of the derivative liability

changes from the previous period as a result of changes in the market price of the Company’s common stock or changes in other valuation inputs and assumptions. For example, if the stock price increases, the value of the option increases and there would be a hedge loss reported in the period. This could result in significant fluctuations in the Company’s consolidated statement of comprehensive income (loss) from period to period and have a material adverse effect on the Company’s earnings per share. In addition, if the Company is required to settle its obligations in respect of the Convertible Notes solely in cash, the Company’s cash flow and liquidity position could be adversely impacted.

Whether the Issuance Proposal is approved at the Special Meeting will have no effect on the acquisition of NBIC Holdings, Inc.

Required Vote

The Issuance Proposal requires the affirmative vote of a majority of the shares of our common stock voting thereon at a meeting at which a quorum is present. Under applicable NYSE Rules, abstentions are counted as shares voted with respect to such proposal, and therefore, if you return your proxy card and “ABSTAIN” from voting, it will have the same effect as a vote against the Issuance Proposal.

Recommendation

The Board of Directors unanimously recommends that you vote “FOR” the Issuance Proposal.

Description of the Convertible Notes

The following is a summary of the principal terms of the Convertible Notes.

The Company issued the Convertible Notes under an Indenture (the “Indenture”), dated as of August 16, 2017, by and among the Company, as issuer, Heritage MGA, LLC, as guarantor (the “Guarantor”) and Wilmington Trust, National Association, as trustee (the “Trustee”).

The Convertible Notes bear interest at a rate of 5.875% per year. Interest accrues from August 16, 2017 and will be payable semi-annually in arrears, on February 1 and August 1 of each year, beginning on February 1, 2018. The Convertible Notes are senior unsecured obligations of the Company that rank senior in right of payment to the Company’s future indebtedness that is expressly subordinated in right of payment to the Convertible Notes; equal in right of payment to the Company’s unsecured indebtedness that is not so subordinated; effectively junior to any of the Company’s secured indebtedness to the extent of the value of the assets securing such indebtedness; and structurally junior to all indebtedness or other liabilities incurred by the Company’s subsidiaries other than the Guarantor, which will fully and unconditionally guarantee the Convertible Notes on a senior unsecured basis.

The Convertible Notes will mature on August 1, 2037 (the “Maturity Date”), unless earlier repurchased, redeemed or converted.

Holders may convert their Convertible Notes at any time prior to the close of business on the business day immediately preceding February 1, 2037, other than during the period from, and including, February 1, 2022 to the close of business on the second business day immediately preceding August 5, 2022, only under the following circumstances: (1) during any calendar quarter commencing after the calendar quarter ending on September 30, 2017, if the closing sale price of the Company’s common stock, for at least 20 trading days (whether or not consecutive) in the period of 30 consecutive trading days ending on the last trading day of the calendar quarter immediately preceding the calendar quarter

in which the conversion occurs, is more than 130% of the conversion price of the Convertible Notes in effect on each applicable trading day; (2) during the ten consecutive business-day period following any five consecutive trading-day period in which the trading price for the Convertible Notes for each such trading day was less than 98% of the closing sale price of the Company’s common stock on such date multiplied by the then-current conversion rate; (3) if the Company calls any or all of the Convertible Notes for redemption, at any time prior to the close of business on the second business day immediately preceding the redemption date; or (4) upon the occurrence of specified corporate events.

During the period from, and including, February 1, 2022 to the close of business on the second business day immediately preceding August 5, 2022, and on or after February 1, 2037 until the close of business on the second business day immediately preceding the Maturity Date, holders may surrender their Convertible Notes for conversion at any time, regardless of the foregoing circumstances.

Unless and until the Company obtains stockholder approval under NYSE Rule 312.03(c) for the issuance of the Company’s common stock in excess of the limitations set forth therein, the Company will pay to any converting holder in respect of each $1,000 principal amount of Convertible Notes being converted solely cash in an amount equal to the sum of the daily conversion values (as defined in the Indenture) for each of the 40 consecutive trading days during the related conversion period (as defined in the Indenture). Following the Company’s receipt of stockholder approval, the Company will settle conversions of Convertible Notes through payment or delivery, as the case may be, of cash, shares of its common stock or a combination of cash and shares of its common stock, at its election, based on such daily conversion values (other than for settlement only in shares).

The conversion rate for the Convertible Notes is initially 67.0264 shares of common stock per $1,000 principal amount of Convertible Notes (equivalent to an initial conversion price of approximately $14.92 per share of common stock). The conversion rate is subject to adjustment in certain circumstances, and is subject to increase for holders that elect to convert their Convertible Notes in connection with certain corporate transactions (but not, at the Company’s election, a public acquirer change of control (as defined in the Indenture)) that occur prior to August 5, 2022.

Upon the occurrence of a fundamental change (as defined in the Indenture) (but not, at the Company’s election, a public acquirer change of control (as defined in the Indenture)), holders of the Convertible Notes may require the Company to repurchase for cash all or a portion of their Notes at a fundamental change repurchase price equal to 100% of the principal amount of the Convertible Notes to be repurchased, plus accrued and unpaid interest to, but excluding, the fundamental change repurchase date.

Except as described below, the Company may not redeem the Convertible Notes prior to August 5, 2022. If the Company’s previously announced pending NBIC Acquisition is not consummated for any reason by June 8, 2018, or if the acquisition agreement relating to the NBIC Acquisition is terminated for any reason (other than by consummation of the NBIC Acquisition), the Company may redeem all, but not less than all, of the outstanding Convertible Notes for cash on a redemption date to occur on or prior to August 31, 2018 for a redemption price for each $1,000 principal amount of Convertible Notes equal to the sum of (i) $1,010, (ii) accrued and unpaid interest on such Convertible Notes to, but excluding, the redemption date and (iii) 75% of the excess, if any, of the redemption conversion value (as defined in the Indenture) over the initial conversion value (as defined in the Indenture). On or after August 5, 2022 but prior to February 1, 2037, the Company may redeem for cash all or any portion of the Convertible Notes, at the Company’s option, at a redemption price equal to 100% of the principal

amount of the Convertible Notes to be redeemed, plus accrued and unpaid interest to, but excluding, the redemption date. No sinking fund is provided for the Convertible Notes, which means that the Company is not required to redeem or retire the Convertible Notes periodically. Holders of the Convertible Notes will be able to cause the Company to repurchase their Convertible Notes for cash on any of August 1, 2022, August 1, 2027 and August 1, 2032, in each case at 100% of their principal amount, plus accrued and unpaid interest to, but excluding, the relevant repurchase date.

The Indenture contains customary terms and covenants and events of default. If an Event of Default (as defined in the Indenture) occurs and is continuing, the Trustee by notice to the Company, or the holders of at least 25% in aggregate principal amount of the Convertible Notes then outstanding by notice to the Company and the Trustee, may declare 100% of the principal of, and accrued and unpaid interest, if any, on, all the Convertible Notes to be immediately due and payable. In the case of certain events of bankruptcy, insolvency or reorganization (as set forth in the Indenture) with respect to the Company, 100% of the principal of, and accrued and unpaid interest, if any, on, the Convertible Notes will automatically become immediately due and payable.

The foregoing description of the terms of the Convertible Notes is not complete and is qualified in its entirety by reference to the text of the Indenture, dated as of August 16, 2017, and the Form of 5.875% Convertible Senior Note due 2037, filed as Exhibit 4.1 and 4.2, respectively, to the Company’s Form 8-K filed on August 16, 2017.Florida.

ADJOURNMENT PROPOSAL—APPROVAL OF THE ADJOURNMENT OR
POSTPONEMENT OF THE SPECIAL MEETINGSTOCK OWNERSHIP

The Company’s stockholders are being asked to consider and vote on a proposal to adjourn or postpone the Special Meeting, if necessary, to solicit additional proxies. The Board of Directors believes this proposal to be in the best interests of the Company’s stockholders because it gives the Company flexibility to solicit the vote of additional holders of the Company’s voting securities to vote on matters the Board of Directors deems important to the Company. If the Issuance Proposal is not approved in accordance with Section 312.03(c) of The New York Stock Exchange Listed Company Manual prior to the relevant conversion date, the Company will pay to holders in respect of each $1,000 principal amount of Convertible Notes being converted solely an amount in cash as if the Company had elected a “cash settlement”. See “Issuance Proposal—Approval of the Issuance of Company Common Stock Upon Conversion of the Convertible Notes” for details regarding the consequences of a failure to receive the required vote to approve the Issuance Proposal.The Board of Directors of the Company recommends that stockholders vote “FOR” the Proposal to adjourn or postpone the Special Meeting, if necessary, to solicit additional proxies.

SECURITY OWNERSHIP OF CERTAIN BENEFICIAL OWNERS AND MANAGEMENTSecurity Ownership of Certain Beneficial Owners and Management

The following table sets forth certain information regarding the beneficial ownership of our common stock as of October 16, 2017, the Record DateApril 23, 2018 (except as indicated below) by:

 

·all persons known by us to own beneficially 5% or more of our outstanding common stock;
all persons known by us to own beneficially 5% or more of our outstanding common stock;

 

·each of our directors and director nominees;
each of our directors and director nominees;

 

·each of our named executive officers; and
each of our named executive officers listed in the “EXECUTIVE AND DIRECTOR COMPENSATION” section of this proxy statement; and

 

·all of our directors and executive officers as a group.
all of our directors and executive officers as a group.

Unless otherwise indicated, the address of each beneficial owner listed below is c/o Heritage Insurance Holdings, Inc., 2600 McCormick Drive, Suite 300, Clearwater, Florida 33759.

 

 Number of
Shares
Beneficially
Owned(1)
   Approximate
Percent of
Class(1)
 

Name and Address

     Number of
Shares
Beneficially
Owned(1)
 Approximate
Percent of
Class(1)
 

CERTAIN BENEFICIAL OWNERS

(not including directors and executive officers):

         

The Vanguard Group(2)
100 Vanguard Blvd.
Malvern, PA 19355

  1,962,911     8.0

BlackRock, Inc.(3)
55 East 52nd Street
New York, NY 10055

  2,063,401     8.5

Creative Planning(4)
3400 College Boulevard
Leawood, KS 66211

  1,531,542     6.3

BlackRock, Inc.(2)

55 East 52nd Street

New York, NY 10055

   1,770,864  6.7

DIRECTORS AND NAMED EXECUTIVE OFFICERS:

         

Bruce Lucas

  1,797,703   (5)   7.2   1,262,510(3)  4.8

Richard Widdicombe

  1,025,612   (6)   4.2   761,778  2.9

Ernie Garateix

  250,669   (7)   1.0   140,754  

Kirk Lusk

   122,831(4)  

Pete Apostolou

  170,000   (8)   *    160,000  

Irini Barlas

  45,100   (9)   *    45,162(5)  

Trifon Houvardas

  358,855   (10)   1.5   348,855(6)  1.3

Steven Martindale

   —     —   

James Masiello

  379,131   (11)   1.6   353,490(7)  1.3

Nicholas Pappas

  76,595   (12)   *    63,745(8)  

Joseph Vattamattam

  61,441   (8)   *    51,441  

Vijay Walvekar

  377,181   (13)   1.5   335,889(9)  1.3

Steven Martindale

        

All directors and executive officers as a group (11 persons)

  4,542,287   (14)   17.9

All directors and executive officers as a group (15 persons)

   6,724,966  25.3

 

*= less than 1%

(1)“Beneficial ownership” means any person who, directly or indirectly, has or shares voting or investment power with respect to a security or has the right to acquire such power within 60 days. Shares of common stock subject to options that are currently exercisable or exercisable within 60 days of October 16, 2017, the Record Date,April 23, 2018 are deemed outstanding for computing the ownership percentage of the person holding such options, but are not deemed outstanding for computing the ownership percentage of any other person. The number of shares beneficially owned is determined as of October 16, 2017, the Record Date,April 23, 2018, and the percentages are based upon 24,400,17426,569,804 shares of our common stock outstanding as of October 16, 2017, the Record Date.April 23, 2018. Unless otherwise indicated, each stockholder listed below has sole voting and investment power with respect to the shares of common stock beneficially owned by such stockholder.
(2)Based solely on a Schedule 13G filed with the SEC on February 13, 2017.January 24, 2018.
(3)Based solely on a Schedule 13G filed with the SEC on January 30, 2017.
(4)Based solely on a Schedule 13F filed with the SEC on April 7, 2017.
(5)Includes 494,612 shares held by the Alec Lucas Trust and 122,020(i) 67,600 shares held by IIM Holdings, LLC and IIM Holdings II, LLC, entities controlled by Mr. Lucas. Also includes exercisable options to purchase 500,000Lucas and (ii) 213,037 shares of common stock.held by the Alec Lucas Trust.
(6)(4)Includes exercisable options to purchase 250,000Represents (i) 75,000 shares of common stock.restricted stock awarded to Mr. Lusk pursuant to the Omnibus Incentive Plan and (ii) 47,831 shares issued in connection with the previously disclosed acquisition of NBIC Holdings, Inc., which was completed on November 30, 2017.
(7)Includes exercisable options to purchase 100,000 shares of common stock.
(8)Includes exercisable options to purchase 10,000 shares of common stock.
(9)(5)Includes 30,900 shares held by the Lee M. Barlas and Irini Barlas Living Trust.Trust and 5,022 shares held by Ms. Barlas’ spouse.
(10)(6)Includes 308,605 shares held by K&M Insurance Investors, LLC, an entity controlled by Mr. Houvardas. Also includes exercisable options to purchase 10,000 shares of common stock.
(11)(7)Includes 22,195 shares held by Mr. Masiello’s wife and 91,500 shares held by Alliance Holdings, Inc., an entity controlled by Mr. Masiello and members of his family. Also includes exercisable options to purchase 25,641 shares of common stock.
(12)(8)These shares are held jointly by Mr. Pappas and his father. Includes exercisable options to purchase 10,000 shares of common stock.
(13)(9)Includes 287,889 shares held by Mr. Walvekar’s wife. Also, includes exercisable options to purchase 41,282 shares of common stock.
(14)Includes exercisable options to purchase 968,135 shares of common stock.

OTHER MATTERSSection 16(a) Beneficial Ownership Reporting Compliance

NoSection 16(a) of the Exchange Act requires our directors, executive officers and holders of more than 10% of our common stock to file with the SEC reports regarding their ownership and changes in ownership of our common stock. They are also required to provide us with copies of any forms they file.

Based solely on our review of the reports furnished to us, we believe that during the last fiscal year, all reports filed by our directors and executive officers under Section 16(a) were made timely, except that a Form 4 for James Masiello was untimely filed on February 27, 2017; a Form 4 for Vijay Walvekar was untimely filed on March 28, 2017; and a Form 4 for Joseph Vattamattam was untimely filed on August 23, 2017.

CERTAIN RELATIONSHIPS AND RELATED PARTY TRANSACTIONS

In the ordinary course of our business, we have entered into transactions with our directors, officers and 5% or greater stockholders or companies in which they have a material interest. Our Audit Committee is responsible for approving related party transactions, as defined in applicable rules promulgated by the SEC. Our Audit Committee operates under a written charter pursuant to which all related party transactions are reviewed for potential conflicts of interest. Such transactions must be approved by our Audit Committee.

Agreement with Shannon Lucas

On January 1, 2017, Shannon Lucas, the wife of our Chairman and CEO, entered into a consulting agreement with the Company, pursuant to which she agreed to provide consulting services related to the Company’s catastrophe reinsurance and risk management program to us at a rate of $400 per hour. In 2017, Ms. Lucas received total cash compensation of approximately $440,000. The consulting agreement has no specific term and either party may terminate the agreement upon providing written notice. Additionally, Ms. Lucas currently serves as a director of our subsidiary Heritage Property & Casualty Insurance Company (“HPCI”). Ms. Lucas’ annual compensation for her role as a director of HPCI is $150,000.

Employment of Bob DeBoy

Bob DeBoy, thebrother-in-law of Bruce Lucas, joined the Company in February 2013 as a Claims Examiner. Mr. DeBoy reports directly to a Claims Manager. In 2017, Mr. DeBoy received total cash compensation of approximately $185,239. Mr DeBoy also participates in the Company’s benefit plans that are made available to all employees.

Employment of Kevin Widdicombe

Kevin Widdicombe, the son of Richard Widdicombe, joined the Company in July 2013 as a Risk Modeling Analyst. Mr. Widdicombe reports directly to the Data Warehouse Manager. In 2017, Mr. Widdicombe received total cash compensation of approximately $205,035. Mr. Widdicombe also participates in the Company’s benefit plans that are made available to all employees.

EXECUTIVE COMPENSATION

Executive Compensation Program Summary

Our executive compensation program in 2017 for Messrs. Lucas, Widdicombe and Garateix consisted of three primary elements:

BaseSalary – We intend to provide base salaries, which are generally competitive with salaries of similarly-situated executives at comparable companies.

AnnualIncentiveAward – We provided annual incentive awards, which were based on our EBITDA performance and commensurate with our EBITDA performance in 2017.

Long-Term Equity Awards –We did not grant any restricted stock to our named executive officers in 2017 because the grants we made in 2015 were intended to compensate our named executive officers over the next five years. However, our Compensation Committee reserves the right to alter its grant practice in light of business needs and changes in applicable laws and regulations, including the Tax Cuts and Jobs Acts and related repeal of the performance-based compensation exception under Section 162(m) of the Internal Revenue Code of 1986, as amended.

Each of these elements is described in more detail in the following tables and narrative descriptions.

Summary Compensation Table

The following Summary Compensation Table discloses the compensation information for fiscal years 2016 and 2017 for our principal executive officer (“PEO”) and the two most highly compensated executive officers other than that set forththe PEO who were serving as executive officers at the end of the last completed fiscal year (our “named executive officers”). Certain information regarding 2017 compensation and other information is provided in the attached noticenarrative sections following the Summary Compensation Table.

Name and Principal

Position

  Year   Salary
($)
   Bonus
($)(1)
   Stock Awards
($)
   Option
Awards
($)
   Non-Equity
Incentive Plan
Compensation(2)
   All Other
Compensation
($)(3)
   Total
($)
 

Bruce Lucas

   2017    2,059,885    —      —      —      4,633,022    44,911    6,737,818 

Chairman and CEO

   2016    2,000,000    —      —      —      4,776,500    40,023    6,816,523 

Richard Widdicombe

   2017    1,802,164    137,000   —      —      750,000    51,035    2,740,698 

President

   2016    1,750,000    —      —      —      750,000    55,858    2,555,858 

Ernie Garateix

   2017    772,626    55,000   —      —      400,000    36,334    1,263,960 

Chief Operating Officer

   2016    750,000    —      —      —      150,000    157,708    1,057,708 

(1)Discretionary bonus award to and paid to the Messrs. Widdicombe and Garateix in 2017.
(2)For details of thenon-equity incentive plan compensation provided to our named executive officers during 2017, please see the “Employment Agreements” section below.
(3)Each of Messrs. Lucas and Garateix received an automobile allowance during 2017. The amounts disclosed above include Company contributions with respect to the Company 401(k) plan and pension plan and the excess portion of the employer share of premiums offered to our named executive officers with respect to the following benefits: health insurance, dental insurance, vision insurance, life insurance, short-term disability insurance, long-term disability insurance, an additional disability insurance policy and an additional life insurance policy for Messrs. Lucas, Widdicombe and Garateix.

Base Salaries

Our named executive officers were entitled to the following annual base salaries:

Named Executive Officer

  2017 Base Salary
(Effective January 1, 2017)
   2018 Base Salary
(Effective January 1, 2018)
 

Bruce Lucas

  $2,100,000   $2,205,000 

Richard Widdicombe

  $1,837,500   $1,929,375 

Ernie Garateix

  $787,500   $900,000 

Annual Incentive Awards

As described below, our named executive officers are entitled to certain annual incentive awards, pursuant to their employment agreements or as otherwise approved by our Compensation Committee.

Severance and Change of Special Meeting is expectedControl Agreements

Our named executive officers are not parties to come beforeany separate severance or change of control agreements. As described below, our named executive officers are entitled to certain severance and change of control payments and benefits pursuant to their employment agreements.

Employee Benefits

Our named executive officers participate in other employee benefit plans generally available to all employees on the Special Meeting. However, shouldsame terms, such as medical, dental, life, disability insurance programs and a 401(k) plan, except as noted in the Summary Compensation Table. In 2017, we provided nonelective contributions to the 401(k) accounts of all our employees, including our named executive officers, equal to 3% of his or her annual compensation, subject to applicable limitations. We do not provide our named executive officers with any other matters requiringmaterial perquisites or similar personal benefits.

Employment Agreements

Mr. Lucas’ Employment Agreement

Effective November 4, 2015, Mr. Lucas entered into an amended and restated employment agreement (the “Lucas Amended Agreement”) with us to serve as our Chief Executive Officer until December 31, 2020. The Lucas Amended Agreement provides for (i) an annual base salary of $2.0 million commencing on January 1, 2016 (subject to annual cost of living and inflation-based adjustments), (ii) an incentive bonus under our Omnibus Incentive Plan of $1.75 million for each calendar year, beginning in 2016, subject to the Company’s achievement of at least $50 million in EBITDA for such year and (iii) an annual cash bonus under the Company’s EBITDA bonus pool with a votetarget amount equal to the greater of stockholders arise,(A) $2.5 million or (B) the persons namedremainder of the Company’s bonus pool after paying all employee bonuses. In connection with entering into the Lucas Amended Agreement, Mr. Lucas received a grant of 750,000 shares of restricted stock, which vest in equal annual installments of 150,000 shares beginning on November 4, 2016.

Mr. Lucas would be entitled to his base salary and share-based compensation payments for the remainder of the employment term, under the Lucas Amended Agreement, in the accompanying proxy will vote thereon accordingevent he is terminated by us without “Cause,” which is defined as (i) a breach of the employment agreement or (ii) any fraud, breach of fiduciary duty, gross negligence, embezzlement or misappropriation against the Company. If the Lucas Amended Agreement, expires without the Company offering him a new employment agreement with compensation levels similar to their best judgmentthose offered under this agreement in the interestlast year of its term, then he would be entitled to severance equal to his annual base salary in the final year of the Company.agreement.

PROXY SOLICITATION AND COSTSIf Mr. Lucas dies during the term of the Lucas Amended Agreement, his estate would be entitled to 50% of his base salary for the remainder of the employment term.

It is expected thatMr. Lucas may resign upon giving no less than 90 days’ notice.

If Mr. Lucas shall become unable to perform his duties by reason of illness or injury for a consecutive period of ninety (90) days, then the solicitationCompany may, within thirty (30) days, suspend of proxies will be primarily by mail. Proxies may also be solicited personally by regular employeesthe officership of Mr. Lucas. In the event of such suspension, Mr. Lucas shall remain an employee of the Company by telephone or by other meansand receive its regular compensation and all its regular fringe benefits as set forth above through December 31st of communicationthe following year, in which case Mr. Lucas’ employment with the Company shall terminate at nominal cost.the end of such period if Mr. Lucas has not returned to the full-time performance of his duties.

In the event of a “change of control” (as defined in the Lucas Amended Agreement), Mr. Lucas would be entitled to continue receiving, through the remainder of the term of the Lucas Amended Agreement, (i) his base salary as in effect on the change of control date, (ii) his annual bonuses in amounts no less than those paid in the preceding 12 months and (iii) employee benefits as in effect on the change of control date.

Upon a termination of employment for any reason, Mr. Lucas would continue to be subject tonon-solicitation andnon-competition restrictive covenants for periods of one year and two years, respectively, following such termination.

Mr. Widdicombe’s Employment Agreement

Effective November 4, 2015, Mr. Widdicombe entered into an amended and restated employment agreement (the “Widdicombe Amended Agreement”) with us to serve as President of the Company until December 31, 2020. The Company will bear theWiddicombe Amended Agreement provides for (i) an annual base salary of $1.75 million commencing on January 1, 2016 (subject to annual cost of living and inflation-based adjustments), (ii) an incentive bonus under the Omnibus Incentive Plan of $375,000 for each calendar year beginning in 2016, subject to the Company’s achievement of at least $50 million in EBITDA for such solicitation. It will reimburse banks, brokersyear and trustees,(iii) an annual cash bonus under the Company’s EBITDA bonus pool with a target amount of $375,000 beginning in 2016. In connection with entering into the Widdicombe Amended Agreement, Mr. Widdicombe received a grant of 250,000 shares of restricted stock, which vest in equal annual installments of 50,000 shares beginning on November 4, 2016.

Mr. Widdicombe would be entitled to his base salary and share based compensation for the remainder of the employment term, under the Widdicombe Amended Agreement, in the event he is terminated by us without “Cause,” which is defined as (i) a breach of the employment agreement or their nominees,(ii) any fraud, breach of fiduciary duty, gross negligence, embezzlement or misappropriation against the Company. If the Widdicombe Amended Agreement expires without the Company offering him a new employment agreement with compensation levels similar to those offered under this agreement in the last year of its term, then he would be entitled to severance equal his annual base salary in the final year of the agreement.

If Mr. Widdicombe dies during the term of the Widdicombe Amended Agreement, his estate would be entitled to 50% of his base salary for reasonable expenses incurredthe remainder of the employment term.

Mr. Widdicombe may resign upon giving no less than 90 days’ notice.

If Mr. Widdicombe shall become unable to perform his duties as provided for herein by themreason of illness or injury for a consecutive period of ninety (90) days, then the Company may, within thirty (30) days, suspend of the officership of Mr. Widdicombe. In the event of such suspension, Mr. Widdicombe shall remain an employee of the Company and receive its regular compensation and all its regular fringe benefits as set forth above through December 31st of the following year, in forwarding proxy materialwhich case Mr. Widdicombe’s employment with the Company shall terminate at the end of such period if Mr. Widdicombe has not returned to beneficial ownersthe full-time performance of his duties.

In the event of a “change of control” (as defined in the agreement), Mr. Widdicombe would be entitled to continue receiving, through the remainder of the term of the agreement, (i) his base salary as in effect on the change of control date, (ii) his annual bonuses in amounts no less than those paid in the preceding 12 months and (iii) employee benefits as in effect on the change of control date.

Upon a termination of employment for any reason, Mr. Widdicombe would continue to be subject tonon-solicitation andnon-competition restrictive covenants for periods of one year and two years, respectively, following such termination.

Mr. Garateix’s Employment Agreement

Effective November 4, 2015, Mr. Garateix entered into an employment agreement (the “Garateix Amended Agreement”) with us to serve as our Chief Operating Officer of the Company until December 31, 2020. The Garateix Amended Agreement provides for (i) an annual base salary of $750,000 commencing on January 1, 2016 (subject to annual cost of living and inflation-based adjustments) and (ii) an annual cash bonus of up to $100,000 under the Company’s EBITDA bonus pool during the term of the Garateix Amended Agreement, based on and subject to available funds in the Company’s EBITDA bonus pool. In connection with the Garateix Amended Agreement, Mr. Garateix received a grant of 125,000 shares of restricted stock, which vest in equal annual installments of 25,000 shares beginning on November 4, 2016.

Mr. Garateix may resign upon giving no less than 90 days’ notice.

Upon a termination of employment for any reason, Mr. Garateix would be subject tonon-solicitation andnon-competition restrictive covenants for periods of five years and two years, respectively, following such termination.

Outstanding Equity Awards at 2017 FiscalYear-End

   Option Awards   Stock Awards 
Name  Number of
Securities
Underlying
Unexercised
Options (#)
Exercisable
   Number of
Securities
Underlying
Unexercised
Options (#)
Unexercisable
   Option
Exercise Price
($)
   Option
Expiration
Date
($)
   Number of
Shares of or
Units of Stock
that Have Not
Vested (#)(1)
   Market Value of
Shares of
Units of Stock
that Have Not
Vested ($)(1)
 

Bruce Lucas

   —      —      —      —      450,000    8,109,000 
   —      —      —      —       

Richard Widdicombe

   —      —      —      —      150,000    2,703,000 
   —      —      —      —       

Ernie Garateix

   —      —      —      —      75,000    1,351,500 

(1)These restricted stock awards were granted on November 4, 2015, which have ratable annual vesting over five years’, subject to the executive’s continued employment with the Company through such date. The market value of these shares is shown based on the closing price of the Company’s stock on December 29, 2017, which was $18.02 per share.

Narrative to Outstanding Equity Awards Table

All awards reported in the table above were granted under the Omnibus Incentive Plan, which was disclosed and adopted in connection with our initial public offering.

DIRECTOR COMPENSATION

As described more fully below, the following table summarizes the annual compensation for ournon-employee directors during 2017.

2017 Director Compensation

Name  Fees Earned or
Paid in Cash
($)(1)
   Option Awards
($)(2)
   Total
($)
 

Pete Apostolou

   150,000    —      150,000 

Irini Barlas

   150,000    —      150,000 

Trifon Houvardas

   150,000    —      150,000 

James Masiello

   158,603    —      158,603 

Nicholas Pappas

   150,000    —      150,000 

Joseph Vattamattam

   150,000    —      150,000 

Vijay Walvekar

   167,205    —      167,205 

(1)All of ournon-employee directors received annual cash payments in connection with their provision of services to the Board during 2017, which totaled $150,000. In addition, Messrs. Masiello and Walvekar received additional cash compensation of $8,603 and $17,205, respectively.
(2)We did not grant any stock options to ournon-employee directors in 2017. As of December 31, 2017, none of ournon-employee directors held any unexercised stock options.

Narrative to Director Compensation Table

The table above describes the compensation earned by ournon-employee directors in 2017. Our processes and procedures for considering and determining the amount of compensation we pay ournon-employee directors consist of a periodic review of director compensation by the Board.

AUDIT COMMITTEE REPORT

The Audit Committee of the Board consists of threenon-employee directors, Irini Barlas, Trifon Houvardas and Vijay Walvekar, each of whom the Board has determined to be an independent director as defined in the rules of the NYSE. The Audit Committee is a standing committee of the Board and operates under a written charter adopted by the Board, which is available at www.heritagepci.com on the “Investor” page under the link “Corporate Governance.” Among its other functions, the Audit Committee has the authority and responsibility to retain and terminate the engagement of the Company’s independent registered public accounting firm (the “independent auditors”).

Management is responsible for the Company’s internal controls and the financial reporting process. The independent auditors are responsible for performing an independent audit of the Company’s consolidated financial statements in accordance with the NYSE scheduleauditing standards of charges.the Public Company Accounting Oversight Board (United States) and to issue a report thereon. The Audit Committee’s responsibility is to monitor and oversee these processes.

During 2017, at each of its meetings, the Audit Committee met with the senior members of the Company’s financial management team and the independent auditors. The Audit Committee’s agenda is established by the Audit Committee’s chairwoman and senior members of the Company’s financial management team. The Audit Committee met in private sessions with the Company’s independent auditors at certain of its meetings, and also separately with the Company’s head of internal audit, without management representation, to discuss financial management, accounting and internal control issues. The Audit Committee has reviewed and discussed with management and the independent auditors the audited consolidated financial statements in the Company’s Annual Report onForm 10-K for the year ended December 31, 2017, 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 consolidated financial statements. Management represented to the Audit Committee that the Company’s consolidated financial statements were prepared in accordance with generally accepted accounting principles. The Audit Committee discussed with the independent auditors matters required to be discussed by the Statement on Auditing Standards No. 61, “Communication with Audit Committees,” as amended, as adopted by the Public Company Accounting Oversight Board in Rule 3200T.

The Company will bear the entire cost of this solicitation of proxies, including the preparation, assembly, printing and mailing of this proxy statement, the proxy card and any additional solicitation material that the Company may provide to stockholders. Copies of solicitation material will beCompany’s independent auditors also provided to brokerage firms, fiduciariesthe Audit Committee the written disclosures and custodians holding shares in their names that are beneficially ownedthe letter required by others so that they may forward the solicitation material to such beneficial owners. Further, the original solicitation of proxies by mail may be supplemented by solicitation by telephone and other means by directors, executive officers and employees of the Company. No additional compensation will be paid to these individuals for any such services. The Company will also post its proxy materials to its website under “Investors.” In addition, the Company has retained Georgeson LLC to act as a proxy solicitor in conjunction with the Special Meeting. The Company has agreed to pay that firm approximately $15,000.00 plus reasonable out-of-pocket expenses, for proxy solicitation services.

WHERE YOU CAN FIND MORE INFORMATION

The Company is subject to the informationalapplicable requirements of the Securities Exchange Act of 1934, as amended, and, in accordance therewith, files reports and other informationPublic Company Accounting Oversight Board regarding the independent accountant’s communications with the SEC. Any interested party may inspect information filedAudit Committee concerning independence. The Committee discussed with the independent auditors that firm’s independence and considered whether thenon-audit services provided by the Company, without charge, atindependent auditors are compatible with maintaining their independence.

Based on the public reference facilitiesAudit Committee’s discussion with management and the independent auditors, and the Audit Committee’s review of the SEC at its principal office at 100 F. Street, N.E., Washington, D.C. 20549. Any interested party may obtain copiesrepresentation of all or any portionmanagement and the report of the information filed byindependent auditors to the Company at prescribed rates fromAudit Committee, the Public Reference SectionAudit Committee recommended that the Board of Directors include the SEC at its principal office at 100 F. Street, N.E., Washington, D.C. 20549. In addition,audited consolidated financial statements in the SEC maintains an Internet site that contains reports, proxy and information statements and other information regardingCompany’s Annual Report onForm 10-K for the Company and other registrants that file electronically with the SEC at http://www.sec.gov.year ended December 31, 2017.

The Company’s common stock is listed on the NYSE and trades under the symbol “HRTG”.

Submitted by the Audit Committee of the Board of Directors,
Irini Barlas (Chairwoman)
Trifon Houvardas
Vijay Walvekar

INFORMATION INCORPORATEDFEES BILLED FOR SERVICES RENDERED BY REFERENCEINDEPENDENT REGISTERED

The SEC allows us to “incorporate by reference” into this proxy statementPUBLIC ACCOUNTING FIRM

For the information we file with them, which means that we can disclose important information to you by referring you to those documents. Any statement contained or incorporated by reference in this proxy statement shall be deemed to be modified or superseded for purposes of this proxy statement tofiscal years ended December 31, 2016 and 2017, Grant Thornton LLP, our independent registered public accounting firm, billed the extent that a statement

approximate fees set forth below:

contained herein, or in any subsequently filed document which also is incorporated by reference herein, modifies or supersedes such earlier statement. Any such statement so modified or superseded shall not be deemed, except as so modified or superseded, to constitute a part of this proxy statement. We incorporate by reference the documents listed below:

Fees

  Fiscal Year Ended
December 31,
2017
   Fiscal Year Ended
December 31,
2016
 

Audit Fees(1)

  $1,338,086   $749,814 

Audit-Related Fees(2)

   57,797    69,226 

Tax Fees

   78,236    107,933 

All Other Fees

   —      —   
  

 

 

   

 

 

 

Total

  $1,474,119   $926,973 

 

(1)·our Annual Report on Form 10-KAudit fees include fees billed for professional services rendered for the fiscalaudit of our annual consolidated financial statements, the review of the interim consolidated financial statements included in our quarterly reports, and other related services that are normally provided in connection with statutory and regulatory filings. Audit fees for the year ended December 31, 2016;2017 include periodic filings with the SEC.
(2)Audit-related fees consist of fees billed for assurance and related services that are reasonably related to the performance of the audit or review of the Company’s consolidated financial statements and are not reported under “Audit Fees.” These services include accounting consultations and due diligence in connection with mergers and acquisitions, attest services related to financial reporting that are not required by statute or regulation and consultations concerning financial accounting and reporting standards

The Audit Committee has adopted certain policies and procedures regarding permitted audit andnon-audit services and the annualpre-approval of such services. Each year, the Audit Committee will ratify the types of audit andnon-audit services of which management may wish to avail itself, subject topre-approval of specific services. Each year, management and the independent registered public accounting firm will jointly submit apre-approval request, which will list each known and/or anticipated audit andnon-audit services for the upcoming calendar year and which will include associated budgeted fees. The Audit Committee will review the requests and approve a list of annualpre-approvednon-audit services. Any additional interim requests for additionalnon-audit services that were not contained in the annualpre-approval request will be approved during quarterly Audit Committee meetings.

·our Quarterly Reports on Form 10-Q for the fiscal quarters ended March 31, 2017 and June 30, 2017;

·our Definitive Proxy Statement on Schedule 14A filed with the SEC on April 28, 2017;

·our Current Reports on Form 8-K filed on March 2, 2017, June 28, 2017, August 9, 2017 (except with respect to Items 2.02 and 7.01), August 16, 2017, August 22, 2017 and September 13, 2017; and

·the description of our capital stock as set forth in our Registration Statement on Form 8-A filed with the SEC on May 20, 2014.

All documents that we file (but not those that we furnish)services provided by Grant Thornton LLP during the fiscal year ended December 31, 2017 were approved by the Audit Committee.

OTHER INFORMATION

Stockholder Proposals for the 2019 Annual Meeting

If any stockholder intends to present a proposal to be considered for inclusion in the Company’s proxy materials in connection with the 2019 annual meeting of stockholders, the proposal must be in proper form (per SEC pursuant to Section 13(a), 13(c), 14 or 15(d)Regulation 14A,Rule 14a-8) and received by the Secretary of the Exchange Act afterCompany on or before December 28, 2018. Stockholder proposals to be presented at the date2019 annual meeting of stockholders which are not to be included in the Company’s proxy materials must be received by the Company no earlier than February 22, 2019 and no later than March 23, 2019, in accordance with the procedures in the Company’s Bylaws.

Expenses of Solicitation

The Company pays the cost of preparing, assembling and mailing this proxy-soliciting material. The Company pays all costs of solicitation, including certain expenses of brokers and nominees who mail proxy materials to their customers or principals.

“Householding” of Proxy Materials

The SEC has adopted rules that permit companies and intermediaries (e.g., brokers) to satisfy the delivery requirements for proxy statements 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 provides convenience for stockholders and beforecost savings for companies.

We have delivered only one notice to multiple stockholders who share an address, unless we received contrary instructions from the dateimpacted stockholders prior to the mailing date. We agree to deliver promptly, upon written or oral request, a separate copy of the Special Meeting are incorporated by referencenotice and, if applicable, proxy materials, as requested, to any stockholder at the shared address to which a single copy of these documents was delivered. Stockholders should contact their broker or, if a stockholder is a direct holder of shares of our common stock, they should submit their request to our transfer agent in this proxy statement from the date of filingwriting addressed to: Computershare Investor Services, P.O. Box 30170, College Station, Texas 77842-3170. In addition, stockholders who currently receive multiple copies of the documents, unlessnotice at their address and would like to request “householding” of their communications should contact their broker or, if a stockholder is a direct holder of shares of our common stock, they should submit a request to our transfer agent in writing at the address above.

Upon request by any stockholder entitled to vote at the Annual Meeting, we specifically provide otherwise. Information that we file with the SEC will automatically update and may replace information previously filed with the SEC.

You may obtain,promptly furnish without charge a separate copy of any of the documents incorporated by reference in thisour proxy statement other than exhibitsor annual report to those documents that are not specifically incorporated by reference into those documents, by writingyou upon written or telephoning us at the following address:oral request to: Investor Relations, Heritage Insurance Holdings, Inc., 2600 McCormick Drive Suite 300, Clearwater, Florida 33759, phone number (727) 727-7200.

Information contained on our website,www.heritagepci.com, is not incorporatedor by reference in, and does not constitute part of, this proxy statement.

AVAILABILITY OF FORM 10-K AND ANNUAL REPORT TO STOCKHOLDERS

Copies of the Annual Report, which also contains the Company’s Annual Report on Form 10-K for the fiscal year ended December 31, 2016 (not including exhibits and documents incorporated by reference), are available without charge to stockholders upon written request to the Companytelephone at Heritage Insurance Holdings, Inc., 2600 McCormick Drive, Suite 300, Clearwater, Florida 33759, Attn: Investor Relations.727-362-7200.

HERITAGE INSURANCE HOLDINGS, INC.
ATTN: STEVEN MARTINDALE

2600 MCCORMICK DRIVE, SUITE 300
CLEARWATER, FL 33759

LOGO
LOGO
 

VOTE BY INTERNET -

www.investorvote.com/HRTGElectronic Voting Instructions

 

UseAvailable 24 hours a day, 7 days a week!

Instead of mailing your proxy, you may choose one of the voting methods outlined below to vote your proxy.

VALIDATION DETAILS ARE LOCATED BELOW IN THE TITLE BAR.

Proxies submitted by the Internet or telephone must be received by 11:59 p.m., EST, on June 21, 2018.

LOGOVote by Internet

•  Go to transmitwww.investorvote.com/HRTG

•  Or scan the QR code with your voting instructions and for electronic delivery of information up until 11:59 P.M. Eastern Timesmartphone

•  Follow the day beforesteps outlined on the secure website

Vote by telephone

cut-offUsing ablack ink pen, mark your votes with anX as shown in this example. Please do not write outside the designated areas.

•  Call toll free1-800-652-VOTE date or meeting date. Have your proxy card in hand when you access(8683) within the web site and followUSA, US territories & Canada on a touch tone telephone

•  Follow the instructions to obtain your records and to create an electronic voting instruction form.provided by the recorded message

LOGO

 

q IF YOU HAVE NOT VOTED VIA THE INTERNETOR TELEPHONE, FOLD ALONG THE PERFORATION, DETACH AND RETURN THE

VOTE BY PHONE -BOTTOM PORTION IN THE ENCLOSED ENVELOPE.1-800-652-VOTEq (8683)

 

Use any touch-tone telephone to transmit your voting instructions up until 11:59 P.M. Eastern Time the day before thecut-off date or meeting date. 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.

TO VOTE, MARK BLOCKS BELOW IN BLUE OR BLACK INK AS

FOLLOWS:

KEEP THIS PORTION FOR YOUR

RECORDS

 

 A Proposals — The Board of Directors recommends a voteFOR all the nominees listed andFOR Proposal 2.

+

1.Election of Directors:ForWithholdForWithholdForWithhold

 THIS PROXY CARD IS VALID ONLY WHEN SIGNED AND DATED.

01 - Bruce Lucas

 

DETACH AND RETURN THIS

PORTION ONLY

02 - Richard Widdicombe

03 - Panagiotis (Pete) Apostolou

  

The Board of Directors recommends you vote FOR proposals 1 and 2.

ForAgainstAbstain

1      To approve, pursuant to NYSE Rule 312.03(c), the issuance of our common stock upon conversion of our 5.875% Senior Convertible Notes due 2037.

04 - Irini Barlas
     

2      To adjourn or postpone the special meeting, if necessary, to solicit additional proxies.

05 - Trifon Houvardas
     06 - Steven Martindale  
NOTE: Such other business as may properly come before the meeting or any adjournment 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 authorized officer.

07 - James Masiello
08 - Nicholas Pappas09 - Joseph Vattamattam
10 - Vijay Walvekar         

 

 ForAgainstAbstain
2.Ratification of the appointment of Grant Thornton LLP as the independent registered public accounting firm for fiscal year 2018.

 B Non-Voting Items

Change of Address— Please print your new address below.

Comments — Please print your comments below.Meeting Attendance
Mark the box to the right if you plan to attend the Annual Meeting.

     

 C  Authorized Signatures — This section must be completed for your vote to be counted. — Date and Sign Below 

Please sign exactly as name(s) appears hereon. Joint owners should each sign. When signing as attorney, executor, administrator, corporate officer, trustee, guardian, or custodian, please give full title.

Date (mm/dd/yyyy) — Please print date below. Signature [PLEASE SIGN WITHIN BOX]Date    Signature (Joint Owners)Date  1 — Please keep signature within the box. Signature 2 — Please keep signature within the box.

                /                /


LOGO

2018 Annual Meeting Admission Ticket

2018 Annual Meeting of

Heritage Insurance Holdings, Inc. Stockholders

Friday, June 22, 2018, 10:00 a.m., ET

The Grand Hyatt Tampa Bay

2900 Bayport Dr.

Tampa, Florida 33607

Upon arrival, please present this admission ticket

and photo identification at the registration desk.

q IF YOU HAVE NOT VOTED VIA THE INTERNETOR TELEPHONE, FOLD ALONG THE PERFORATION,

DETACH AND RETURN THE BOTTOM PORTION IN THE ENCLOSED ENVELOPE.q

 

 

 

LOGO

THIS PROXY IS SOLICITED ON BEHALF OF THE BOARD OF

DIRECTORS OF

HERITAGE INSURANCE HOLDINGS, INC.

Special

Proxy — Heritage Insurance Holdings, Inc.

Notice of 2018 Annual Meeting of Stockholders on December 1, 2017

The undersigned, revoking all prior proxies, hereby constitutes and appoints Grand Hyatt Tampa Bay, 2900 Bayport Dr., Tampa, Florida 33607

Proxy Solicited by Board of Directors for Annual Meeting – June 22, 2018

Bruce Lucas, Richard Widdicombe and Steven Martindale, his true and lawful agent and proxyErnie Garateix, or any of them, each with fullthe power of substitution, in each,are hereby authorized to attendrepresent and vote the Specialshares of the undersigned, with all the powers which the undersigned would possess if personally present, at the Annual Meeting of Stockholders of Heritage Insurance Holdings, Inc. to be held at, 2600 McCormick Drive, Suite 300, Clearwater, Florida 33759 at 10:00 a.m., Eastern Time, on December 1, 2017, andJune 22, 2018 or at any adjournmentspostponement or postponements thereof,adjournment thereof.

Shares represented by this proxy will be voted by the stockholder. If no such directions are indicated, the Proxies will have authority to cast on behalfvote FOR each of the undersigned all votes thatdirector nominees and FOR the undersigned is entitledratification of Grant Thornton LLP as the independent registered public accounting firm for fiscal year 2018.

In their discretion, the Proxies are authorized to cast atvote upon such meeting, and otherwise representother business as may properly come before the undersigned at the meeting with all powers possessed by the undersigned if personally present at the meeting. THE VOTES ENTITLED TO BE CAST BY THE UNDERSIGNED WILL BE CAST AS INSTRUCTED ON THE REVERSE SIDE HEREOF. IF THIS PROXY IS EXECUTED BUT NO INSTRUCTION IS GIVEN, THE VOTES ENTITLED TO BE CAST BY THE UNDERSIGNED WILL BE CAST “FOR” PROPOSALS 1 AND 2. THIS PROXY WILL BE VOTED IN THE DISCRETION OF THE PROXY HOLDER ON ANY OTHER MATTER THAT MAY PROPERLY COME BEFORE THE MEETING OR ANY ADJOURNMENTS OR POSTPONEMENTS THEREOF.

Continued and(Items to be signedvoted appear on reverse side

side.)

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