UNITED STATES

SECURITIES AND EXCHANGE COMMISSION

Washington, DC 20549

SCHEDULE 14A

(RULE 14a-101)

Proxy Statement Pursuant to Section 14(a) of the

Securities Exchange Act of 1934

Filed by the Registrant  ☒

Filed by a Party other than the Registrant  ☐

Check the appropriate box:

BOTTOMLINE TECHNOLOGIES, INC.

(Name of Registrant as Specified In Its Charter)

N/A

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

Payment of Filing Fee (Check the appropriate box)all boxes that apply):

PRELIMINARY PROXY STATEMENT — SUBJECT TO COMPLETION

Bottomline Technologies, Inc.

325 Corporate Drive

Portsmouth, New Hampshire 03801

[●],February 2, 2022

To the Stockholders of Bottomline Technologies, Inc.:

You are cordially invited to attend a special meeting of stockholders (the “Special Meeting”) of Bottomline Technologies, Inc., a Delaware corporation (“Bottomline”, the “Company”, “we”, “us” or “our”) to be held on [●],March 8, 2022, at [●]4 p.m., Eastern time,Time, at [●].325 Corporate Drive, Portsmouth, NH 03801.

At the Special Meeting, you will be asked to consider and vote on a proposal to adopt the Agreement and Plan of Merger (as it may be amended from time to time, the “Merger Agreement”), dated December 16, 2021, by and among Bottomline, Bottomline Intermediate Holdings III, LLC (formerly known as Project RB Parent, LLC), a Delaware limited liability company (“Parent”), and Project RB Merger Sub, Inc., a Delaware corporation (“Merger Sub”). Parent and Merger Sub are affiliates of Thoma Bravo Fund XV, L.P. (the “Thoma Bravo Fund”), a private equity fund managed by Thoma Bravo, L.P. (“Thoma Bravo”). Pursuant to the terms of the Merger Agreement, Merger Sub will merge with and into Bottomline (the “Merger”), and Bottomline will become a wholly owned subsidiary of Parent. At the Special Meeting, you will also be asked to consider and vote on a non-binding, advisory proposal to approve compensation that will or may become payable by Bottomline to its named executive officers in connection with the Merger.

If the Merger is completed, you will be entitled to receive $57.00 in cash, without interest and less any applicable withholding taxes, for each share of common stock that you own (unless you have properly exercised your appraisal rights under Section 262 of the Delaware General Corporation Law (“DGCL”)), which represents a premium of: (1) approximately 41% and 40% to the unaffected 30-day and 60-day (respectively) volume weighted average price of Bottomline’s common stock prior to October 19, 2021, the last trading day prior to the announcement of the appointment of Michael Curran, Philip Hilal and Larry Klane to the board of directors of Bottomline (the “Board of Directors”); and (2) approximately 13% to the closing price of Bottomline’s common stock on December 15, 2021, the last trading day prior to the date on which Bottomline entered into the Merger Agreement.

The Board of Directors, after considering the factors more fully described in the enclosed proxy statement, has unanimously (1) adopted and declared advisable the Merger Agreement and the transactions contemplated by the Merger Agreement; (2) declared that it is in the best interests of Bottomline and its stockholders that Bottomline enter into the Merger Agreement and consummate the transactions contemplated by the Merger Agreement, in each case on the terms and subject to the conditions set forth in the Merger Agreement; and (3) declared that the terms of the Merger Agreement are fair to Bottomline and its stockholders. The Board of Directors unanimously recommends that you vote (1) “FOR” the adoption of the Merger Agreement; (2) “FOR” the adjournment of the Special Meeting, if necessary or appropriate, to solicit additional proxies if there are insufficient votes to adopt the Merger Agreement at the time of the Special Meeting; and (3) “FOR” the proposal to approve, by non-binding, advisory vote, compensation that will or may become payable by Bottomline to its named executive officers in connection with the Merger.

The enclosed proxy statement provides detailed information about the Special Meeting, the Merger Agreement and the Merger. A copy of the Merger Agreement is attached as Annex A to the proxy statement. The proxy statement also describes the actions and determinations of the Board of Directors in connection with its evaluation of the Merger Agreement and the Merger. We encourage you to read the proxy statement and its annexes, including the Merger Agreement, carefully and in their entirety, as they contain important information.

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over the Internet or by telephone. If you attend the Special Meeting and vote in person by ballot, your vote will revoke any proxy that you have previously submitted.

If you hold your shares in “street name,” you should instruct your bank, broker or other nominee how to vote your shares in accordance with the voting instruction form that you will receive from your bank, broker or other nominee. Your bank, broker or other nominee cannot vote on any of the proposals, including the proposal to adopt the Merger Agreement, without your instructions.

Your vote is very important, regardless of the number of shares that you own. We cannot complete the Merger unless the proposal to adopt the Merger Agreement is approved by the affirmative vote of the holders of at least a majority of the outstanding shares of Bottomline common stock.

If you have any questions or need assistance voting your shares, please contact our Proxy Solicitor:

Innisfree M&A Incorporated

Stockholders May Call Toll-Free: (877) 687-1865

Banks & Brokers May Call Collect: (212) 750-5833

On behalf of the Board of Directors, I thank you for your support and appreciate your consideration of this matter.

Sincerely,

[signature]/s/ Joseph L. Mullen                

Joseph L. Mullen

Chairman of the Board of Directors

The accompanying proxy statement is dated [●],February 2, 2022 and, together with the enclosed form of proxy card, is first being mailed on or about [●],February 7, 2022.

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PRELIMINARY PROXY STATEMENT — SUBJECT TO COMPLETION

Bottomline Technologies, Inc.

325 Corporate Drive

Portsmouth, New Hampshire 03801

NOTICE OF SPECIAL MEETING OF STOCKHOLDERS

TO BE HELD ON [●],MARCH 8, 2022

Notice is hereby given that a special meeting of stockholders (the “Special Meeting”) of Bottomline Technologies, Inc., a Delaware corporation (“Bottomline”, the “Company”, “we”, “us” or “our”), will be held on [●],March 8, 2022, at [●], at [●]4 p.m., Eastern time,Time, at [●],325 Corporate Drive, Portsmouth, NH 03801, for the following purposes:

Only stockholders of record as of the close of business on [●],February 1, 2022 are entitled to notice of the Special Meeting and to vote at the Special Meeting or any adjournment, postponement or other delay thereof.

The Board of Directors unanimously recommends that you vote (1) “FOR” the adoption of the Merger Agreement; (2) “FOR” the adjournment of the Special Meeting, if necessary or appropriate, to solicit additional proxies if there are insufficient votes to adopt the Merger Agreement at the time of the Special Meeting; and (3) “FOR” the proposal to approve, by non-binding, advisory vote, compensation that will or may become payable by Bottomline to its named executive officers in connection with the Merger.

Whether or not you plan to attend the Special Meeting in person, please sign, date and return, as promptly as possible, the enclosed proxy card in the accompanying prepaid reply envelope or grant your proxy electronically over the Internet or by telephone. If you attend the Special Meeting and vote in person by ballot, your vote will revoke any proxy that you have previously submitted. If you hold your shares in “street name,” you should instruct your bank, broker or other nominee how to vote your shares in accordance with the voting instruction form that you will receive from your bank, broker or other nominee. Your bank, broker or other nominee cannot vote on any of the proposals, including the proposal to adopt the Merger Agreement, without your instructions.

By the Order of the Board of Directors,

[signature]/s/ A. Bruce Bowden            

A. Bruce Bowden

Chief Financial Officer

Dated: [●],February 2, 2022

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YOUR VOTE IS IMPORTANT

WHETHER OR NOT YOU PLAN TO ATTEND THE SPECIAL MEETING IN PERSON, WE ENCOURAGE YOU TO SUBMIT YOUR PROXY AS PROMPTLY AS POSSIBLE (1) BY TELEPHONE; (2) THROUGH THE INTERNET; OR (3) BY SIGNING AND DATING THE ENCLOSED PROXY CARD AND RETURNING IT IN THE POSTAGE-PAID ENVELOPE PROVIDED. You may revoke your proxy or change your vote at any time before it is voted at the Special Meeting.

If you hold your shares in “street name,” you should instruct your bank, broker or other nominee how to vote your shares in accordance with the voting instruction form that you will receive from your bank, broker or other nominee. Your broker or other agent cannot vote on any of the proposals, including the proposal to adopt the Merger Agreement, without your instructions.

If you are a stockholder of record, voting in person by ballot at the Special Meeting will revoke any proxy that you previously submitted. If you hold your shares through a bank, broker or other nominee, you must obtain a “legal proxy” in order to vote in person at the Special Meeting.

If you fail to (1) return your proxy card; (2) grant your proxy electronically over the Internet or by telephone; or (3) attend the Special Meeting in person, your shares will not be counted for purposes of determining whether a quorum is present at the Special Meeting and, if a quorum is present, will have the same effect as a vote “AGAINST” the proposal to adopt the Merger Agreement but will have no effect on the other two proposals.

We encourage you to read the accompanying proxy statement and its annexes, including all documents incorporated by reference into the accompanying proxy statement, carefully and in their entirety. If you have any questions concerning the Merger, the Special Meeting or this proxy statement, would like additional copies of this proxy statement or need help voting your shares of common stock, please contact our Proxy Solicitor:

Innisfree M&A Incorporated

Stockholders May Call Toll-Free: (877) 687-1865

Banks & Brokers May Call Collect: (212) 750-5833

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TABLE OF CONTENTS

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PRELIMINARY PROXY STATEMENT — SUBJECT TO COMPLETION

SUMMARY

This summary highlights selected information from this proxy statement related to the merger of Project RB Merger Sub, Inc. with and into Bottomline Technologies, Inc., which we refer to as the “Merger”, and may not contain all of the information that is important to you. To understand the Merger more fully and for a more complete description of the legal terms of the Merger, you should carefully read this entire proxy statement, the annexes to this proxy statement and the documents that we refer to in this proxy statement. You may obtain the information incorporated by reference in this proxy statement without charge by following the instructions under the caption “Where You Can Find More Information.” The Merger Agreement is attached as Annex A to this proxy statement. We encourage you to read the Merger Agreement, which is the legal document that governs the Merger, carefully and in its entirety.

Except as otherwise specifically noted in this proxy statement, “Bottomline”, the “Company”, “we”, “our”, “us” and similar words refer to Bottomline Technologies, Inc., including, in certain cases, our subsidiaries. Throughout this proxy statement, we refer to Bottomline Intermediate Holdings III, LLC (formerly known as Project RB Parent, LLC) as “Parent” and Project RB Merger Sub, Inc. as “Merger Sub”. In addition, throughout this proxy statement we refer to the Agreement and Plan of Merger, dated December 16, 2021, by and among Bottomline, Parent and Merger Sub, as it may be amended from time to time, as the “Merger Agreement”.

Parties Involved in the Merger

Bottomline Technologies, Inc.

Bottomline makes complex business payments simple, smart and secure. Corporations and banks rely on Bottomline for domestic and international payments, efficient cash management, automated workflows for payment processing and bill review, and fraud detection, behavioral analytics and regulatory compliance solutions. Thousands of corporations around the world benefit from Bottomline solutions. Headquartered in Portsmouth, NH, Bottomline delights customers through offices across the U.S., Europe and Asia-Pacific.

Bottomline’s common stock is listed on The NASDAQ Global Select Market (“NASDAQ”) under the symbol “EPAY”.

Bottomline Intermediate Holdings III, LLC (formerly known as Project RB Parent, LLC)

Bottomline Intermediate Holdings III, LLC (formerly known as Project RB Parent, LLC) was formed on December 9, 2021, solely for the purpose of engaging in the transactions contemplated by the Merger Agreement and has not engaged in any business activities other than in connection with the transactions contemplated by the Merger Agreement and arranging the equity financing and debt financing, if applicable, in connection with the Merger.

Project RB Merger Sub Inc.

Project RB Merger Sub, Inc. is a wholly owned direct subsidiary of Parent and was formed on December 9, 2021, solely for the purpose of engaging in the transactions contemplated by the Merger Agreement and has not engaged in any business activities other than in connection with the transactions contemplated by the Merger Agreement and arranging the equity financing and debt financing, if applicable, in connection with the Merger.

Parent and Merger Sub are each affiliated with Thoma Bravo Fund XV, L.P. (the “Thoma Bravo Fund”). In connection with the transactions contemplated by the Merger Agreement, the Thoma Bravo Fund has provided to Parent an equity commitment of an amount equal to the estimated amount of aggregate consideration that will be due and payable at closing.

The Thoma Bravo Fund is managed by Thoma Bravo, L.P. (“Thoma Bravo”Bravo”). Thoma Bravo is a leading private equity investment firm building on a 30+ year history of providing equity and strategic support to experienced management teams and growing companies.

For more information, please see the section captioned “The Merger — Parties Involved in the Merger.” beginning on page 3031 of this proxy statement.

The Merger

Upon the terms and subject to the conditions of the Merger Agreement, if the Merger is completed, Merger Sub will merge with and into Bottomline, and Bottomline will continue as the surviving corporation and as a wholly owned subsidiary of Parent (the “Surviving Corporation”). As a result of the Merger, Bottomline will cease to be a publicly traded company, all outstanding shares of Bottomline stock will be canceled and converted into the right to receive $57.00 per share in cash, less any applicable withholding taxes (the “Per Share Merger Consideration”) (except for any shares owned by Parent or Merger Sub or stockholders who are entitled to and who properly exercise appraisal rights pursuant to Section 262 of the Delaware General Corporation Law (the “DGCL”)), and you will not own any shares of the capital stock of the Surviving Corporation.

After the Merger is completed, you will have the right to receive the Per Share Merger Consideration, but you will no longer have any rights as a stockholder (except that stockholders who properly exercise their appraisal rights will have the right to receive a payment for the “fair value” of their shares as determined pursuant to an appraisal proceeding as contemplated by Section 262 of the DGCL, as described below under the caption “The Merger — Appraisal Rights”).

For more information, see the section of this proxy statement captioned “The Merger” beginning on page 3031 of this proxy statement.

Treatment of Restricted Stock Awards, Restricted Stock Unit Awards and Stock Options

Each restricted stock award, restricted stock unit award and stock option award that is outstanding as of the time the Merger becomes effective (the “Effective Time”) will be provided at that time with an additional 30 months of time-based vesting credit (measured from the closing date) (the “Additional Vesting Credit”), which includes the additional 12 months of time-based vesting credit provided under the Company’s 2019 Stock Incentive Plan (as amended) in connection with a “change in control” (which will occur upon the Effective Time), unless a holder is entitled to alternative vesting provisions under an existing award agreement or contract. In addition, any performance-based vesting conditions under restricted stock awards and restricted stock unit awards that are outstanding as of the Effective Time will be deemed to have been achieved at the target level of performance. Additional “double-trigger” vesting protection applies for remaining unvested awards (i.e., awards that remain unvested following application of the Additional Vesting Credit) in the event of a qualifying termination of employment following the Effective Time.

After giving effect to the Additional Vesting Credit, all vested restricted stock awards, vested restricted stock unit awards and vested stock options will be cancelled at the Effective Time and converted into the right to receive the Per Share Merger Consideration with respect to each share of Bottomline common stock subject to the award (less applicable withholding and any applicable exercise price in the case of stock options) promptly following the Effective Time. Restricted stock awards and restricted stock unit awards which remain unvested as of the Effective Time (after application of the Additional Vesting Credit) will be converted into the right to receive an amount in cash equal to the Per Share Merger Consideration (less applicable withholding) multiplied by the number of shares of Bottomline stock subject to the award, which amount will be payable by the Surviving Corporation upon vesting, subject to the holder’s continued service with the Surviving Corporation. The Additional Vesting Credit will be applied for purposes of determining the timing of vesting and payment of the replacement cash amounts issued in respect of restricted stock awards and restricted stock unit awards that

remain unvested as of the Effective Time after the application of such Additional Vesting Credit. It is anticipated that all of the Company’s stock options will be vested as of the Effective Time and that all of the Company’s stock options will have an exercise price less than the Per Share Merger Consideration.

For more information, please see the section captioned “The Merger Agreement — Interests of Bottomline’s Directors and Executive Officers in the Merger.” beginning on page 55 of this proxy statement.

Financing of the Merger

We anticipate that the total funds needed to complete the Merger will be approximately $2.6 billion, which will be funded via the equity financing described below. This amount includes funds needed to (i) pay our stockholders the amounts due to them under the Merger Agreement, (ii) pay all fees and expenses payable by Parent and Merger Sub under the Merger Agreement and (iii) make payments due as of the Effective Time in respect of our outstanding equity-based awards pursuant to the Merger Agreement.

In connection with the Merger, Parent has entered into an equity commitment letter, dated as of December 16, 2021, with the Thoma Bravo Fund (the “Equity Commitment Letter”), to which Bottomline is an express limited third party beneficiary, for an amount equal to the estimated amount of aggregate consideration that will be due and payable at closing (the “Equity Financing”). For more information, see the section of this proxy statement captioned “The Merger — Financing of the Merger,” beginning on page 63 of this proxy statement.

Under the Merger Agreement, Bottomline has agreed to cooperate should Parent attempt to obtain any debt financing for the purpose of funding the transactions contemplated by the Merger Agreement (the “Debt Financing”). For more information, please see the section captioned “The Merger Agreement — Financing Cooperation,” beginning on page 8889 of this proxy statement.

Conditions to the Closing of the Merger

The obligations of Bottomline, Parent and Merger Sub, as applicable, to consummate the Merger are subject to the satisfaction or waiver of certain conditions, including (among other conditions), the following:

For more information, please see the section captioned “The Merger Agreement — Conditions to the Closing of the Merger,” beginning on page 9394 of this proxy statement.

Regulatory Approvals Required for the Merger

Bottomline and Parent have agreed to use their reasonable best efforts to comply with all regulatory notification requirements and obtain all regulatory approvals required to consummate the Merger and the other transactions contemplated by the Merger Agreement. These approvals include (i) the expiration or early termination of the applicable waiting period under the HSR Act; and (ii) approval of the change in control relating to Bottomline Payment Services Limited (a U.K. based subsidiary of Bottomline) by the FCA.

Bottomline and Parent made the necessary filings with the Federal Trade Commission (the “FTC”) and the Antitrust Division of the DOJ (the “DOJ”) on December 30, 2021. The required waiting period under the HSR Act with respect to the Merger expired at 11:59 p.m., Eastern Time on January 31, 2022. Accordingly, the condition of the expiration or termination of the applicable waiting period under the HSR Act as described below under the caption “— Conditions to the Closing of the Merger” has been satisfied. Additionally, Parent submitted a change in control application with the FCA on January 20, 2022.

For more information, please see the section captioned “The Merger — Regulatory Approvals Required for the Merger,” beginning on page 71 of this proxy statement.

Recommendation of the Board of Directors

Bottomline’s Board of Directors (the “Board of Directors”), after considering various factors described under the caption “The Merger — Recommendation of the Board of Directors and Reasons for the Merger,” has unanimously (1) adopted and declared advisable the Merger Agreement and the transactions contemplated by the Merger Agreement, (2) declared that it is in the best interests of Bottomline and its stockholders that Bottomline enter into the Merger Agreement and consummate the transactions contemplated by the Merger Agreement, in each case on the terms and subject to the conditions set forth in the Merger Agreement and (3) declared that the terms of the Merger Agreement are fair to Bottomline and its stockholders. The Board of Directors unanimously recommends that you vote (1) “FOR” the adoption of the Merger Agreement; (2) “FOR” the adjournment of the Special Meeting, if necessary or appropriate, to solicit additional proxies if there are insufficient votes to adopt the Merger Agreement at the time of the Special Meeting; and (3) “FOR” the proposal to approve, by non-binding, advisory vote, compensation that will or may become payable by Bottomline to its named executive officers in connection with the Merger.

Opinion of Bottomline’s Financial Advisor

In connection with the Merger Agreement and the Merger, Deutsche Bank Securities Inc. (which we refer to as “Deutsche Bank”) on December 16, 2021, delivered its oral opinion to the Board, subsequently confirmed in a written opinion dated December 17, 2021, that, as of such date and based upon and subject to the assumptions, limitations, qualifications and other conditions set forth in the opinion, the Per Share Merger Consideration was fair, from a financial point of view, to holders of Bottomline’s common stock.

The full text of Deutsche Bank’s written opinion, dated as of December 17, 2021, which sets forth, among other things, the assumptions made, matters considered and limitations, qualifications and conditions of the review undertaken by Deutsche Bank in connection with its opinion, is attached as Annex B to this proxy statement and is incorporated herein by reference. The summary of Deutsche Bank’s opinion set forth in this proxy statement is

qualified in its entirety by reference to the full text of Deutsche Bank’s opinion set forth as Annex B. Deutsche Bank’s opinion was addressed to, and for the use and benefit of, the Board of Directors in connection with and for purposes of its evaluation of the Merger. For more information regarding the opinion of Deutsche Bank, see “The Merger — Opinion of Bottomline’s Financial Advisor” beginning on page 4647 of this proxy statement. Deutsche Bank’s opinion is not a recommendation as to how any holders of shares should vote with respect to the Merger.

C and incorporated herein by reference. The following summary does not constitute any legal or other advice and does not constitute a recommendation that stockholders exercise their appraisal rights under Section 262. Only a holder of record of shares of common stock is entitled to demand appraisal rights for the shares registered in that holder’s name. A person having a beneficial interest in shares of common stock held of record in the name of another person, such as a bank, broker or other nominee, must act promptly to cause the record holder to follow the steps summarized below properly and in a timely manner to perfect appraisal rights. If you hold your shares

A Non-U.S. Holder (as defined under the caption “The Merger — U.S. Federal Income Tax Consequences of the Merger”) generally will not be subject to U.S. federal income tax with respect to the exchange of common stock for cash in the Merger unless such Non-U.S. Holder has certain connections to the United States.

and their respective directors, officers, managers, employees, consultants, legal counsel, financial advisors and agents and other representatives, whom we collectively refer to as “representatives,”) not to, directly or indirectly, among other things:

Notwithstanding these restrictions, under certain circumstances, prior to the adoption of the Merger Agreement by Bottomline’s stockholders, Bottomline may provide information to and afford access to the business, employees, officers, contracts, properties, assets, books and records of Bottomline and its subsidiaries to, and engage or participate in negotiations or discussions with, a person regarding an Acquisition Proposal if the Board of Directors determines in good faith after consultation with its financial advisor and its outside legal counsel that such proposal is a Superior Proposal (as defined in the section below captioned “The Merger Agreement — Acquisition Proposals”) or could reasonably be expected to lead to a Superior Proposal and not to do so would be inconsistent with the directors’ exercise of their fiduciary duties under applicable law. For more information, see the section of this proxy statement captioned “The Merger Agreement — Acquisition Proposals,” beginning on page 8283 of this proxy statement.

Company Board Recommendation Change

The Board of Directors has unanimously recommended that you vote “FOR” the adoption of the Merger Agreement. The Merger Agreement provides that the Board of Directors may not change its recommendation, or take other actions constituting a Company Board Recommendation Change, except in certain specified circumstances. For more information, see the section of this proxy statement captioned “The Merger Agreement — The Board of Directors’ Recommendation; Company Board Recommendation Change,” beginning on page 8586 of this proxy statement.

For more information, please see the section captioned “The Merger Agreement — Termination of the Merger Agreement,” beginning on page 9596 of this proxy statement.

Termination Fees and Expense Reimbursement

Except in specified circumstances, whether or not the Merger is completed, Bottomline, on the one hand, and Parent and Merger Sub, on the other hand, are each responsible for all of their respective costs and expenses incurred in connection with the Merger and the other transactions contemplated by the Merger Agreement.

Bottomline will be required to pay to Parent a termination fee of $78,000,000 if the Merger Agreement is terminated under specified circumstances. In addition, in certain circumstances, Bottomline will be required to reimburse Parent for up to $5,000,000 of its expenses associated with the transactions contemplated by the Merger Agreement (with such reimbursement deducted from the termination fee, should it not be payable at the time of such termination but subsequently become payable).

For more information on these termination fees, see the section of this proxy statement captioned “The Merger Agreement — Termination Fees and Expense Reimbursement,” beginning on page 9798 of this proxy statement.

Effect on Bottomline if the Merger is Not Completed

If the Merger Agreement is not adopted by Bottomline’s stockholders or if the Merger is not completed for any other reason, stockholders will not receive any payment for their shares of common stock. Instead, Bottomline will remain an independent public company, our common stock will continue to be listed and traded on NASDAQ and registered under the Securities Exchange Act of 1934 (“Exchange Act”), and we will continue to file periodic reports with the SEC. Under specified circumstances, Bottomline will be required to pay Parent a termination fee upon the termination of the Merger Agreement. For more details see the section of this proxy statement captioned “The Merger Agreement — Termination Fees and Expense Reimbursement,” beginning on page 9798 of this proxy statement.

The Special Meeting

Date, Time and Place

A special meeting of stockholders of Bottomline (the “Special Meeting”) will be held on [●],March 8, 2022, at [●]4 p.m., Eastern time,Time, at [●].325 Corporate Drive, Portsmouth, NH 03801.

Record Date; Shares Entitled to Vote

You are entitled to vote at the Special Meeting if you owned shares of common stock at the close of business on [●]February 1, 2022 (the “Record Date”). You will have one vote at the Special Meeting for each share of common stock that you owned at the close of business on the Record Date.

Required Vote

The affirmative vote of the holders of a majority of the outstanding shares of Bottomline common stock is required to adopt the Merger Agreement. Approval of the proposal to adjourn the Special Meeting, requires the affirmative vote of a majority of the shares of stock having voting power present in person or represented by proxy at the Special Meeting and entitled to vote on the subject matter. Approval, by non-binding, advisory vote, of compensation that will or may become payable to Bottomline’s executive officers in connection with the Merger requires the affirmative vote of a majority of the shares of stock having voting power present in person or represented by proxy at the Special Meeting entitled to vote on the subject matter.

Share Ownership of Our Directors and Executive Officers; Voting Agreement

As of the Record Date,January 24, 2022, our directors and executive officers beneficially owned and were entitled to vote, in the aggregate, [●]2,102,381 shares of common stock, representing approximately [●]%4.7% of the shares of common stock outstanding on the Record Date.January 24, 2022.

Parent and Bottomline have entered into a voting agreement (the “Voting Agreement”) with our directors (including our chief executive officer) and Clearfield Capital Management LP (collectively, the “Supporting Shareholders”), which collectively hold approximately 4% of the outstanding shares of our common stock.stock, as of the date of the Voting Agreement. A copy of the Voting Agreement is attached as Annex D and is incorporated herein by reference. Under the Voting Agreement, the Supporting Shareholders agree, among other things, during the term of the Voting Agreement, to vote their shares of common stock (i) in favor of the adoption of Merger Agreement and the approval of the transactions contemplated thereby and (ii) against any alternative acquisition proposal, and not to, directly or indirectly, sell, transfer, exchange or otherwise dispose of their shares, subject to certain limited exceptions.

We currently expect that our directors and executive officers will vote all of their respective shares of Bottomline common stock: (1) “FOR” the adoption of the Merger Agreement; (2) “FOR” the adjournment of the Special Meeting, if necessary or appropriate, to solicit additional proxies if there are insufficient votes to adopt the Merger Agreement at the time of the Special Meeting; and (3) “FOR” the non-binding, advisory proposal to approve compensation that will or may become payable by Bottomline to its named executive officers in connection with the Merger.

Voting and Proxies

Any stockholder of record entitled to vote may submit a proxy by returning a signed proxy card by mail in the accompanying prepaid reply envelope or granting a proxy electronically over the Internet or by telephone, or may vote in person by appearing at the Special Meeting. If you are a beneficial owner and hold your shares of common stock in “street name” through a bank, broker or other nominee, you should instruct your bank, broker

If you hold your shares of common stock in “street name,” you should contact your bank, broker or other nominee for instructions regarding how to change your vote. You may also vote in person at the Special Meeting if you obtain a “legal proxy” from your bank, broker or other nominee.

For more information, see the section of this proxy statement captioned “The Special Meeting” beginning on page 2223 of this proxy statement.

QUESTIONS AND ANSWERS

The following questions and answers address some commonly asked questions regarding the Merger, the Merger Agreement and the Special Meeting. These questions and answers may not address all questions that are important to you. We encourage you to read carefully the more detailed information contained elsewhere in this proxy statement, the annexes to this proxy statement and the documents we refer to in this proxy statement. You may obtain the information incorporated by reference in this proxy statement without charge by following the instructions under the caption “Where You Can Find More Information.”

A:    The Board of Directors is furnishing this proxy statement and form of proxy card to the holders of shares of Bottomline common stock in connection with the solicitation of proxies to be voted at the Special Meeting.

A:    You are being asked to vote on the following proposals:

1) To adopt the Merger Agreement pursuant to which Merger Sub will merge with and into Bottomline, and Bottomline will become a wholly owned subsidiary of Parent;

2) To approve the adjournment of the Special Meeting to a later date or dates, if necessary or appropriate, to solicit additional proxies if there are insufficient votes to adopt the Merger Agreement at the time of the Special Meeting; and

3) To approve, by non-binding, advisory vote, compensation that will or may become payable by Bottomline to its named executive officers in connection with the Merger.

A:    The Special Meeting will take place on [●],March 8, 2022, at [●]4 p.m., Eastern time,Time, at [●].325 Corporate Drive, Portsmouth, NH 03801.

A:    Stockholders as of the Record Date are entitled to notice of the Special Meeting and to vote at the Special Meeting (and at any adjournment or postponement thereof). Each holder of shares of Bottomline common stock is entitled to cast one vote on each matter properly brought before the Special Meeting for each share of common stock owned as of the Record Date.

A:    Yes. All stockholders as of the Record Date may attend the Special Meeting and vote in person. Seating will be limited. Stockholders will need to present proof of ownership of shares of Bottomline common stock, such as a bank or brokerage account statement, and a form of personal identification to be admitted to the Special Meeting. No cameras, recording equipment, electronic devices, large bags, briefcases or packages will be permitted in the Special Meeting. Due to health and safety considerations related to COVID-19, in-person attendance will require compliance with any then-applicable governmental requirements or recommendations as well as with facility requirements.

Even if you plan to attend the Special Meeting in person, to ensure that your shares will be represented at the Special Meeting we encourage you to sign, date and return the enclosed proxy card in the accompanying prepaid reply envelope or grant your proxy electronically over the Internet or by telephone. If you attend the Special Meeting and vote in person by ballot, your vote will revoke any proxy previously submitted.

If you hold your shares in “street name,” you should instruct your bank, broker or other nominee how to vote your shares in accordance with the voting instruction form that you will receive from your bank, broker or other

nominee. Your broker or other agent cannot vote on any of the proposals, including the proposal to adopt the Merger Agreement, without your instructions. If you hold your shares in “street name,” you may not vote your shares in person at the Special Meeting unless you obtain a “legal proxy” from your bank, broker or other nominee.

A:    Although we are currently planning to hold the Special Meeting in person, in light of the ongoing public health concerns surrounding the COVID-19 pandemic, we are planning for the possibility that the Special Meeting may be held solely by means of remote communication (i.e., a virtual-only meeting) in lieu of an in-person meeting. If we decide to hold a virtual Special Meeting, we will publicly announce the decision in advance in a press release, and details on how to access the virtual Special Meeting will be posted on our website at investors.bottomline.comwww.investors.bottomline.com as soon as practicable before the Special Meeting and filed as additional proxy soliciting material with the SEC. In that event, the Special Meeting will be held on the above date and time but would be available via live video webcast. We recommend that you monitor our website for updated information, and please check the website in advance of the Special Meeting to confirm the status of the Special Meeting before planning to attend in person.

A:    The proposed Merger is the acquisition of Bottomline by Parent. If the proposal to adopt the Merger Agreement is approved by Bottomline’s stockholders and the other closing conditions under the Merger Agreement have been satisfied or waived, Merger Sub will merge with and into Bottomline, with Bottomline continuing as the Surviving Corporation. As a result of the Merger, Bottomline will become a wholly owned subsidiary of Parent, and our common stock will no longer be publicly traded and will be delisted from NASDAQ. In addition, our common stock will be deregistered under the Exchange Act, and we will no longer file periodic reports with the SEC.

A:    Upon completion of the Merger, you will be entitled to receive the Per Share Merger Consideration for each share of Bottomline common stock that you own, unless you have properly exercised and not withdrawn your appraisal rights under the DGCL. For example, if you own 100 shares of common stock, you will receive $5,700.00 in cash in exchange for your shares of common stock, less any applicable withholding taxes.

A:    The $57.00 Per Share Merger Consideration constituted a premium of: (1) approximately 41% and 40% to the unaffected 30-day and 60-day (respectively) volume weighted average price of Bottomline’s common stock prior to October 19, 2021, the last trading day prior to the announcement of the appointment of Michael Curran, Philip Hilal and Larry Klane to the Board of Directors; and (2) approximately 13% to the closing price of Bottomline’s common stock on December 15, 2021, the last trading day prior to the date on which Bottomline entered into the Merger Agreement.

A:    We encourage you to read this proxy statement, the annexes to this proxy statement and the documents that we refer to in this proxy statement carefully and consider how the Merger affects you. Then sign, date and return, as promptly as possible, the enclosed proxy card in the accompanying reply envelope, or grant your proxy electronically over the Internet or by telephone, so that your shares can be voted at the Special Meeting, unless you wish to seek appraisal. If you hold your shares in “street name,” please refer to the voting instruction forms provided by your bank, broker or other nominee to vote your shares. Please do not send your stock certificates with your proxy card.

A:    No. After the Merger is completed, you will receive a letter of transmittal containing instructions for how to send your Bottomline stock certificates to the paying agent in order to receive the appropriate cash payment for the shares of common stock represented by your stock certificates. You should use the letter of transmittal to exchange your stock certificates for the cash payment to which you are entitled. Please do not send your stock certificates with your proxy card.

A:    The Record Date for the Special Meeting is earlier than the date of the Special Meeting and the date the Merger is expected to be completed. If you sell or transfer your shares of Bottomline common stock after the Record Date but before the Special Meeting, unless special arrangements (such as provision of a proxy) are made between you and the person to whom you sell or otherwise transfer your shares and each of you notifies Bottomline in writing of such special arrangements, you will transfer the right to receive the Per Share Merger Consideration, if the Merger is completed, to the person to whom you sell or transfer your shares, but you will retain your right to vote those shares at the Special Meeting. Even if you sell or otherwise transfer your shares of common stock after the Record Date, we encourage you to sign, date and return the enclosed proxy card in the accompanying reply envelope or grant your proxy electronically over the Internet or by telephone.

A:    The Board of Directors, after considering the various factors described under the caption “The Merger — Recommendation of the Board of Directors and Reasons for the Merger,” has unanimously (1) adopted and declared advisable the merger agreement and the transactions contemplated by the merger agreement; (2) declared that it is in the best interests of Bottomline and its stockholders that Bottomline enter into the merger agreement and consummate the transactions contemplated by the merger agreement, in each case on the terms and subject to the conditions set forth in the merger agreement; and (3) declared that the terms of the merger agreement are fair to Bottomline and its stockholders. The Board of Directors unanimously recommends that you vote (1) “FOR” the adoption of the Merger Agreement; (2) “FOR” the adjournment of the Special Meeting, if necessary or appropriate, to solicit additional proxies if there are insufficient votes to adopt the Merger Agreement at the time of the Special Meeting; and (3) “FOR” the proposal to approve, by non-binding, advisory vote, compensation that will or may become payable by Bottomline to its named executive officers in connection with the Merger.

A:    If the Merger Agreement is not adopted by Bottomline’s stockholders or if the Merger is not completed for any other reason, stockholders will not receive any payment for their shares of Bottomline common stock. Instead, Bottomline will remain an independent public company, our common stock will continue to be listed and traded on NASDAQ and registered under the Exchange Act, and we will continue to file periodic reports with the SEC. Bottomline will be required to pay Parent a termination fee of $78,000,000 upon the termination of the Merger Agreement under specified circumstances, as described in the section captioned “The Merger Agreement — Termination Fees and Expense Reimbursement,” beginning on page 9798 of this proxy statement.

A:    The affirmative vote of the holders of a majority of the outstanding shares of Bottomline common stock is required to adopt the Merger Agreement. If a quorum is present at the Special Meeting, the failure of any stockholder of record to (1) submit a signed proxy card; (2) grant a proxy over the Internet or by telephone; or (3) vote in person by ballot at the Special Meeting will have the same effect as a vote “AGAINST” the proposal

to adopt the Merger Agreement. If you hold your shares in “street name” and a quorum is present at the Special Meeting, the failure to instruct your bank, broker or other nominee how to vote your shares will have the same effect as a vote “AGAINST” the proposal to adopt the Merger Agreement. If a quorum is present at the Special Meeting, abstentions will have the same effect as a vote “AGAINST” the proposal to adopt the Merger Agreement.

A:    Approval of the proposal to adjourn the Special Meeting requires the affirmative vote of a majority of the shares of stock having voting power present in person or represented by proxy at the Special Meeting and entitled to vote on the subject matter. Approval, by non-binding, advisory vote, of compensation that will or may become payable by Bottomline to its named executive officers in connection with the Merger requires the affirmative vote of a majority of the shares of stock having voting power present in person or represented by proxy at the Special Meeting and entitled to vote on the subject matter. The failure of any stockholder of record to (1) submit a signed proxy card; (2) grant a proxy over the Internet or by telephone; or (3) vote in person by ballot at the Special Meeting will not have any effect on the adjournment proposal or the proposal to approve, by non-binding, advisory vote, compensation that will or may become payable by Bottomline to its named executive officers in connection with the Merger. If you hold your shares in “street name,” the failure to instruct your bank, broker or other nominee how to vote your shares will not have any effect on the adjournment proposal and the proposal to approve, by non-binding, advisory vote, compensation that will or may become payable by Bottomline to its named executive officers in connection with the Merger. Abstentions will have the same effect as a vote “AGAINST” the adjournment proposal and the proposal to approve, by non-binding, advisory vote, compensation that will or may become payable by Bottomline to its named executive officers in connection with the Merger.

A:    SEC rules require Bottomline to seek a non-binding, advisory vote regarding compensation that will or may become payable by Bottomline to its named executive officers in connection with the Merger.

A:    The compensation that will or may become payable by Bottomline to its named executive officers in connection with the Merger is described more fully under the heading “Golden Parachute Compensation” beginning on page 60 of this proxy statement.

A:    Approval of the compensation that will or may become payable by Bottomline to its named executive officers in connection with the Merger is not a condition to completion of the Merger. The vote with respect to the compensation that will or may become payable by Bottomline to its named executive officers in connection with the Merger is an advisory vote and will not be binding on Bottomline or Parent. If the Merger Agreement is adopted by the stockholders and the Merger is completed, the compensation that will or may become payable by Bottomline to its named executive officers in connection with the Merger will or may be paid to Bottomline’s named executive officers pursuant to the terms of the applicable arrangement even if stockholders fail to approve such compensation.

A:    If your shares are registered directly in your name with our transfer agent, Computershare Trust Company, N.A., you are considered, with respect to those shares, to be the “stockholder of record.” In this case, this proxy statement and your proxy card have been sent directly to you by Bottomline.

If your shares are held through a bank, broker or other nominee, you are considered the “beneficial owner” of shares of common stock held in “street name.” In that case, this proxy statement has been forwarded to you by your bank, broker or other nominee who is considered, with respect to those shares, to be the stockholder of record. As the beneficial owner, you have the right to direct your bank, broker or other nominee how to vote your shares by following their instructions for voting. You are also invited to attend the Special Meeting. However, because you are not the stockholder of record, you may not vote your shares in person at the Special Meeting unless you obtain a “legal proxy” from your bank, broker or other nominee.

A:    If you are a stockholder of record (that is, if your shares of Bottomline common stock are registered in your name with Computershare Trust Company, N.A., our transfer agent), there are four ways to vote:

Even if you plan to attend the Special Meeting in person, you are strongly encouraged to vote your shares of Bottomline common stock by proxy. If you are a record holder or if you obtain a “legal proxy” to vote shares that you beneficially own, you may still vote your shares of Bottomline common stock in person by ballot at the Special Meeting even if you have previously voted by proxy. If you are present at the Special Meeting and vote in person by ballot, your previous vote by proxy will not be counted.

If your shares are held in “street name” through a bank, broker or other nominee, you may vote through your bank, broker or other nominee by completing and returning the voting form provided by your bank, broker or other nominee, or, if such a service is provided by your bank, broker or other nominee, electronically over the Internet or by telephone. To vote over the Internet or by telephone through your bank, broker or other nominee, you should follow the instructions on the voting form provided by your bank, broker or nominee.

A:    No. Your bank, broker or other nominee is permitted to vote your shares on any proposal currently scheduled to be considered at the Special Meeting only if you instruct your bank, broker or other nominee how to vote. You should follow the procedures provided by your bank, broker or other nominee to vote of your shares. Without instructions, your shares will not be voted on such proposals, which will have the same effect as if you voted against adoption of the Merger Agreement, but will have no effect on the adjournment proposal or the proposal to approve, by non-binding, advisory vote, compensation that will or may become payable by Bottomline to its named executive officers in connection with the Merger.

A:    Yes. If you are a stockholder of record, you may change your vote or revoke your proxy at any time before it is voted at the Special Meeting by:

A:    A proxy is your legal designation of another person, referred to as a “proxy,” to vote your shares of common stock. The written document describing the matters to be considered and voted on at the Special Meeting is called a “proxy statement.” The document used to designate a proxy to vote your shares of common stock is called a “proxy card.” Our Board of Directors has designated Joseph L. Mullen, our Chairman of the Board of Directors, Robert A. Eberle, our Chief Executive Officer, A. Bruce Bowden, our Chief Financial Officer, and each of them, with full power of substitution, as the proxy holders for the Special Meeting.

A:    Regardless of the method you choose to vote, the proxy holders will vote your shares in the way that you indicate. When completing the Internet or telephone process or the proxy card, you may specify whether your shares should be voted for or against or to abstain from voting on all, some or none of the specific items of business to come before the Special Meeting. If you properly sign your proxy card but do not mark the boxes showing how your shares should be voted on a matter, the shares represented by your properly signed proxy will be voted (1) “FOR” the adoption of the Merger Agreement; (2) “FOR” the adjournment of the Special Meeting, if necessary or appropriate, to solicit additional proxies if there are insufficient votes to adopt the Merger Agreement at the time of the Special Meeting; and (3) “FOR” the proposal to approve, by non-binding, advisory vote, compensation that will or may become payable by Bottomline to its named executive officers in connection with the Merger.

A:    You may receive more than one set of voting materials, including multiple copies of this proxy statement and multiple proxy cards or voting instruction cards. For example, if you hold your shares in more than one brokerage account, you will receive a separate voting instruction card for each brokerage account in which you hold shares. If you are a stockholder of record and your shares are registered in more than one name, you will receive more than one proxy card. Please sign, date and return (or grant your proxy electronically over the Internet or by telephone) each proxy card and voting instruction card that you receive.

A:    If available, Bottomline may announce preliminary voting results at the conclusion of the Special Meeting. Bottomline intends to publish final voting results in a Current Report on Form 8-K to be filed with the SEC following the Special Meeting. All reports that Bottomline files with the SEC are publicly available when filed. See the section of this proxy statement captioned “Where You Can Find More Information.” beginning on page 104105 of this proxy statement.

A:    If you are a U.S. Holder (as defined under the caption “The Merger — U.S. Federal Income Tax Consequences of the Merger”), the exchange of Bottomline common stock for cash pursuant to the Merger generally will require you to recognize gain or loss for U.S. federal income tax purposes in an amount equal to the difference, if any, between the amount of cash you received pursuant to the Merger and your adjusted tax basis in the shares of common stock surrendered pursuant to the Merger. A Non-U.S. Holder (as defined under the caption “The Merger — U.S. Federal Income Tax Consequences of the Merger”) generally will not be subject to U.S. federal income tax with respect to the exchange of Bottomline common stock for cash in the Merger unless such Non-U.S. Holder has certain connections to the United States.

You should consult your own tax advisor to determine the U.S. federal income tax consequences of the Merger to you in light of your own particular circumstances and any consequences arising under the laws of any state, local or foreign taxing jurisdiction. A more complete description of certain U.S. federal income tax consequences of the Merger is provided under the caption “The Merger — U.S. Federal Income Tax Consequences of the Merger.”

A:    At the Effective Time, each outstanding stock option, restricted stock award and restricted stock unit award will be credited with the Additional Vesting Credit. For any award of restricted shares or restricted stock units that are subject to performance-based vesting conditions, the number of shares subject to such award will be deemed to have been achieved at the “target” level of performance for such award at the Effective Time.

After giving effect to the Additional Vesting Credit, each outstanding option that is vested will be cancelled and converted into the right to receive an amount in cash (subject to any applicable tax withholding) equal to the product of (1) the amount, if any, by which $57.00 exceeds the exercise price per share of Bottomline common stock underlying such stock option; and (2) the total number of shares of Bottomline common stock subject to such option. It is anticipated that all outstanding stock options will be fully vested and “in-the-money” at the Effective Time.

At the Effective Time, each restricted stock award that is then vested (after giving effect to the Additional Vesting Credit) will be converted into the right to receive the product of (1) $57.00 and (2) the number of shares of Bottomline common stock subject to such restricted stock award, payable promptly following the Effective Time. Each restricted stock award which is unvested as of the Effective Time (after giving effect to the Additional Vesting Credit) will be cancelled at the Effective Time and converted into the right to receive an amount in cash equal to the product of (1) $57.00 and (2) the number of shares of Bottomline common stock subject to such unvested restricted stock award, which amount will, generally subject to the holder’s continued service with the Company, Parent or an affiliate through the applicable vesting date and vest and be payable at the same time and on the same terms as the unvested restricted stock award to which such cash amount relates would have vested pursuant to its terms (except that any applicable performance conditions will be deemed to have been achieved at target levels and after giving effect to Additional Vesting Credit). Additionally, under Bottomline’s 2019 Stock Incentive Plan, if the holder’s employment is terminated other than for cause or by the holder for good reason within two years of the Effective Time, the cash amount to which such restricted stock award relates will immediately vest.

At the Effective Time, each outstanding restricted stock unit award that is then vested (after giving effect to the Additional Vesting Credit) will be converted into the right to receive a payment equal to the product of (1) $57.00 and (2) the number of shares of Bottomline common stock subject to such restricted stock unit award, payable promptly following the Effective Time. Each restricted stock unit award that is unvested as of the Effective Time (after giving effect to the Additional Vesting Credit) will be cancelled at the Effective Time and

converted into the right to receive an amount in cash equal to the product of (1) $57.00 and (2) the number of shares of Bottomline common stock subject to such unvested restricted stock award, which amount will, generally subject to the holder’s continued service with the Company, Parent or an affiliate through the applicable vesting date and vest and be payable at the same time and on the same terms as the unvested restricted stock unit award to which such cash amount relates would have vested pursuant to its terms (except that any applicable performance conditions will be deemed to have been achieved at target levels and after giving effect to Additional Vesting Credit). Additionally, under Bottomline’s 2019 Stock Incentive Plan, if the holder’s employment is terminated other than for cause or by the holder for good reason within two years of the Effective Time, the cash amount to which such restricted stock unit award relates will immediately vest.

A:    The current purchase period under the ESPP will be the final purchase period under the ESPP; to the extent necessary, the current purchase period will be shortened so that the share purchase pursuant to that purchase period will occur prior to the Merger. Any funds remaining in a participant’s account following this final purchase will be refunded to the participant. Shares purchased via the ESPP will be treated in the same manner as other outstanding Bottomline shares in the Merger. There will be no increase in the amount of participants’ payroll deduction elections under the ESPP during the current purchase period and no new participants will be allowed to enroll in the ESPP.

A:    We are working toward completing the Merger as quickly as possible and currently expect to complete the Merger in the second calendar quarter of 2022. However, the exact timing of completion of the Merger cannot be predicted because the Merger is subject to the closing conditions specified in the Merger Agreement, many of which are outside of our control.

A:    If the Merger is completed, Bottomline stockholders who do not vote in favor of the adoption of the Merger Agreement and who properly demand appraisal of their shares will be entitled to appraisal rights in connection with the Merger under Section 262. This means that stockholders are entitled to have their shares appraised by the Delaware Court of Chancery and to receive payment in cash of the “fair value” of their shares of common stock, exclusive of any elements of value arising from the accomplishment or expectation of the Merger, together with interest to be paid on the amount determined to be fair value, if any, as determined by the court, so long as they comply with the procedures established by Section 262. Due to the complexity of the appraisal process, Bottomline stockholders who wish to seek appraisal of their shares are encouraged to seek the advice of legal counsel with respect to the exercise of appraisal rights. The DGCL requirements for exercising appraisal rights are described in additional detail in this proxy statement, and Section 262 regarding appraisal rights is reproduced in Annex C to this proxy statement.

A:    Yes. In considering the recommendation of the Board of Directors with respect to the proposal to adopt the Merger Agreement, you should be aware that our directors and executive officers may have interests in the Merger that are different from, or in addition to, the interests of Bottomline stockholders generally. In (i) evaluating and negotiating the Merger Agreement; (ii) approving the Merger Agreement and the Merger; and (iii) recommending that the Merger Agreement be adopted by Bottomline’s stockholders, the Board of Directors was aware of and considered these interests to the extent that they existed at the time, among other matters. For more information, see the section of this proxy statement captioned “The Merger — Interests of Bottomline’s Directors and Executive Officers in the Merger,” beginning on page 55 of this proxy statement.

A:    If you have any questions concerning the Merger, the Special Meeting or this proxy statement, would like additional copies of this proxy statement or need help voting your shares of Bottomline common stock, please contact our Proxy Solicitor:

Innisfree M&A Incorporated

Stockholders May Call Toll-Free: (877) 687-1865

Banks & Brokers May Call Collect: (212) 750-5833

FORWARD-LOOKING STATEMENTS

This proxy statement and any document referred to in this proxy statement contains “forward-looking statements” within the meaning of the federal securities laws, including Section 27A of the Securities Act of 1933, as amended, and Section 21E of the Securities Exchange Act of 1934, as amended. These forward-looking statements are based on Bottomline’s current expectations, estimates and projections about the expected date of closing of the proposed transaction and the potential benefits thereof, its business and industry, management’s beliefs and certain assumptions made by Bottomline and Thoma Bravo, all of which are subject to change. In this context, forward-looking statements often address expected future business and financial performance and financial condition, and often contain words such as “expect,” “anticipate,” “intend,” “plan,” “believe,” “could,” “seek,” “see,” “will,” “may,” “would,” “might,” “potentially,” “estimate,” “continue,” “expect,” “target,” similar expressions or the negatives of these words or other comparable terminology that convey uncertainty of future events or outcomes. All forward-looking statements by their nature address matters that involve risks and uncertainties, many of which are beyond our control, and are not guarantees of future results, such as statements about the consummation of the proposed transaction and the anticipated benefits thereof. These and other forward-looking statements, including the failure to consummate the proposed transaction or to make or take any filing or other action required to consummate the transaction on a timely matter or at all, are not guarantees of future results and are subject to risks, uncertainties and assumptions that could cause actual results to differ materially from those expressed in any forward-looking statements. Accordingly, there are or will be important factors that could cause actual results to differ materially from those indicated in such statements and, therefore, you should not place undue reliance on any such statements and caution must be exercised in relying on forward-looking statements. Important risk factors that may cause such a difference include, but are not limited to: (i) the completion of the proposed transaction on anticipated terms and timing, including obtaining stockholder and regulatory approvals, anticipated tax treatment, unforeseen liabilities, future capital expenditures, revenues, expenses, earnings, synergies, economic performance, indebtedness, financial condition, losses, future prospects, business and management strategies for the management, expansion and growth of Bottomline’s business and other conditions to the completion of the transaction; (ii) the impact of the COVID-19 pandemic on Bottomline’s business and general economic conditions; (iii) Bottomline’s ability to implement its business strategy; (iv) significant transaction costs associated with the proposed transaction; (v) potential litigation relating to the proposed transaction; (vi) the risk that disruptions from the proposed transaction will harm Bottomline’s business, including current plans and operations; (vii) the ability of Bottomline to retain and hire key personnel; (viii) potential adverse reactions or changes to business relationships resulting from the announcement or completion of the proposed transaction; (ix) legislative, regulatory and economic developments affecting Bottomline’s business; (x) general economic and market developments and conditions; (xi) the evolving legal, regulatory and tax regimes under which Bottomline operates; (xii) potential business uncertainty, including changes to existing business relationships, during the pendency of the merger that could affect Bottomline’s financial performance; (xiii) restrictions during the pendency of the proposed transaction that may impact Bottomline’s ability to pursue certain business opportunities or strategic transactions; and (xiv) unpredictability and severity of catastrophic events, including, but not limited to, acts of terrorism or outbreak of war or hostilities, as well as Bottomline’s response to any of the aforementioned factors. These risks, as well as other risks associated with the proposed transaction, are more fully discussed in this proxy statement. While the list of factors presented here, and the list of factors presented in this proxy statement are considered representative, no such list should be considered to be a complete statement of all potential risks and uncertainties. Unlisted factors may present significant additional obstacles to the realization of forward looking statements. Consequences of material differences in results as compared with those anticipated in the forward-looking statements could include, among other things, business disruption, operational problems, financial loss, legal liability to third parties and similar risks, any of which could have a material adverse effect on Bottomline’s financial condition, results of operations, or liquidity. Bottomline does not assume any obligation to publicly provide revisions or updates to any forward-looking statements, whether as a result of new information, future developments or otherwise, should circumstances change, except as otherwise required by securities and other applicable laws.

THE SPECIAL MEETING

The enclosed proxy is solicited on behalf of the Board of Directors for use at the Special Meeting.

Date, Time and Place

We will hold the Special Meeting on [●],March 8, 2022, at [●], at [●]4 p.m., Eastern time,Time, at [●].325 Corporate Drive, Portsmouth, NH 03801.

Purpose of the Special Meeting

At the Special Meeting, we will ask stockholders to vote on proposals to (i) adopt the Merger Agreement, (ii) adjourn the Special Meeting, if necessary or appropriate, to solicit additional proxies if there are insufficient votes to adopt the Merger Agreement at the time of the Special Meeting and (iii) approve, by non-binding, advisory vote, compensation that will or may become payable by Bottomline to its named executive officers in connection with the Merger.

Record Date; Shares Entitled to Vote; Quorum

Only stockholders of record as of the Record Date are entitled to notice of the Special Meeting and to vote at the Special Meeting. A list of stockholders entitled to vote at the Special Meeting will be available at our principal executive offices, located at 325 Corporate Drive, Portsmouth, New Hampshire 03801 during regular business hours for a period of no less than ten days before the Special Meeting and at the place of the Special Meeting during the meeting.

As of the Record Date, there were [●]44,977,553 shares of common stock outstanding and entitled to vote at the Special Meeting.

The holders of a majority in voting power of the stock issued and outstanding and entitled to vote thereat, present in person or represented by proxy, will constitute a quorum at the Special Meeting. In the event that a quorum is not present at the Special Meeting, it is expected that the meeting will be adjourned to solicit additional proxies.

Vote Required; Abstentions and Broker Non-Votes

The affirmative vote of the holders of a majority of the outstanding shares of Bottomline common stock is required to adopt the Merger Agreement. Adoption of the Merger Agreement by Bottomline’s stockholders is a condition to the closing of the transactions contemplated by the Merger Agreement.

Approval of the proposal to adjourn the Special Meeting requires the affirmative vote of a majority of the shares of stock having voting power present in person or represented by proxy at the Special Meeting and entitled to vote on the subject matter. Approval, by non-binding, advisory vote, of compensation that will or may become payable by Bottomline to its named executive officers in connection with the Merger requires the affirmative vote of a majority of the shares of stock having voting power present in person or represented by proxy at the Special Meeting and entitled to vote on the subject matter.

If a stockholder abstains from voting, that abstention will have the same effect as if the stockholder voted “AGAINST” the proposal to adopt the Merger Agreement. For stockholders who attend the meeting or are represented by proxy and abstain from voting, the abstention will have the same effect as if the stockholder voted “AGAINST” any proposal to adjourn the Special Meeting to a later date to solicit additional proxies if there are insufficient votes to adopt the Merger Agreement at the time of the Special Meeting and “AGAINST” the proposal to approve, by non-binding, advisory vote, compensation that will or may become payable by Bottomline to its named executive officers in connection with the Merger.

Bottomline does not expect any broker non-votes at the Special Meeting because the rules applicable to banks, brokers and other nominees only provide brokers with discretionary authority to vote on proposals that are considered routine, whereas each of the proposals to be presented at the Special Meeting is considered non-routine. As a result, no broker will be permitted to vote your shares of Bottomline common stock at the Special Meeting without receiving instructions. Failure to instruct your broker on how to vote your shares will have the same effect as a vote “AGAINST” the proposal to adopt the Merger Agreement.

Shares Held by Bottomline’s Directors and Executive Officers; Voting Agreement

As of the Record Date,January 24, 2022, our directors and executive officers beneficially owned and were entitled to vote, in the aggregate, [●]2,102,381 shares of common stock, representing approximately [●]%4.7% of the shares of common stock outstanding on the Record Date.January 24, 2022.

We currently expect that our directors and executive officers will vote all of their respective shares of Bottomline common stock: (1) “FOR” the adoption of the Merger Agreement; (2) “FOR” the adjournment of the Special Meeting, if necessary or appropriate, to solicit additional proxies if there are insufficient votes to adopt the Merger Agreement at the time of the Special Meeting; and (3) “FOR” the non-binding, advisory proposal to approve compensation that will or may become payable by Bottomline to its named executive officers in connection with the Merger.

Parent and Bottomline have entered into the Voting Agreement with the Supporting Shareholders, which collectively hold approximately 4% of the outstanding shares of our common stock.stock, as of the date of the Voting Agreement. A copy of the Voting Agreement is attached as Annex D and is incorporated herein by reference. Under the Voting Agreement, the Supporting Shareholders agree, among other things, during the term of the Voting Agreement, to vote their shares of common stock (i) in favor of the adoption of the Merger Agreement and the approval of the transactions contemplated thereby and (ii) against any alternative acquisition proposal, and not to, directly or indirectly, sell, transfer, exchange or otherwise dispose of their shares, subject to certain limited exceptions.

Voting of Proxies

If your shares are registered in your name with our transfer agent, Computershare Trust Company, N.A., you may cause your shares to be voted by returning a signed and dated proxy card in the accompanying prepaid envelope, or you may vote in person at the Special Meeting. Additionally, you may grant a proxy electronically over the Internet or by telephone by following the instructions on your proxy card. You must have the enclosed proxy card available, and follow the instructions on the proxy card, in order to grant a proxy electronically over the Internet or by telephone. Based on your proxy cards or Internet and telephone proxies, the proxy holders will vote your shares according to your directions.

If you plan to attend the Special Meeting and wish to vote in person, you will be given a ballot at the Special Meeting. If your shares are registered in your name, you are encouraged to vote by proxy even if you plan to attend the Special Meeting in person. If you attend the Special Meeting and vote in person by ballot, your vote will revoke any previously submitted proxy.

Voting instructions are included on your proxy card. All shares represented by properly signed and dated proxies received in time for the Special Meeting will be voted at the Special Meeting in accordance with the instructions of the stockholder. Properly signed and dated proxies that do not contain voting instructions will be voted (1) “FOR” adoption of the Merger Agreement; (2) “FOR” the adjournment of the Special Meeting, if necessary or appropriate, to solicit additional proxies if there are insufficient votes to adopt the Merger Agreement at the time of the Special Meeting; and (3) “FOR” the proposal to approve, by non-binding, advisory vote, compensation that will or may become payable by Bottomline to its named executive officers in connection with the Merger.

If your shares are held in “street name” through a bank, broker or other nominee, you may vote through your bank, broker or other nominee by completing and returning the voting form provided by your bank, broker or

other nominee or attending the Special Meeting and voting in person with a “legal proxy” from your bank, broker or other nominee. If such a service is provided, you may vote over the Internet or telephone through your bank, broker or other nominee by following the instructions on the voting form provided by your bank, broker or other nominee. If you do not return your bank’s, broker’s or other nominee’s voting form, do not vote via the Internet or telephone through your bank, broker or other nominee, if possible, or do not attend the Special Meeting and vote in person with a “legal proxy” from your bank, broker or other nominee, it will have the same effect as if you voted “AGAINST” the proposal to adopt the Merger Agreement but will not have any effect on the adjournment proposal or the proposal to approve, by non-binding, advisory vote, compensation that will or may become payable by Bottomline to its named executive officers in connection with the Merger.

Revocability of Proxies

If you are a stockholder of record, you may change your vote or revoke your proxy at any time before it is voted at the Special Meeting by:

If you have submitted a proxy, your appearance at the Special Meeting, in the absence of voting in person or submitting an additional proxy or revocation, will not have the effect of revoking your prior proxy.

If you hold your shares of common stock in “street name,” you should contact your bank, broker or other nominee for instructions regarding how to change your vote. You may also vote in person at the Special Meeting if you obtain a “legal proxy” from your bank, broker or other nominee.

Any adjournment, postponement or other delay of the Special Meeting, including for the purpose of soliciting additional proxies, will allow stockholders who have already sent in their proxies to revoke them at any time prior to their use at the Special Meeting as adjourned, postponed or delayed.

Board of Directors’ Recommendation

The Board of Directors, after considering various factors described under the caption “The Merger — Recommendation of the Board of Directors and Reasons for the Merger,” has unanimously (1) adopted and declared advisable the merger agreement and the transactions contemplated by the Merger Agreement; (2) declared that it is in the best interests of Bottomline and its stockholders that Bottomline enter into the merger agreement and consummate the transactions contemplated by the merger agreement, in each case on the terms and subject to the conditions set forth in the merger agreement; and (3) declared that the terms of the merger agreement are fair to Bottomline and its stockholders. The Board of Directors unanimously recommends that you vote (1) “FOR” the adoption of the Merger Agreement; (2) “FOR” the adjournment of the Special Meeting, if necessary or appropriate, to solicit additional proxies if there are insufficient votes to adopt the Merger Agreement at the time of the Special Meeting; and (3) “FOR” the proposal to approve, by non-binding, advisory vote, compensation that will or may become payable by Bottomline to its named executive officers in connection with the Merger.

Solicitation of Proxies

The expense of soliciting proxies will be borne by Bottomline. We have retained Innisfree M&A Incorporated, a proxy solicitation firm (the “Proxy Solicitor”), to solicit proxies in connection with the Special Meeting at a cost

of approximately $75,000, plus a success fee of $75,000, and expenses. We will also indemnify the Proxy Solicitor against losses arising out of its provisions of these services on our behalf. In addition, we may reimburse banks, brokers and other nominees representing beneficial owners of shares for their expenses in forwarding soliciting materials to such beneficial owners. Proxies may also be solicited by our directors, officers and employees, personally or by telephone, email, fax, over the Internet or other means of communication. No additional compensation will be paid for such services.

Anticipated Date of Completion of the Merger

Assuming timely satisfaction of necessary closing conditions, including the approval by Bottomline’s stockholders of the proposal to adopt the Merger Agreement, we anticipate that the Merger will be consummated in the second calendar quarter of 2022.

Appraisal Rights

If the Merger is completed, stockholders who do not vote in favor of the adoption of the Merger Agreement and who properly demand appraisal of their shares will be entitled to appraisal rights in connection with the Merger under Section 262. This means that stockholders are entitled to have their shares appraised by the Delaware Court of Chancery and to receive in lieu of the Per Share Merger Consideration payment in cash of the amount determined by the Delaware Court of Chancery to be the “fair value” of their shares of common stock, exclusive of any elements of value arising from the accomplishment or expectation of the Merger, together with interest to be paid on the amount determined to be fair value, if any, as determined by the court, so long as they comply with the procedures established by Section 262. Due to the complexity of the appraisal process, stockholders who wish to seek appraisal of their shares are encouraged to seek the advice of legal counsel with respect to the exercise of appraisal rights.

Stockholders considering seeking appraisal should be aware that the fair value of their shares as determined pursuant to Section 262 could be more than, the same as or less than the value of the Per Share Merger Consideration.

Stockholders wishing to exercise the right to seek an appraisal of their shares of common stock must do ALL of the following:

Your failure to follow exactly the procedures specified under the DGCL will result in the loss of your appraisal rights. The DGCL requirements for exercising appraisal rights are described in further detail in the section captioned “The Merger — Appraisal Rights,” of this proxy statement, and Section 262, the relevant section of the DGCL regarding appraisal rights, is reproduced and attached as Annex C to this proxy statement. If you hold your shares of common stock through a bank, broker or other nominee and you wish to exercise appraisal rights, you should consult with your bank, broker or other nominee to determine the appropriate procedures for the making of a demand for appraisal by such bank, broker or nominee.

Other Matters

At this time, we know of no other matters to be voted on at the Special Meeting. If any other matters properly come before the Special Meeting, your shares of common stock will be voted in accordance with the discretion of the appointed proxy holders.

Important Notice Regarding the Availability of Proxy Materials for the Stockholder Meeting to be Held on [●],March 8, 2022

The proxy statement is available at www.investors.bottomline.com.

Householding of Special Meeting Materials

Unless we have received contrary instructions, we may send a single copy of this proxy statement to any household at which two or more stockholders reside if we believe the stockholders are members of the same family. Each stockholder in the household will continue to receive a separate proxy card. This process, known as “householding,” reduces the volume of duplicate information received at your household and helps to reduce our expenses.

If you would like to receive your own set of our disclosure documents, follow the instructions described below. Similarly, if you share an address with another stockholder and together both of you would like to receive only a single set of our disclosure documents, follow these instructions.

We will promptly deliver, upon oral or written request, a separate copy of the proxy materials to any stockholder residing at an address to which only one copy was mailed, if you contact us by writing to Bottomline Technologies, Inc., Attention: Investor Relations, 325 Corporate Drive, Portsmouth, New Hampshire 03801 or call our Investor Relations Department at (603) 501-4840. Eligible stockholders of record receiving multiple copies of this proxy statement can request householding by contacting us in the same manner. If a bank, broker or other nominee holds your shares, please contact your bank, broker or other nominee directly.

Questions and Additional Information

If you have any questions concerning the Merger, the Special Meeting or this proxy statement, would like additional copies of this proxy statement or need help voting your shares of common stock, please contact our Proxy Solicitor:

Innisfree M&A Incorporated

Stockholders May Call Toll-Free: (877) 687-1865

Banks & Brokers May Call Collect: (212) 750-5833

PROPOSAL 1: ADOPTION OF THE MERGER AGREEMENT

We are asking you to approve and adopt the Merger Agreement and the Merger contemplated by the Merger Agreement.

For a summary of and detailed information regarding this proposal, see the information about the Merger Agreement and the Merger throughout this proxy statement, including the information set forth in the sections captioned “The Merger” beginning on page 3031 of this proxy statement and “The Merger Agreement” beginning on page 7374 of this proxy statement. A copy of the Merger Agreement is attached to this proxy statement as Annex A. You are urged to read the Merger Agreement carefully in its entirety.

Under applicable law, we cannot complete the Merger without the affirmative vote of a majority of the outstanding shares of Bottomline common stock voting in favor of the proposal to approve and adopt the Merger Agreement and the Merger. If you abstain from voting, fail to cast your vote, in person or by proxy, or fail to give voting instructions to your brokerage firm, bank, trust or other nominee, it will have the same effect as a vote against the proposal to adopt the Merger Agreement.

The Board of Directors unanimously recommends that you vote “FOR” this proposal.

PROPOSAL 2: ADJOURNMENT OF THE SPECIAL MEETING

We are asking you to approve a proposal to adjourn the Special Meeting to a later date or dates if necessary or appropriate to solicit additional proxies if there are insufficient votes to adopt the Merger Agreement at the time of the Special Meeting. If stockholders approve the adjournment proposal, we could adjourn the Special Meeting and any adjourned session of the Special Meeting and use the additional time to solicit additional proxies, including proxies from stockholders that have previously returned properly executed proxies voting against adoption of the Merger Agreement. Among other things, approval of the adjournment proposal could mean that, even if we had received proxies representing a sufficient number of votes against adoption of the Merger Agreement such that the proposal to adopt the Merger Agreement would be defeated, we could adjourn the Special Meeting without a vote on the adoption of the Merger Agreement and seek to convince the holders of those shares to change their votes to votes in favor of adoption of the Merger Agreement. Additionally, we may seek to adjourn the Special Meeting if a quorum is not present or otherwise at the discretion of the chairman of the Special Meeting.

The Board of Directors unanimously recommends that you vote “FOR” this proposal.

PROPOSAL 3: ADVISORY, NON-BINDING VOTE ON MERGER-RELATED

EXECUTIVE COMPENSATION ARRANGEMENTS

Section 14A of the Exchange Act, which was enacted as part of the Dodd-Frank Wall Street Reform and Consumer Protection Act of 2010, requires that we provide stockholders with the opportunity to vote to approve, on an advisory, non-binding basis, the payment of certain compensation that will or may become payable by Bottomline to its named executive officers in connection with the Merger, as disclosed in the section captioned “The Merger — Interests of Bottomline’s Directors and Executive Officers in the Merger,” beginning on page 55 of this proxy statement.

We are asking stockholders to indicate their approval of the various items of compensation that will or may become payable by Bottomline to its named executive officers in connection with the Merger. These payments are set forth in the section captioned “The Merger — Interests of Bottomline’s Directors and Executive Officers in the Merger— Golden Parachute Compensation,” beginning on page 60 of this proxy statement, and the accompanying footnotes. In general, the various plans and arrangements pursuant to which these compensation payments may be made have previously formed part of Bottomline’s overall compensation program for our named executive officers.

Accordingly, we are seeking approval of the following resolution at the Special Meeting:

“RESOLVED, that the stockholders of Bottomline Technologies, Inc. approve, on a nonbinding, advisory basis, the compensation that will or may become payable by Bottomline to its named executive officers that is based on or otherwise relates to the Merger as disclosed pursuant to Item 402(t) of Regulation S-K in the section captioned “The Merger — Interests of Bottomline’s Directors and Executive Officers in the Merger— Golden Parachute Compensation.”

Stockholders should note that the approval of this proposal is not a condition to completion of the Merger, and as an advisory vote, the result will not be binding on Bottomline, the Board of Directors, Parent or the named executive officers. Further, certain payments under the underlying plans and arrangements are contractual in nature and not, by their terms, subject to stockholder approval. Accordingly, regardless of the outcome of the advisory vote, if the Merger is consummated our named executive officers will be eligible to receive the compensation that is based on or otherwise relates to the Merger in accordance with the terms and conditions of the underlying plans and agreements and the Merger Agreement.

The Board of Directors unanimously recommends that you vote “FOR” this proposal.

THE MERGER

This discussion of the Merger is qualified in its entirety by reference to the Merger Agreement, which is attached to this proxy statement as Annex A and incorporated into this proxy statement by reference. You should read the entire Merger Agreement carefully as it is the legal document that governs the Merger.

Parties Involved in the Merger

Bottomline Technologies, Inc.

325 Corporate Drive

Portsmouth, New Hampshire 03801

(603) 436-0700

Bottomline makes complex business payments simple, smart and secure. Corporations and banks rely on Bottomline for domestic and international payments, efficient cash management, automated workflows for payment processing and bill review, and fraud detection, behavioral analytics and regulatory compliance solutions. Thousands of corporations around the world benefit from Bottomline solutions. Headquartered in Portsmouth, NH, Bottomline delights customers through offices across the U.S., Europe and Asia-Pacific.

Bottomline’s common stock is listed on NASDAQ under the symbol “EPAY”.

Bottomline Intermediate Holdings III, LLC (formerly known as Project RB Parent, LLC)

c/o Thoma Bravo, L.P.

600 Montgomery Street, 20th Floor

San Francisco, California 91444

(415) 263-3660

Parent was formed on December 9, 2021, solely for the purpose of engaging in the transactions contemplated by the Merger Agreement and has not engaged in any business activities other than in connection with the transactions contemplated by the Merger Agreement and arranging of the equity financing in connection with the Merger.

Project RB Merger Sub, Inc.

c/o Thoma Bravo, L.P.

600 Montgomery Street, 20th Floor

San Francisco, California 9144

(415) 263-3660

Merger Sub is a wholly owned indirect subsidiary of Parent and was formed on December 9, 2021, solely for the purpose of engaging in the transactions contemplated by the Merger Agreement and has not engaged in any business activities other than in connection with the transactions contemplated by the Merger Agreement and arranging of the equity financing in connection with the Merger.

Parent and Merger Sub are each affiliated with the Thoma Bravo Fund. In connection with the transactions contemplated by the Merger Agreement, (1) the Thoma Bravo Fund has provided to Parent an equity commitment of an amount equal to the estimated amount of aggregate consideration that will be due and payable at closing, the aggregate proceeds of which will be sufficient for Parent and Merger Sub to pay the aggregate merger consideration at the closing of the transactions contemplated by the Merger Agreement and all related fees and expenses (pursuant to the terms and conditions as described further under the caption “The Merger — Financing of the Merger,” beginning on page 63 of this proxy statement). After giving effect to the Merger, Bottomline, as the Surviving Corporation, will be affiliated with the Thoma Bravo Fund.

Effect of the Merger

Upon the terms and subject to the conditions of the Merger Agreement, if the Merger is completed, Merger Sub will merge with and into Bottomline, and Bottomline will continue as the Surviving Corporation and as a wholly owned subsidiary of Parent. As a result of the Merger, our common stock will no longer be publicly traded and will be delisted from NASDAQ. In addition, our common stock will be deregistered under the Exchange Act, and we will no longer file periodic reports with the SEC. If the Merger is completed, you will not own any shares of the capital stock of the Surviving Corporation.

The Effective Time will occur upon the filing of a certificate of merger with the Secretary of State of the State of Delaware (or at such later time as we, Parent and Merger Sub may agree and specify in the certificate of merger).

Effect on Bottomline if the Merger is Not Completed

If the Merger Agreement is not adopted by Bottomline’s stockholders or if the Merger is not completed for any other reason, stockholders will not receive any payment for their shares of common stock. Instead, Bottomline will remain an independent public company, our common stock will continue to be listed and traded on NASDAQ and registered under the Exchange Act and we will continue to file periodic reports with the SEC. In addition, if the Merger is not completed, we expect that stockholders will continue to be subject to the same risks and opportunities to which they are currently subject, including risks related to the highly competitive industry in which Bottomline operates and risks related to adverse economic conditions.

Furthermore, if the Merger is not completed, and depending on the circumstances that caused the Merger not to be completed, the price of our common stock may decline significantly. If that were to occur, it is uncertain when, if ever, the price of our common stock would return to the price at which it trades as of the date of this proxy statement.

Accordingly, if the Merger is not completed, there can be no assurance as to the effect of these risks and opportunities on the future value of your shares of common stock. If the Merger is not completed, the Board of Directors will continue to evaluate and review Bottomline’s business operations, strategic direction and capitalization, among other things, and will make such changes as are deemed appropriate. If the Merger Agreement is not adopted by Bottomline’s stockholders or if the Merger is not completed for any other reason, there can be no assurance that any other transaction acceptable to the Board of Directors will be offered or that Bottomline’s business, prospects or results of operation will not be adversely impacted.

Upon termination of the Merger Agreement under specified circumstances, Bottomline will be required to pay Parent a termination fee of $78,000,000. In addition, in certain circumstances, Bottomline will be required to reimburse Parent for up to $5,000,000 of its expenses associated with the transactions contemplated by the Merger Agreement (with such reimbursement deducted from the termination fee, should it not be payable at the time of such termination but subsequently become payable). For more information please see the section captioned “The Merger Agreement — Termination Fees and Expense Reimbursement,” beginning on page 9798 of this proxy statement.

Merger Consideration

In the Merger, each outstanding share of common stock (other than shares owned by (1) Parent or Merger Sub and (2) stockholders who are entitled to and who properly exercise appraisal rights under the DGCL) will be converted into the right to receive the Per Share Merger Consideration.

After the Merger is completed, you will have the right to receive the Per Share Merger Consideration, but you will no longer have any rights as a stockholder (except that stockholders who properly exercise their appraisal rights will have the right to receive a payment for the “fair value” of their shares as determined pursuant to an appraisal proceeding as contemplated by the DGCL, as described below under the caption “—Appraisal Rights,” beginning on page 64 of this proxy statement.)

Background of the Merger

The following chronology summarizes the key meetings and events that led to the signing of the Merger Agreement. This chronology does not purport to catalogue every conversation of or among members of the Board of Directors, Thoma Bravo, the Company’s representatives, Thoma Bravo’s representatives, and other parties. Other than as described below, there have been no material contacts between the Company and Thoma Bravo in the past two years.

As part of its ongoing evaluation of Bottomline’s business, the Board of Directors, together with senior management, regularly reviews and assesses Bottomline’s strategic direction, financial performance and business plans with a view towards strengthening Bottomline’s business and identifying opportunities to increase stockholder value. Representatives of private equity firms and potential strategic partners have from time to time contacted and/or met with members of Company management to discuss the Company’s business, with a view to exploring whether to pursue a potential transaction with the Company.

On February 5, 2021, a representative of a private equity firm (“Party D”) contacted Robert Eberle, the Chief Executive Officer of the Company, seeking to receive an update on the Company’s business. This representative subsequently expressed to Mr. Eberle an interest in exploring a potential acquisition of the Company. As further described below, Mr. Eberle and other Company representatives engaged in periodic discussions with Party D during the period leading up to Party D’s submission of a written expression of interest with respect to a transaction involving the Company.

On April 6, 2021, a representative of a private equity firm (“Party E”) contacted Mr. Eberle, seeking to receive an update on the Company’s business. This representative subsequently expressed to Mr. Eberle an interest in exploring a potential acquisition of the Company. As further described below, Mr. Eberle and other Company representatives engaged in periodic discussions with Party E during the period leading up to mid-September 2021, but when Party E learned that the Company would be undertaking a process to solicit interest from potential acquirors, Party E indicated it did not intend to participate in the process.

On April 13, 2021, a representative of a private equity firm (“Party B”) contacted Mr. Eberle, seeking to receive an update on the Company’s business. This representative subsequently expressed to Mr. Eberle an interest in exploring a potential acquisition of the Company. As further described below, Mr. Eberle and other Company representatives engaged in periodic discussions with Party B during the period leading up to the Company’s entry into an exclusivity agreement with Thoma Bravo on December 9, 2021.

In light of the various expressions of interest described above, Mr. Eberle contacted representatives of Deutsche Bank, whose lead representative had a long-standing relationship with the Company and familiarity with the Company’s business, and requested a meeting, which meeting occurred on April 16, 2021. During this meeting, Mr. Eberle and Bruce Bowden, the Company’s Chief Financial Officer, discussed Deutsche Bank’s perspectives, based on public information, concerning a range of potential strategic alternatives for the Company and market perspectives of the Company.

On April 26, 2021, a representative of a private equity firm (“Party F”) contacted Mr. Eberle, seeking to receive an update on the Company’s business. This representative subsequently expressed to Mr. Eberle an interest in exploring a potential acquisition of the Company. As further described below, Mr. Eberle and other Company representatives engaged in periodic discussions with Party F during the period leading up to early December 2021, including submitting a written expression of interest as described below.

On May 4, 2021, the Company publicly announced earnings for its 2021 third fiscal quarter and provided guidance for the upcoming 2022 fiscal year. The Company’s financial performance had met Wall Street consensus revenue and earnings targets and the Company’s publicly disclosed guidance for the 2021 third fiscal

quarter. However, the Company’s 2022 fiscal year guidance reflected the Company’s expectation of focusing on growth investments and accelerating subscription revenue growth, and as a consequence reflected anticipated earnings that were lower than Wall Street consensus for the 2022 fiscal year. The Company’s stock price traded down by more than 20% within the two trading days after this announcement.

On May 11, 2021, the Board of Directors met to discuss perspectives on the Company’s strategic plan in light of the negative market reaction following the Company’s announcement of its 2021 third fiscal quarter results and 2022 fiscal year guidance. The Board of Directors discussed the potential opportunities and challenges faced by the Company in seeking to execute on its long-term business plans, including that the Company’s ability to invest in growth opportunities was constrained by stockholder focus on near-term profitability, affecting both investment in product development as well as sales and marketing and go-to-market activities for existing products, and that this could create disadvantages over the longer term relative to competitors with public or private market valuations based on growth rather than earnings. The Board of Directors also discussed the Company’s past success in using acquisitions to enhance its product offerings and market scope as new technologies and opportunities emerged, and the fact that it had become more difficult to execute successful acquisitions given the increased valuations of potentially attractive targets and the constraints on the Company’s ability to invest in acquisitions relative to competitors with public or private market valuations based on growth rather than earnings, and that the Board of Directors and the Company’s senior management expected this challenge to persist. In addition, the Board of Directors discussed concerns relative to attracting and retaining key, experienced talent at various levels of the Company’s business, and the fact that these concerns could worsen in the future given both the constraints on the Company’s ability to offer competitive compensation relative to some competitors with public or private market valuations based on growth rather than earnings and the negative impact of the Company’s recent stock price decline on employee incentives. Following discussion of these matters, the Board of Directors discussed a variety of potential strategic alternatives in addition to continuing to seek to execute on the Company’s long-term business plans, including the possibility of a spin-off or divestiture of one or more business units and the possibility of a sale of the Company to either a strategic or a financial buyer.    The Board of Directors discussed the Company’s recent interactions with private equity firms (which interactions had been discussed informally with various members of the Board of Directors prior to May 11, 2021). The Board of Directors discussed the risk that exploring potential strategic and financial buyer interest in a transaction, in particular through a process with broad outreach, could become publicly known and negatively impact new bookings, customer relationships and the Company’s ability to attract and retain key talent. Following discussion, the Board of Directors authorized Mr. Eberle to work with necessary members of Company management and Deutsche Bank to implement a process to confidentially solicit indications of interest, based on publicly available information, from leading private equity firms viewed as best positioned to offer the highest value for the Company, to enable the Board of Directors to consider feedback and further evaluate whether or not to pursue a potential sale or marketing process (as opposed to continuing to execute the Company’s long-term business plans or pursuing other strategic alternatives) and whether or not to contact additional potential financial buyers or strategic buyers. No decision was made to pursue a sale or marketing process at that time.

On May 17, 2021, Mr. Eberle and Mr. Bowden met with representatives of Deutsche Bank and further discussed potential strategic alternatives, including a process for outreach to a select number of private equity firms, consistent with Mr. Eberle’s discussion with the Board of Directors on May 11, 2021, to explore a sale of the Company and the possibility of outreach to additional parties depending on initial feedback.

On June 7, 2021, Brian Jaffee of Thoma Bravo contacted Mr. Eberle seeking to receive an update on the Company’s business. Mr. Jaffee subsequently expressed to Mr. Eberle an interest in exploring a potential acquisition of the Company, but no specific acquisition proposal was discussed.

On June 9, 2021, a representative of a private equity firm (“Party C”) contacted Mr. Eberle, seeking to receive an update on the Company’s business. This representative subsequently expressed to Mr. Eberle an interest in

exploring a potential acquisition of the Company. As further described below, Mr. Eberle and other Company representatives engaged in periodic discussions with Party C during the period leading up to early December 2021.

On June 17, 2021, Mr. Bowden met with a representative of a private equity firm (“Party G”) at the representative’s request at an investor conference. Thereafter, on July 6, 2021, a representative of Party G contacted Mr. Eberle, seeking to better understand the Company’s business.

On July 16, 2021, a representative of a private equity firm (“Party H”) contacted Mr. Eberle, seeking to receive an update on the Company’s business. This representative subsequently expressed to Mr. Eberle an interest in exploring a potential acquisition of the Company. As further described below, Mr. Eberle and other Company representatives engaged in periodic discussions with Party H during the period leading up to mid-October 2021.

On August 25, 2021, Mr. Eberle and Mr. Bowden had a meeting with representatives of Party G who expressed an interest in exploring a potential acquisition of the Company. As further described below, Mr. Eberle and other Company and Deutsche Bank representatives engaged in periodic discussions with Party G during the period leading up to early December 2021.

On September 1, 2021, Mr. Eberle had a meeting with the CEO of a potential strategic partner (“Party A”). This meeting was scheduled at the request of Party A’s CEO. At the meeting, Party A’s CEO expressed to Mr. Eberle an interest in exploring a potential strategic combination with the Company. Later that day, the Board of Directors held a meeting, attended by members of the Company’s senior management and representatives of the Company’s outside corporate counsel at Wilmer Cutler Pickering Hale and Dorr LLP (“WilmerHale”), for the purpose of updating the Board of Directors on Mr. Eberle’s meeting with the CEO of Party A. Mr. Eberle reported that the CEO of Party A had expressed interest in exploring the possibility of a strategic transaction between the Company and Party A, but had not made a specific proposal or provided any indication of the terms of such a transaction.

On September 9, 2021, the CEO of Party A contacted Mr. Eberle, inquiring again whether the Company would be interested in discussing a potential strategic transaction with Party A. The CEO of Party A indicated to Mr. Eberle that the CEO had not discussed a potential transaction with his board, or received authority from his board to make an offer, and that Party A had not engaged a financial advisor for such a transaction, but that the CEO believed such a transaction could be priced at $52.00 per share and could consist of a combination of cash and stock consideration with a significant component of stock. The CEO of Party A noted that he was not yet prepared to identify the source of any financing for the cash component of the consideration and would require approximately two months before he would be able to do so.

On September 10, 2021, Mr. Jaffee from Thoma Bravo and Mr. Eberle had a telephone conversation regarding Mr. Jaffee’s interest in receiving an update on the Company’s business. No specific acquisition proposal was discussed at the time.

On September 10, 2021, the Board of Directors held a meeting, attended by members of the Company’s senior management, representatives of WilmerHale and representatives of Skadden, Arps, Slate, Meagher & Flom LLP, the Company’s outside counsel for strategic matters (“Skadden”). Mr. Eberle reported to the Board of Directors regarding outreach he had received the prior day from the CEO of Party A, including the lack of board or financial advisor involvement by Party A at this stage, the proposed valuation, and the mix of consideration. Mr. Eberle also noted that the Company had received outreach from several potential private equity acquirors looking to engage in discussions with the Company. After discussion, the Board of Directors determined that it would not be in the Company’s best interest at this time to engage in further discussion with Party A given the speculative nature of Party A’s outreach and concerns raised by the Board of Directors, including with respect to the ability of Company A to finance the cash consideration and the prospects of Company A, but acknowledged that it may be appropriate at a later date to discuss a more concrete proposal. Accordingly, the Board of Directors agreed that Mr. Eberle would communicate that message to the CEO of Party A.

Mr. Eberle then updated the Board of Directors on outreach he had received on September 8, 2021, from representatives of Sachem Head Capital Management LP (“Sachem Head”), which indicated that it was working with Clearfield Capital Management LP (“Clearfield”) and that together, they held approximately 4% of the Company’s outstanding shares beneficially, and 8% economically. The Board of Directors discussed this outreach with representatives of Skadden, and determined that it was advisable for Mr. Eberle to engage in further discussion with Sachem Head and Clearfield.

On September 13, 2021, the Board of Directors held a meeting, attended by members of the Company’s senior management and representatives of Skadden and WilmerHale. Mr. Eberle reported on a call that he and Mr. Bowden had with representatives of Sachem Head and Clearfield that day, during which those representatives requested that the Company agree to accept director nominations from Sachem Head and Clearfield for up to one month after the current director nomination deadline to allow for further discussions with the Company. The representatives of Sachem Head and Clearfield had indicated that they believed the Company was undervalued, explained their views on the factors causing the undervaluation, and suggested that Mr. Hilal, the founder and Chief Investment Officer of Clearfield, chair a newly formed special committee of the Board of Directors to evaluate alternatives for accelerating growth and enhancing stockholder value. The representatives of Sachem Head and Clearfield also indicated their desire to put forward two nominees to the Board of Directors, proposed that the Company declassify the Board of Directors, requested that the nomination deadline be extended to allow for further discussion to achieve a settlement, and indicated that if the deadline were not extended, they were prepared to submit a nomination for two directors and proceed with a proxy contest. The Board of Directors discussed the various potential outcomes of an activist campaign and the risks to the Company of such a process. The Board of Directors recommended that Mr. Eberle continue discussions with Sachem Head and Clearfield to see if a mutually agreeable resolution would be possible. The Board of Directors also discussed the recent inbound interest in a strategic transaction for the Company detailed above, and authorized Company management to engage in discussions with Deutsche Bank with respect to formalizing its relationship with the Company.

Between September 13, 2021 and September 23, 2021, discussions continued between Mr. Eberle (acting in consultation with Joseph Mullen, Chairperson of the Board of Directors) and representatives of Sachem Head and Clearfield, as well as between representatives of Skadden and representatives of Schulte Roth & Zabel LLP (“SRZ”), counsel to Sachem Head and Clearfield.

On September 23, 2021, an executive session of the Board of Directors was held, with members of the Company’s senior management and representatives of Skadden and WilmerHale attending. At the executive session, the Board of Directors discussed whether to engage Deutsche Bank as a financial advisor to the Company in connection with a potential evaluation of strategic alternatives for the Company. The Board of Directors discussed Deutsche Bank’s industry knowledge and expertise, and familiarity with the Company, and the fact that the lead representative of Deutsche Bank had a long-standing working relationship with the Company. After discussion, the Board of Directors authorized the Company to engage Deutsche Bank as financial advisor to the Company. After representatives of Deutsche Bank joined the meeting, representatives of Skadden described the current status of settlement discussions with Sachem Head and Clearfield. After discussion, the Board of Directors authorized Company management to respond to the proposed settlement with Sachem Head and Clearfield.

Later on September 23, 2021, a representative of Deutsche Bank contacted a representative of a potential strategic buyer to assess its interest in exploring a strategic transaction with the Company. This representative did not express interest in further evaluating a potential transaction.

On October 2, 2021, a representative of a private equity firm (“Party I”) contacted Mr. Eberle, seeking to receive an update on the Company’s business. This representative subsequently expressed to Mr. Eberle an interest in exploring a potential acquisition of the Company, but noted that Party I would need to determine its equity commitment sources and that if an auction were to occur, Party I would not likely be the highest bidder. Mr. Eberle and representatives of Deutsche Bank engaged in periodic discussions with Party I during the period leading up to late October 2021.

On October 4, 2021, the Board of Directors held a meeting, attended by members of the Company’s senior management and representatives of Skadden and WilmerHale. The Board of Directors discussed a revised settlement proposal from Sachem Head and Clearfield, and authorized Company management to respond to the revised proposed settlement and agree to, among other things, the appointment of three new directors to the Board of Directors, the formation of a new Strategy Committee of the Board of Directors, a one-year standstill, and declassification of the Board of Directors in 2022.

During early October 2021, a representative of the Company and/or a representative of Deutsche Bank conveyed to Thoma Bravo, Party B, Party C, Party D, Party E, Party G, Party H and Party I that if these parties wished to further pursue a transaction with the Company and obtain access to non-public information, they should submit to Deutsche Bank in the near term a written indication of interest with a proposed valuation for the Company, their proposed due diligence requests and a summary of their proposed material terms for a potential acquisition of the Company. Party F was not contacted at this time as the Company believed that Party F was unlikely to engage at this time due to their lack of engagement and interest in recent months.

On October 12, 2021, the Nominations and Corporate Governance Committee (the “NCGC”) of the Board of Directors held a meeting, attended by members of the Company’s senior management and representatives of Skadden and WilmerHale. Conditioned upon the execution of a settlement agreement with Sachem Head and Clearfield, the NCGC recommended that the Board of Directors appoint three new directors to the Board of Directors, appoint one of the new directors to the NCGC, appoint one of the new directors to the Leadership Development and Compensation Committee of the Board of Directors, and form a Strategy Committee of the Board of Directors consisting of two of the new directors and four other directors.

On October 19, 2021, the Board of Directors held a meeting, attended by members of the Company’s senior management and representatives of Skadden and WilmerHale. The Board of Directors considered and approved the final terms of the proposed settlement with Sachem Head and Clearfield, including the proposed appointment of three new directors to the Board of Directors and the formation of a new Strategy Committee of the Board of Directors.

Also on October 19, 2021, a representative of Party G informed Mr. Eberle that Party G was working on a written indication of interest with support from its investment committee and expressed confidence in Party G’s ability to enter into a definitive agreement for a transaction within three weeks. On October 20, 2021, the Company issued a press release announcing that, following engagement with stockholders Sachem Head and Clearfield, it had agreed to appoint three new directors to the Board of Directors, effective November 8, 2021. In addition, the Company announced that the Board of Directors had formed a new Strategy Committee responsible for evaluating and making recommendations with respect to the Company’s market position and strategy, acceleration of subscription revenue growth and opportunities to create additional stockholder value. The Company’s stock price traded up by more than 15% within the two trading days after this announcement.

Between October 19 and October 26, 2021, three private equity firms (Thoma Bravo, Party B and Party C), submitted initial written indications of interest with proposed price ranges. Thoma Bravo’s indication of interest, received on October 22, 2021, proposed an acquisition of the Company in the range of $52.00 to $55.00 per share. Party B proposed an acquisition of the Company in a range of $50.00 to $55.00 per share, and Party C proposed a range of $50.00 to $52.00 per share. In addition, two other private equity firms (Party D and Party I) submitted written expressions of interest during this period, with no specific proposed valuation. None of these parties were provided non-public information by the Company in order to formulate these indications or expressions of interest.

On October 26, 2021, the Board of Directors held a meeting, with members of the Company’s senior management and representatives of Deutsche Bank, Skadden and WilmerHale in attendance. Mr. Eberle updated the Board of Directors on inbound inquiries that the Company had received expressing interest in exploring a strategic transaction with the Company, including with respect to the five private equity firms (Thoma Bravo,

Party B, Party C, Party D and Party I) that had submitted written indications or expressions of interest. Mr. Eberle noted that four other private equity firms that had initially expressed interest in a transaction with the Company had not submitted written indications of interest (Party E, Party F, Party G and Party H), one strategic party (Party A) that had originally expressed interest had not been invited to submit a written indication of interest, another strategic party that was not Party A had responded to outreach from Deutsche Bank on October 22, 2021, indicating that its interest did not include an acquisition of the entire Company, and a third strategic party had responded to outreach from Deutsche Bank indicating that it was not interested in engaging with the Company due to lack of a strategic fit. The Board of Directors also discussed the Company’s current five-year financial model for the Company and opportunities and challenges facing the Company in the coming years. After discussion, the Board of Directors authorized Company management to enter into non-disclosure agreements (“NDAs”) with four of the five private equity firms (Thoma Bravo, Party B, Party C and Party D) that had submitted written indications or expressions of interest, and to provide non-public information to such firms. The Board of Directors determined that the Company should terminate discussions with the fifth private equity firm (Party I) based on its belief that any potential offer from Party I would require validating sources of funds including third party equity commitments. The Board of Directors authorized Deutsche Bank to make additional outreach to certain specified strategic parties and additional private equity firms, which were selected by Deutsche Bank based on its knowledge of the Company and the markets in which it operates, and seek to determine their level of interest in a potential transaction with the Company. The Board of Directors also determined not to pursue further discussions with the four private equity firms that had not submitted written indications of interest (Party E, Party F, Party G and Party H) and Party A for several reasons, including the valuation proposed, the uncertainty as to the source of the cash component of Party A’s original proposal, and the uncertainty created by the likely need for a vote by Party A’s stockholders.

Following the October 26, 2021 meeting of the Board of Directors, representatives of Deutsche Bank contacted five additional strategic parties and three additional private equity firms consistent with discussion with the Board of Directors.

Between November 8, 2021 and December 4, 2021, the Company executed NDAs with seven private equity firms consistent with discussions with the Board of Directors, including the four private equity firms that had submitted written indications or expressions of interest and were discussed with the Board of Directors on October 26, 2021 (this included Thoma Bravo, which entered into an NDA on November 11, 2021, and Party B, which entered into an NDA on November 8, 2021, Party D, which entered into an NDA on November 10, 2021, and Party F, which entered into an NDA on December 4, 2021). All seven of the NDAs included standstill provisions which would automatically terminate upon announcement by the Company of an acquisition transaction. None of the strategic parties with whom the Company or its representatives had contact (whether before or after the October 26, 2021 meeting of the Board of Directors) entered into an NDA with the Company and, except for the discussions with Party A described above, all of these strategic parties either expressed a lack of interest in pursuing an acquisition of the Company or failed to respond following outreach.

Beginning on November 15, 2021, management conducted management presentations with each of the seven private equity firms that had entered into NDAs with the Company. Six of the seven firms were then given access to a virtual data room that had been established by the Company to facilitate due diligence. The seventh firm declined data room access.

On November 17, 2021, the Board of Directors held a meeting, with members of the Company’s senior management and representatives of Deutsche Bank, Skadden and WilmerHale in attendance. Representatives of Skadden reviewed the role of the Board of Directors in a potential sale transaction and discussed related legal considerations. Company management reviewed with the Board of Directors the Company’s five-year financial model that would be provided to potential acquirors and used for purposes of financial analyses to be conducted by Deutsche Bank, which management noted was a more detailed version of the model discussed at the meeting of the Board of Directors on October 26, 2021. This financial model is identical, other than immaterial differences, to the projections included at “ —Certain Financial Projections” beginning on page 53. Mr. Eberle updated the Board of Directors on management presentations that had been given that week and upcoming

scheduled presentations. Representatives of Deutsche Bank summarized the results of their outreach to strategic parties, indicating that Deutsche Bank had contacted seven additional potential strategic acquirors of the Company and that none had expressed interest in entering into an NDA in order to receive non-public information concerning the Company.

During the latter part of November 2021 and early December 2021, several private equity firms contacted Deutsche Bank inquiring whether the Company was considering a sale process. Deutsche Bank did not confirm that the Company was engaged in a sale process or invite participation in a process by these private equity firms, and these private equity firms made no further efforts to engage Deutsche Bank or the Company.

On November 29, 2021, a draft of the merger agreement was uploaded to the data room for all bidders to review, and instructions were provided for a markup to be included with bids due on December 6, 2021. This initial draft proposed a go-shop period and lower termination fee for parties identified during the go-shop period. This initial draft did not include a financing contingency; however, given the expectation that bidders (all of whom were then anticipated to be private equity firms) would seek debt financing, this initial draft proposed that the Company’s ability to obtain specific performance to consummate the Merger would be contingent on the availability of a bidder’s debt financing and that if specific performance were not available, the Company’s recourse would be limited to a reverse termination fee. In addition, the draft proposed full acceleration of all Company equity awards at closing. The instructions for the bids due on December 6, 2021 referred bidders to capitalization assumptions contained in the virtual data room, which capitalization assumptions included fully diluted capitalization of approximately 47.4 million shares as of September 30, 2021 and described additional shares to be issued in the ordinary course of business prior to the closing pursuant to equity awards to certain recent or prospective new employees and under the second tranche of the Company’s fiscal year 2022 equity awards to non-named executive officer employees.

On December 2, 2021, Party F submitted a written expression of interest addressed to the Company CEO and the Chairman of the Board of Directors, indicating its interest in participating in the process with respect to a potential transaction. The expression of interest did not include a specific proposed valuation. Party F entered into an NDA with the Company on December 4, 2021 and subsequently received a management presentation from the Company, access to the data room and the draft merger agreement on December 6, 2021. However, Party F did not make a further proposal to acquire the Company. Also on December 2, 2021, a representative of Party G informed Mr. Eberle that it was no longer interested in making a proposal to acquire the Company given the increase in the Company’s stock price following the Company’s announcement of the formation of the Strategy Committee. A representative of Party G subsequently sent an email to Mr. Eberle on December 8, 2021 confirming that Party G would not be making a proposal to acquire the Company on the timeline suggested by the Company but would seek to line up the necessary resources and approvals to further engage after the holidays.

On December 7, 2021, Thoma Bravo submitted an updated written indication of interest, with a per share value of $56.50. Thoma Bravo requested exclusivity for a seven-day period to negotiate a transaction. Thoma Bravo also provided an equity commitment letter from Thoma Bravo Fund XV, L.P. covering 100% of the consideration payable in the Merger, and a markup of the draft merger agreement, which markup proposed the following material revisions: eliminating the go-shop period and lower termination fee for parties identified during the go-shop period, adding a quantitative threshold for the accuracy of the Company’s capitalization representations as a condition to closing, eliminating the requirement that debt financing be available in order for the Company to obtain specific performance to consummate the Merger (subject to the satisfaction of other conditions) and eliminating a reverse termination fee, adding a cap on post-termination damages, adding expense reimbursement by the Company in the event of a termination in which a termination fee could in the future become payable by the Company, expanding Thoma Bravo’s termination rights and the circumstances triggering payment of a termination fee by the Company, and eliminating acceleration of Company equity awards (other than as provided by existing plans and award agreements) such that unvested awards would be converted into time-based cash awards with their existing vesting schedule; and including certain modifications to the overall

suite of representations, warranties and covenants to be provided by each party under the merger agreement. This indication of interest assumed fully diluted capitalization of the Company no greater than approximately 47.4 million shares.

On December 7, 2021, the Board of Directors held a meeting, with members of the Company’s senior management and representatives of Deutsche Bank, Skadden and WilmerHale in attendance, as well as a representative from the Company’s strategic communications advisor, Joele Frank. Representatives of Deutsche Bank updated the Board of Directors on the updated proposal submitted by Thoma Bravo, indicated that an updated proposal was expected from Party B soon, noted that the remaining private equity firms that had received presentations and due diligence material had indicated that they were not interested in pursuing a transaction with the Company (and the reasons conveyed by those entities, which included concerns about future organic growth opportunities, focusing on other transactions, and investment theses being challenged through diligence), and noted that no serious interest had been expressed by the strategic companies to which Deutsche Bank had initiated outreach. The Board of Directors discussed the proposal from Thoma Bravo and directed Deutsche Bank to inform Thoma Bravo that the Company would respond after the Board of Directors’ meeting to be held the following day. The Board of Directors also considered and approved the Company’s five-year financial model that had been reviewed with the Board of Directors at the November 17 meeting. This financial model is identical, other than immaterial differences, to the projections included at “ —Certain Financial Projections” beginning on page 53.

On December 8, 2021, representatives of Deutsche Bank and Party B held a phone conversation whereby Party B continued to indicate its interest in acquiring the Company but expressed the necessity to continue its due diligence into January 2022.

Later on December 8, 2021, the Board of Directors held a meeting, with members of the Company’s senior management and representatives of Deutsche Bank, Skadden and WilmerHale in attendance. Representatives of Deutsche Bank updated the Board of Directors on discussions with Party B, its continued interest in the Company and the additional time that Party B had requested to conduct further diligence before submitting an updated written proposal. Representatives of Deutsche Bank also presented an analysis of Thoma Bravo’s bid, and representatives of Skadden described generally the status of the merger agreement negotiations. The Board of Directors instructed the representatives of Deutsche Bank to request Thoma Bravo to increase its bid and express willingness to work to finalize negotiations on the timeframe proposed by Thoma Bravo if such an increase were acceptable to the Board of Directors, but to resist exclusivity in light of ongoing discussions with Party B.

On December 9, 2021, Thoma Bravo submitted an updated written offer, described as its “best and final” offer, of $57.00 per share, which was also conditioned on a seven-day exclusivity period (which would automatically extend for an additional seven days unless terminated by either party at the end of the initial period).

Later on December 9, 2021, the Board of Directors held a meeting, with members of the Company’s senior management and representatives of Deutsche Bank, Skadden and WilmerHale in attendance. Representatives of Deutsche Bank described the updated bid from Thoma Bravo and the communication regarding Thoma Bravo’s bid and eagerness to finalize the transaction. Representatives of Skadden reviewed legal considerations pertaining to the Board of Directors’ consideration of a sale of the Company, and the Board of Directors discussed the opportunities, risks and challenges of remaining an independent public company as compared to being acquired. The Board of Directors discussed the financial and legal terms of the proposal, and authorized the Company to enter into an exclusivity agreement with Thoma Bravo and to proceed to finalize negotiations with respect to their proposal. Later that day, representatives of Skadden and representatives of Kirkland & Ellis LLP (“Kirkland”), counsel to Thoma Bravo, exchanged signatures from their respective clients on an agreed-upon seven day exclusivity agreement. Thereafter, representatives from Kirkland and Skadden spoke regarding next steps, and representatives from Kirkland indicated that Thoma Bravo would require voting agreements from members of the Board of Directors (including Mr. Eberle) and Clearfield. Following that discussion, also on December 9, 2021, Kirkland provided Skadden with a form of the proposed voting agreement.

Also on December 9, 2021, Bloomberg reported that the Company was exploring a potential sale and other options with assistance from Deutsche Bank and had attracted interest from private equity buyers. The Company did not comment on this report.

During the period following the Company’s entry into an exclusivity agreement with Thoma Bravo on December 9, 2021 through the public announcement of the Merger on December 17, 2021, approximately nine private equity firms or financial advisors purporting to represent possible buyers contacted Deutsche Bank inquiring as to whether the Company was exploring a sale transaction, and Deutsche Bank did not engage with any of these parties given the Company’s exclusivity agreement with Thoma Bravo. However, no proposals were made by any of these third parties.

During the period following the Company’s entry into an exclusivity agreement with Thoma Bravo, representatives of the Company had discussions with representatives of Thoma Bravo relating to Thoma Bravo’s ongoing due diligence.

On December 12, 2021, representatives of Skadden sent proposed revisions to the Kirkland draft of the merger agreement and the equity commitment letter, which proposed the following material revisions: specifying the amount of the termination fee payable by the Company, increasing the quantitative threshold for the accuracy of the Company’s capitalization representations as a condition to closing, increasing the cap on post-termination damages, limiting certain of Thoma Bravo’s termination rights and the circumstances triggering payment of a termination fee by the Company, and providing for 30 months of accelerated vesting (which includes the existing 12 month entitlement under the Company’s 2019 equity plan for equity awards, with unvested awards being converted into time-based cash awards with their existing vesting schedule pulled forward by 30 months); and including certain modifications to the overall suite of representations, warranties and covenants to be provided by each party under the merger agreement. Also on December 12, 2021, Skadden shared the proposed form of voting agreement with members of the Board of Directors.

On December 13, 2021, representatives of SRZ provided comments on the voting agreement with Clearfield to Skadden, and Skadden provided such comments to Kirkland.

On December 14, 2021, Skadden received markups of the merger agreement and the equity commitment letter from Kirkland, which proposed the following material revisions: decreasing the quantitative threshold for the accuracy of the Company’s capitalization representations as a condition to closing, decreasing the cap on post-termination damages, altering the accelerated vesting proposed by the Company (in addition to the existing 12 month entitlement under the Company’s 2019 equity plan for equity awards) in a manner that meaningfully decreased the overall level of acceleration of equity awards versus the Company’s proposal, capping the number of times that the Company could adjourn or postpone the stockholder meeting without Thoma Bravo’s consent, requesting additional information with respect to and/or limiting the Company’s ability to issue equity awards to certain recent or prospective new employees and to issue the second tranche of its fiscal year 2022 equity awards to non-named executive officer employees in the ordinary course of business prior to the closing; and including certain modifications to the overall suite of representations, warranties and covenants to be provided by each party under the merger agreement. Also on December 14, 2021, Skadden sent additional proposed revisions to the voting agreement to Kirkland and to SRZ. Later that day, Kirkland returned the draft voting agreement with non-substantive revisions.

On December 15, 2021, Skadden sent a markup of the merger agreement and a revised draft of the disclosure schedules to the merger agreement to Kirkland, reflecting resolution of issues that Skadden and Kirkland had discussed on telephone calls and over email, including with respect to the specific regulatory approvals required for completion of the Merger, the amount of the cap on post-termination damages, the agreed treatment of Company equity awards in the transaction, the Company’s ability to issue equity awards to certain recent or prospective new employees and to issue the second tranche of its fiscal year 2022 equity awards to non-named executive officer employees in the ordinary course of business prior to the closing, and the Company’s flexibility

to determine quarterly bonuses in the ordinary course of business prior to the closing (including the amount for the current calendar quarter available to be paid to the Chief Financial Officer prior to December 31, 2021 as described under “—Interests of Bottomline’s Directors and Executive Officers in the Merger” beginning on page 55). Skadden and Kirkland continued to confer and exchange drafts in order to finalize the merger agreement, voting agreement and disclosure schedules, until agreement on the final execution version was reached. Also on December 15, 2021, Company management provided revised capitalization information to Thoma Bravo, reflecting fully diluted capitalization of the Company at September 30, 2021 of approximately 45 million shares.

On December 16, 2021, the Board of Directors held a meeting, with members of the Company’s senior management and representatives of Deutsche Bank, Skadden and WilmerHale in attendance. Mr. Eberle and representatives of Deutsche Bank and Skadden provided the Board of Directors with an update on discussions and the resolution of open issues in the merger agreement. Representatives of Skadden described to the Board of Directors the relationships disclosure that had been provided by Deutsche Bank in November 2021, with respect to any relationships between Deutsche Bank and the potential bidders. This disclosure showed that Deutsche Bank received no material fees from Thoma Bravo since the beginning of 2021. Representatives of Deutsche Bank reviewed with the Board of Directors their financial analyses, summarized below in the section entitled “ —Opinion of Bottomline’s Financial Advisor” beginning on page 46.47. At the request of the Board of Directors, representatives of Deutsche Bank rendered the oral opinion of Deutsche Bank, which was subsequently confirmed by delivery of a written opinion, dated December 16,17, 2021, to the Board of Directors, and attached to this proxy statement as Annex B, to the effect that, as of such date and subject to and based on the various assumptions made, procedures followed, matters considered and qualifications and limitations of the review set forth in the written opinion, the merger consideration to be received by the holders of Bottomline common stock pursuant to the merger agreement was fair, from a financial point of view, to such holders. Representatives of Skadden also described in detail the final terms of the merger agreement. After considering the proposed terms of the merger agreement and taking into consideration a variety of factors, including those described in “—Recommendation of the Board of Directors and Reasons for the Merger—Reasons for the Merger” beginning on page 41,42, the Board of Directors unanimously (1) adopted and declared advisable the merger agreement and the transactions contemplated by the merger agreement, (2) declared that it is in the best interests of the Company and its stockholders that the Company enter into the merger agreement and consummate the transactions contemplated by the merger agreement, in each case on the terms and subject to the conditions set forth in the merger agreement, (3) declared that the terms of the merger agreement are fair to the Company and its stockholders and (4) subject to the provisions of the merger agreement, recommended that the Company’s stockholders approve the merger agreement, and directed that the merger agreement be submitted for consideration by Company stockholders at the Company special meeting.

On December 17, 2021, the Company issued a press release and filed a Form 8-K announcing the entry into the Merger Agreement and related matters.

Recommendation of the Board of Directors and Reasons for the Merger

Recommendation of the Board of Directors

The Board of Directors has unanimously (1) adopted and declared advisable the Merger Agreement and the transactions contemplated by the Merger Agreement; (2) declared that it is in the best interests of Bottomline and its stockholders that Bottomline enter into the Merger Agreement and consummate the transactions contemplated by the Merger Agreement, in each case on the terms and subject to the conditions set forth in the Merger Agreement; and (3) declared that the terms of the Merger Agreement are fair to Bottomline and its stockholders.

The Board of Directors unanimously recommends that you vote (1) “FOR” the adoption of the Merger Agreement; (2) “FOR” the adjournment of the Special Meeting, if necessary or appropriate, to solicit additional proxies if there are insufficient votes to adopt the Merger Agreement at the time of the Special Meeting; and (3) “FOR” the proposal to approve, by non-binding, advisory vote, compensation that will or may become payable by Bottomline to its named executive officers in connection with the Merger.

Reasons for the Merger

In evaluating the Merger Agreement and the transactions contemplated thereby, the Board of Directors consulted with outside legal counsel, its financial advisor and Bottomline’s senior management. In recommending that Bottomline’s stockholders vote in favor of adoption of the Merger Agreement, the Board of Directors considered numerous positive factors relating to the Merger Agreement, the Merger and the other transactions contemplated by the Merger Agreement, including the following material factors (which factors are not necessarily presented in order of relative importance):

In the course of reaching the determinations and decisions and making the recommendation described above, the Board of Directors, in consultation with Bottomline’s senior management, outside legal counsel and financial advisor, considered the risks and potentially negative factors relating to the Merger Agreement, the Merger and the other transactions contemplated by the Merger Agreement, including the following material factors (which factors are not necessarily presented in order of relative importance):

The Board of Directors believed that, overall, the potential benefits of the Merger to Bottomline’s stockholders outweighed the risks and uncertainties of the Merger.

The foregoing discussion of factors considered by the Board of Directors contains the material factors considered by the Board of Directors, but is not in any way intended to be exhaustive. In light of the variety of factors considered in connection with its evaluation of the Merger, the Board of Directors did not find it practicable to, and did not, quantify or otherwise assign relative weights to the specific factors considered in reaching its determinations and recommendations. Each member of the Board of Directors applied his or her own business judgment to the process and may have given different weight to different factors. The Board of Directors did not undertake to make any specific determination as to whether any factor or any particular aspect of a factor supported or did not support its ultimate determination. The Board of Directors based its recommendation on the totality of the information presented.

Opinion of Bottomline’s Financial Advisor

Pursuant to an engagement letter dated as of September 20, 2021, Deutsche Bank acted as financial advisor to the Board of Directors in connection with the Merger. At the December 16, 2021 meeting of the Board of Directors, Deutsche Bank delivered its opinion, subsequently confirmed in writing, to the effect that, as of the date of such opinion, based upon and subject to the assumptions, limitations, qualifications and other conditions set forth in the opinion, the Per Share Merger Consideration was fair, from a financial point of view, to holders of Bottomline’s common stock.

The full text of Deutsche Bank’s written opinion, dated as of December 17, 2021, which sets forth, among other things, the assumptions made, matters considered and limitations, qualifications and conditions of the review undertaken by Deutsche Bank in connection with its opinion, is attached as Annex B to this proxy statement and is incorporated herein by reference in its entirety. Deutsche Bank’s opinion has been approved and authorized for issuance by a Deutsche Bank fairness opinion review committee and is addressed to, and is for the use and benefit of, the Board of Directors in connection with and for the purpose of its evaluation of the Merger. Deutsche Bank’s opinion is limited to the fairness of the Per Share Merger Consideration, from a financial point of view, to the holders of Bottomline’s common stock as of the date of the opinion. Deutsche Bank’s opinion does not address any other terms of the Merger or the Merger Agreement, nor does it address the terms of any other agreement entered into or to be entered into in connection with the Merger. Deutsche Bank was not asked to, and Deutsche Bank’s opinion did not, address the fairness of the Merger, or any consideration received in connection therewith, to the holders of any other class of securities, creditors or other constituencies of the Company, nor did it address the fairness of the contemplated benefits of the Merger. Deutsche Bank expressed no opinion as to the merits of the

In connection with Deutsche Bank’s role as financial advisor to the Board of Directors, and in arriving at its opinion, Deutsche Bank has, among other things, reviewed certain publicly available financial and other information concerning the Company and certain internal analyses, financial forecasts and other information relating to the Company prepared and furnished to Deutsche Bank by the management of the Company and approved for Deutsche Bank’s use by the Company. Deutsche Bank also held discussions with certain senior officers of the Company regarding the businesses and prospects of the Company. In addition, Deutsche Bank has:

In preparing its opinion, Deutsche Bank did not assume responsibility for the independent verification of, and did not independently verify, any information, whether publicly available or furnished to it, concerning the Company, including, without limitation, any financial information considered in connection with the rendering of its opinion. Accordingly, for purposes of its opinion, with the knowledge and permission of the Board, Deutsche Bank assumed and relied upon the accuracy and completeness of all such information. Deutsche Bank did not conduct a physical inspection of any of the properties or assets and did not prepare, obtain or review any independent evaluation or appraisal of any of the assets or liabilities (including any contingent, derivative or off-balance sheet assets or liabilities) of the Company or any of its respective subsidiaries, nor did Deutsche Bank evaluate the solvency or fair value of the Company under any law relating to bankruptcy, insolvency or similar matters. With respect to the financial forecasts made available to Deutsche Bank and used in its analyses, Deutsche Bank, with the knowledge and permission of the Board of Directors, assumed that such forecasts had been reasonably prepared on bases reflecting the best currently available estimates and judgments of the management of the Company as to the matters covered thereby. In rendering its opinion, Deutsche Bank expressed no view as to the reasonableness of such forecasts and projections or the assumptions on which they are based. Deutsche Bank’s opinion was necessarily based upon the economic, market and other conditions as in effect on, and the information made available to Deutsche Bank as of, the date of such opinion. Deutsche Bank expressly disclaimed any undertaking or obligation to advise any person of any change in any fact or matter affecting Deutsche Bank’s opinion of which it becomes aware after the date of the opinion.

rendering its opinion described above. The following summary, however, does not purport to be a complete description of the financial analyses performed by Deutsche Bank, nor does the order of the analyses described below represent the relative importance or weight given to those analyses by Deutsche Bank or the Board. Considering the data below without considering the full narrative description of the financial analyses, including the methodologies and assumptions underlying the analyses, could create a misleading or incomplete view of Deutsche Bank’s financial analyses. Certain financial, comparative and other analyses summarized below include information presented in tabular format. The tables must be read together with the text of each summary and are alone not a complete description of Deutsche Bank’s financial analyses. Except as otherwise noted, the following quantitative information, to the extent that it is based on market data, is based on market data as it existed on or before December 15, 2021, and is not necessarily indicative of current market conditions. In performing its analyses, Deutsche Bank made numerous assumptions with respect to industry performance, general business and economic conditions and other matters, many of which are beyond the control of the Company. None of the Company, Parent, Merger Sub, Deutsche Bank or any other person assumes responsibility if future results are materially different from those discussed. Any estimates contained in these analyses are not necessarily indicative of actual values or predictive of future results or values, which may be significantly more or less favorable than as set forth below. In addition, analyses relating to the value of the businesses do not purport to be appraisals or to reflect the prices at which the businesses could actually be sold.

Discounted Cash Flow Analysis

Deutsche Bank performed a discounted cash flow analysis of the Company on a standalone basis using financial forecasts, data and other information provided by the Company’s management to calculate a range of implied equity values per share of the Company discounted to December 15, 2021.

In performing the discounted cash flow analysis, Deutsche Bank applied a range of discount rates of 9.00% to 10.00% to the sum of (i) unlevered free cash flows estimated to be generated by the Company for the fiscal years 2022 to 2031, as calculated based on financial forecasts and data provided by the Company’s management and (ii) estimated terminal values of the Company calculated using perpetuity growth rates ranging from 2.50% to 3.50%. For purposes of its analysis, Deutsche Bank calculated unlevered free cash flow as (a) adjusted earnings before interest, taxes, depreciation and amortization (which we refer to as “Adjusted EBITDA”), less (b) capital expenditures, less (c) stock based compensation, less (d) cash taxes, plus (e) increase (decrease) in deferred revenue, and less (f) increase (decrease) in working capital, in each case as provided to Deutsche Bank by the Company’s management.

prospects of the Company and the selected comparable companies that could affect the values of the Company in order to provide a context in which to consider the results of the quantitative analysis for Company. Deutsche Bank selected comparable companies with businesses in the categories of financial software and payment technology.

To calculate the trading multiples for the selected companies, Deutsche Bank used publicly available information concerning historical and projected financial performance, including published historical financial information and forecasted estimates based on widely used industry data and research providers and public filings made by the selected companies. Using such financial information, Deutsche Bank reviewed for each of these companies, among other things: (i) the ratio of enterprise value to Adjusted EBITDA (which we refer to as “EV/EBITDA”) and (ii) the ratio of enterprise value to revenue (which we refer to as “EV/Revenue”). The companies reviewed and analysis indicated the following, with multiples based on publicly available research analyst median calendar year 2022 estimates:

Bank derived and compared, among other things, the mean and median values of multiples for the ratio of total enterprise value to last-twelve-months Adjusted EBITDA (which we refer to as “TEV/LTM EBITDA”). To calculate the comparative data for the selected transactions, Deutsche Bank used publicly available information from public filings, FactSet and Wall Street research. The transactions reviewed and analysis indicated the following:

Based upon the results of the selected precedent transactions analysis, Deutsche Bank calculated ranges of estimated implied value per share of Bottomline’s common stock by applying multiples of TEV/EBITDA of 20.0x to 24.0x to the Company’s management estimates of last twelve months Adjusted EBITDA, resulting in a range of implied values of $42.49 to $51.01 per share of Bottomline’s common stock.

Deutsche Bank noted that the analyst price targets were presented merely for reference purposes only, and were not relied upon for valuation purposes.

Miscellaneous

The foregoing summary is not a comprehensive description of all analyses performed and factors considered by Deutsche Bank in connection with preparing its opinion. The preparation of a fairness opinion is a complex process involving the application of subjective business judgment in determining the most appropriate and relevant methods of financial analysis and the application of those methods to the particular circumstances and, therefore, is not readily susceptible to a summary description. Deutsche Bank believes that its analyses must be considered as a whole and that considering any portion of such analyses and of the factors considered without considering all analyses and factors could create a misleading view of the process underlying the opinion. In arriving at its fairness determination, Deutsche Bank did not assign specific weights to any particular analyses.

In conducting its analyses and arriving at its opinion, Deutsche Bank utilized a variety of generally accepted valuation methods. The analyses were prepared solely for the purpose of enabling Deutsche Bank to provide its opinion to the Board as to the fairness, from a financial point of view, to the holders of Bottomline’s common stock, of the Per Share Merger Consideration. Analyses based on estimates or forecasts of future results are not necessarily indicative of actual past or future values or results, which may be significantly more or less favorable than suggested by such analyses. Because such analyses are inherently subject to uncertainty, being based upon numerous factors or events beyond the control of the Company or its advisors, neither the Company nor Deutsche Bank nor any other person assumes responsibility if future results or actual values are materially different from these forecasts or assumptions.

The terms of the Merger were determined through negotiations between the Company and Parent and were approved by the Board of Directors. Although Deutsche Bank provided advice to the Board during the course of these negotiations, the decision to enter into the Merger was solely that of the Board of Directors. As described above, the opinion and presentation of Deutsche Bank to the Board of Directors were only one of a number of factors taken into consideration by the Board in making its determination to approve the Merger. Deutsche

Regardless of whether the Merger is consummated, the Company has agreed to reimburse Deutsche Bank for reasonable and documented fees, expenses and disbursements of Deutsche Bank’s counsel and all of Deutsche Bank’s reasonable and documented travel and other out-of-pocket expenses incurred in connection with the Merger or otherwise arising out of the engagement of Deutsche Bank under the engagement letter provided that if such fees exceed $100,000 in the aggregate, such excess fees will only be reimbursed if incurred with the prior written consent of the Company. The Company has also agreed to indemnify Deutsche Bank and certain related persons to the full extent lawful against certain liabilities arising out of its engagement or the Merger.

Deutsche Bank is an internationally recognized investment banking firm experienced in providing advice in connection with mergers and acquisitions and related transactions. Deutsche Bank is an affiliate of Deutsche Bank AG, which, together with its affiliates, are referred to in this proxy statement as the DB Group. One or more members of the DB Group have, from time to time, provided, and are currently providing, commercial banking (including extension of credit) and other financial services to Parent or its affiliates for which they have received, and in the future may receive, compensation, including (i) acting as joint arranger for an entity affiliated with Thoma Bravo, L.P., an affiliate of Parent, on a debt financing transaction in February 2019, (ii) acting as joint bookrunner for an entity affiliated with Thoma Bravo, L.P. and lender on a debt financing transaction in November 2020, (iii) receiving deferred fees from an entity affiliated with Thoma Bravo, L.P. in June 2021 in connection with a SPAC initial public offering and (iv) acting as joint bookrunner for an entity affiliated with Thoma Bravo, L.P. on debt financing transactions in October 2020 and January, March, April, May and September 2021. In addition, the DB Group may also provide investment and commercial banking services to Parent and the Company in the future, for which Deutsche Bank would expect the DB Group to receive compensation. In the ordinary course of business, members of the DB Group may actively trade in the securities and other instruments and obligations of Parent, the Company and their respective affiliates for their own accounts and for the accounts of their customers. Accordingly, the DB Group may at any time hold a long or short position in such securities, instruments and obligations.

The following table summarizes the Financial Projections prepared as described above.

(amounts in millions)

Unlevered Free Cash Flows

Additionally, at the direction of Bottomline management, Deutsche Bank calculated, based on the five-year financial projections provided by Bottomline management, unlevered free cash flows for fiscal years 2022 through 2031 for use in connection with its financial analysis.

The following is a summary of the calculation of unlevered free cash flows, which were prepared as described above, reviewed by and approved by Bottomline management, and used by Deutsche Bank for the purposes of its financial analyses, and which are defined as Adjusted EBITDA, less cash taxes, less capital expenditures, less stock-based compensation, plus increase (decrease) in deferred revenue, less increase (decrease) in working capital.

(amounts in millions)

addition, the Financial Projections cover multiple years and such information by its nature becomes less predictive with each successive year. Therefore, the Financial Projections included in this proxy statement should not be relied on as necessarily predictive of actual future events nor construed as financial guidance.

Bottomline shareholders are urged to review the Company’s most recent SEC filings for a description of risk factors with respect to the Company’s business. You should read “Cautionary Statement Regarding Forward-Looking Statements” for additional information regarding the risks inherent in forward-looking information such as the Financial Projections and “Where You Can Find More Information”.

The Financial Projections were not prepared with a view toward complying with GAAP (including because certain metrics are non-GAAP measures, and the forecasts contained therein do not include footnote disclosures as may be required by GAAP), the published guidelines of the SEC regarding projections or the guidelines established by the American Institute of Certified Public Accountants for preparation and presentation of prospective financial information. Neither the Company’s independent registered public accounting firm, nor any other independent accountants, have compiled, examined, or performed any procedures with respect to the Financial Projections, nor have they expressed any opinion or any other form of assurance on the Financial Projections or the achievability of the results reflected in the Financial Projections, and they assume no responsibility for, and disclaim any association with, the Financial Projections. Non-GAAP measures should not be considered in isolation from, or as a substitute for, financial information presented in compliance with GAAP, and non-GAAP measures such as those used in the Financial Projections may not be comparable to similarly titled amounts used by other companies or persons.

The non-GAAP measures set forth above should not be considered a substitute for, or superior to, financial measures determined or calculated in accordance with U.S. GAAP. Financial measures included in forecasts provided to a financial advisor and a board of directors in connection with a business combination transaction, such as the Financial Projections, are excluded from the definition of “non-GAAP financial measures” under applicable SEC rules and regulations. As a result, the Financial Projections are not subject to SEC rules regarding disclosures of non-GAAP financial measures, which would otherwise require a reconciliation of a non-GAAP

Philip Hilal, a director of Bottomline, is also the Founder and Chief Investment Officer of Clearfield Capital Management LP. As of [December 14, 2021],January 24, 2022, Mr. Hilal beneficially owned [935,000]935,000 shares (approximately [2.1%]2.1%) of Bottomline’s common stock (which includes shares that Mr. Hilal may be deemed to beneficially own by virtue of his positions at Clearfield Capital Management LP). As of [December 14, 2021],January 24, 2022, Clearfield Capital Management LP beneficially owned [925,000]925,000 shares (approximately [2.1%]2.1%) of Bottomline’s common stock.

Treatment of Equity-Based Awards

The Merger Agreement provides that immediately prior to, and subject to the occurrence of, the Effective Time, (1) for any unvested restricted stock award or unvested restricted stock unit award the vesting of which is conditioned upon both time-based vesting and the attainment of performance conditions and that remains outstanding and subject to such performance vesting conditions as of immediately prior to the Effective Time, the number of shares of Bottomline common stock subject to such unvested restricted stock award or unvested restricted stock unit award will be fixed at the Effective Time based upon the target level of performance, and (2) each outstanding unvested stock option and each outstanding unvested restricted stock award and unvested restricted stock unit award will be credited the Additional Vesting Credit. The Additional Vesting Credit includes the 12 months of “change in control” accelerated vesting provided in Bottomline’s 2019 Stock Incentive Plan, as amended and is without limitation of any more favorable vesting provisions in any other plan or agreement between Bottomline and any employee (described below for our named executive officers, where applicable).

Treatment of Stock Options in the Merger

As of [December 14, 2021],January 24, 2022, there were [1,051]1,051 outstanding options to acquire Bottomline common stock, all of which options were both vested and “in-the-money,” meaning that they have an exercise price less than $57.00 per share. Bottomline’s directors and executive officers held none of such stock options. As of the Effective Time, each option that is outstanding will be converted into the right to receive an amount in cash (subject to any applicable tax withholding) equal to the product of (1) the excess of $57.00 over the exercise price per share of Bottomline common stock underlying such stock option; and (2) the total number of shares of Bottomline common stock subject to such option.

equal to the product of (i) $57.00, multiplied by (ii) the number of shares of Bottomline common stock subject to such restricted stock unit award. Each other outstanding restricted stock unit award will be converted into a right to receive an amount in cash, without interest, equal to the product of (i) $57.00, multiplied by (ii) the number of shares of Bottomline common stock subject to such restricted stock unit award, which amount will, subject to the holder’s continued service with Bottomline, Parent or an affiliate through the applicable vesting date and vest at the same time and on the same terms as the restricted stock unit to which such cash amount relates would have vested pursuant to its terms (except that any applicable performance conditions will be deemed to have been achieved at target levels and after giving effect to Additional Vesting Credit). Additionally, under Bottomline’s 2019 Stock Incentive Plan, if the holder’s employment is terminated other than for cause or by the holder for good reason within two years of the Effective Time, the cash amount to which such restricted stock unit award relates will immediately vest..

Employee Stock Purchase Plan

Pursuant to the Merger Agreement, no new offering period or purchase period will be commenced following the date of the Merger Agreement under the ESPP, and the offering period or purchase period in effect on the date of the Merger Agreement will be the final offering period or purchase period under the Employee Stock Purchase Plan. Participants will not be permitted to increase the amount of their payroll deduction elections under the ESPP during the final offering period or purchase period, and no new individuals will be permitted to commence participation in the ESPP prior to the Effective Time. The ESPP will be terminated immediately prior to the Effective Time.

Equity Interests of Bottomline’s Executive Officers and Non-Employee Directors

The following table sets forth the number of shares of Bottomline common stock and the number of shares of Bottomline common stock underlying restricted stock awards and restricted stock unit awards that, as of [December 14, 2021],January 24, 2022, were held by each of Bottomline’s executive officers (including the named executive officers) and non-employee directors, in each case that either were then-currently vested or that will or may vest in connection with the Merger. The table also sets forth the values of these shares and equity awards based on the $57.00 Per Share Merger Consideration.

Potential Severance Payments and Benefits

Employment, Service and Retention Agreements

Bottomline is party to employment agreements or similar arrangements with Mr. Eberle, Mr. Bowden, Mr. DeLuca and Mr. Savory which provide for certain benefits upon a “change in control”, including the treatment of unvested equity awards and in certain instances severance benefits. Under each of the agreements a change in control will occur upon the closing of the Merger. The following descriptions are qualified by reference to the full agreements as previously filed with the Securities and Exchange Commission.

Robert A. Eberle Employment Agreement

Bottomline is party to an employment agreement with Mr. Eberle which provides for certain payments and benefits that will or may be payable upon or in connection with the closing of the Merger. Under the employment agreement with Mr. Eberle, the closing of the Merger will constitute a “change in control” of Bottomline; and the employment agreement provides that upon a change in control, Mr. Eberle’s restricted stock awards will vest in full. The employment agreement also provides that if Mr. Eberle’s employment is terminated during a potential change in control (Bottomline’s entry into the Merger Agreement resulted in such a potential change in control), either by Mr. Eberle as a result of an involuntary termination or by Bottomline without cause (in each case as defined in the employment agreement), all of his restricted stock awards will vest in full. In the event of such a termination either during a potential change in control or following a change in control, Mr. Eberle will be entitled to receive a lump sum severance payment equal to three times the sum of (i) Mr. Eberle’s then annual salary and (ii) the maximum amount of any bonus Mr. Eberle was eligible to earn for the then-current fiscal year, as well as continuation of benefits for a period of 24 months. If Mr. Eberle is not continuing his employment with the Company following closing, he will be entitled to these payments immediately prior to the closing.

the premiums for health continuation coverage and the amount for which Mr. Bowden would otherwise be responsible with respect to the medical and dental coverage elected until the earlier of 12 months after the date of termination and the date on which Mr. Bowden becomes covered under another employer insurance plan that provides substantially similar in the aggregate or greater coverage than the Company’s health plans.

Pursuant to the Merger Agreement, if Mr. Bowden remains employed by the Company at the time of the closing, he will be entitled to the Additional Vesting Credit with respect to his outstanding equity awards as well as full vesting of his remaining unvested equity awards due to his having “good reason” as of the effective date.

Bottomline is also party to an employment agreement with Mr. Bowden; however, all payments and benefits payable in connection with the Merger would be provided pursuant to Mr. Bowden’s retention agreement described above.

Norman J. DeLuca Employment Agreement

Bottomline is party to an employment agreement with Mr. DeLuca, which provides that any restricted stock granted to Mr. Deluca will vest in full upon a change in control. In addition, if Mr. DeLuca’s employment is terminated by Bottomline without cause, either before or after a change in control, he will be provided six months’ salary and benefits, and a lump sum payment equal to 50% of his annual bonus opportunity pursuant to Bottomline’s severance practice with respect to senior executives.

Nigel K. Savory Service Agreement

Bottomline is party to a Service Agreement with Mr. Savory. The Service Agreement generally provides that during a transition period running from March 12, 2022 until June 1, 2023, either Bottomline or Mr. Savory may provide written notice that the working arrangement pursuant to the service agreement is either not working as desired or not one the party desires to continue, subject to certain exceptions in the case of Mr. Savory. In the event that either Bottomline or Mr. Savory exercises its right to serve such notice (the “transition notice”) during the transition period, then, subject to Mr. Savory’s execution of a release of claims in favor of the Company, (i) Mr. Savory will be entitled to severance in the form of 12 months’ base salary continuation (subject to certain

remaining unvested equity awards upon a qualifying termination of employment within two years of the effective date. If Mr. Savory is serving as a strategic advisor at the time of closing, he will be entitled to the Additional Vesting Credit with respect to his outstanding equity awards.

John F. Kelly Special Advisor and Transition Agreement

Bottomline is also party to a Special Advisor and Transition Agreement with Mr. Kelly, under which Mr. Kelly continues to serve as Special Advisor to Bottomline following the termination of his employment that occurred on August 24, 2021, and pursuant to which his stock awards will continue to vest through August 24, 2022 and are thus entitled to the Additional Vesting Credit provided in the Merger Agreement, which will result in full vesting of his remaining awards.

Stock Incentive Plans

In addition to the change in control provisions in such individual employment arrangements, our stock incentive plans contain provisions that are applicable to all plan participants regarding the consequences of a “Change in Control Event” (which will occur upon the Effective Time). Generally, the plans provide that the vesting schedule of any unvested restricted stock award or restricted stock unit award would be accelerated in part such that what would have otherwise become vested on any date within one year after the date of the Change in Control Event would immediately become vested. Additionally, each unvested restricted stock award or restricted stock unit award would immediately become free from all vesting conditions or restrictions if, on or prior to the second anniversary of the date of the consummation of the Change in Control Event, the plan participant’s employment with the Company or the acquiring or succeeding corporation is terminated for Good Reason (as defined in the applicable plan) by the participant or is terminated without Cause (as defined in the applicable plan) by the Company or the acquiring or succeeding corporation. Awards that vest in whole or in part based on specified performance conditions will be deemed satisfied at the target level upon the consummation of the Change in Control Event. Awards continue to be subject to their original service-based vesting requirements (if any) and be accelerated, as applicable, as described in the preceding two sentences of this paragraph. Such

fully vested as a result of either the occurrence of a “change in control” or, for named executive officers who are employed at that time, a qualifying termination; (iv) no named executive officer receives any additional equity grants or retention awards on or prior to the closing; and (v) no named executive officer enters into any new agreement or becomes entitled to, prior to the closing, additional compensation or benefits related to the transactions contemplated by the Merger Agreement.

administrative or investigative (including with respect to matters existing or occurring at or prior to the Effective Time, including the Merger Agreement and the transactions and actions contemplated thereby), arising out of or pertaining to the fact that such person is or was a director or officer of Bottomline or any of its subsidiaries or is or was serving at the request of Bottomline or any of its subsidiaries as a director or officer of another person, whether asserted or claimed at, prior to or after the Effective Time, to the fullest extent permitted under the governing or organizational documents of Bottomline and its subsidiaries and any indemnification or other similar agreements of Bottomline and any of its subsidiaries. In the event of any such claim, action, suit or proceeding, such person will be entitled to advancement of expenses incurred in the defense of any such claim, action, suit or proceeding from the Surviving Corporation in accordance with the organizational documents of the Surviving Corporation in effect on the date of the Merger Agreement; provided that any person to whom expenses are advanced provides an undertaking, if and only to the extent required by the DGCL or the Surviving Corporation’s certificate of incorporation or bylaws to repay such advances if it is ultimately determined by final adjudication that such person is not entitled to indemnification, and the Surviving Corporation will reasonably cooperate in the defense of any such matter.

On December 16, 2021, Parent entered into the Equity Commitment Letter, pursuant to which the Thoma Bravo Fund has committed to purchase, or cause the purchase of, an amount of equity securities of Parent at or immediately prior to the Effective Time equal to the estimated amount of aggregate consideration that will be due and payable at closing. The Equity Commitment Letter provides, among other things, that Bottomline is an express third party beneficiary thereof in connection with Bottomline’s exercise of its rights related to specific performance under the Merger Agreement. The Equity Commitment Letter may not be amended, revoked, modified or terminated, and no provision thereunder may be waived, except by an instrument in writing signed by Parent, Bottomline and the Thoma Bravo Fund. For more information please see the section captioned “The Merger Agreement — Financing,” beginning on page 8788 of this proxy statement.

Under the Merger Agreement, Bottomline agrees to cooperate should Parent attempt to obtain the Debt Financing, if any. For more information please see the section captioned “The Merger Agreement — Financing Cooperation,” beginning on page 8889 of this proxy statement.

Stockholders considering seeking appraisal should be aware that the fair value of their shares as determined pursuant to Section 262 could be more than, the same as or less than the Per Share Merger Consideration.

Under Section 262, where a merger agreement is to be submitted for adoption at a meeting of stockholders, the corporation, not less than twenty days prior to the meeting, must notify each of its stockholders entitled to appraisal rights that appraisal rights are available and include in the notice a copy of Section 262. This proxy statement constitutes Bottomline’s notice to stockholders that appraisal rights are available in connection with the Merger, and the full text of Section 262 is attached to this proxy statement as Annex C. In connection with the Merger, any holder of shares of common stock who wishes to exercise appraisal rights or who wishes to preserve such holder’s right to do so should review Annex C carefully. Failure to strictly comply with the requirements of Section 262 in a timely and proper manner will result in the loss of appraisal rights under the DGCL. A stockholder who loses his, her or its appraisal rights will be entitled to receive the Per Share Merger Consideration. Moreover, because of the complexity of the procedures for exercising the right to seek appraisal of shares of common stock, Bottomline believes that if a stockholder considers exercising such rights, that stockholder should seek the advice of legal counsel.

constitute a demand. A stockholder’s failure to make the written demand prior to the taking of the vote on the adoption of the Merger Agreement at the Special Meeting of Bottomline’s stockholders will constitute a waiver of appraisal rights.

Only a holder of record of shares of common stock is entitled to demand appraisal rights for the shares registered in that holder’s name. A demand for appraisal in respect of shares of common stock should be executed by or on behalf of the holder of record and must reasonably inform Bottomline of the identity of the holder and state that the person intends thereby to demand appraisal of the holder’s shares in connection with the Merger. If the shares are owned of record in a fiduciary capacity, such as by a trustee, guardian or custodian, such demand must be executed by or on behalf of the record owner, and if the shares are owned of record by more than one person, as in a joint tenancy and tenancy in common, the demand should be executed by or on behalf of all joint owners. An authorized agent, including an authorized agent for two or more joint owners, may execute a demand for appraisal on behalf of a holder of record; however, the agent must identify the record owner or owners and expressly disclose that, in executing the demand, the agent is acting as agent for the record owner or owners.

the Surviving Corporation in the case of a petition filed by a stockholder, demanding a determination of the fair value of the shares held by all stockholders entitled to appraisal. The Surviving Corporation is under no obligation, and has no present intention, to file a petition, and holders should not assume that the Surviving Corporation will file a petition or initiate any negotiations with respect to the fair value of the shares of common stock. Accordingly, any holders of shares of common stock who desire to have their shares appraised should initiate all necessary action to perfect their appraisal rights in respect of their shares of common stock within the time and in the manner prescribed in Section 262. The failure of a holder of common stock to file such a petition within the period specified in Section 262 could nullify the stockholder’s previous written demand for appraisal.

Within 120 days after the Effective Time, any holder of shares of common stock who has complied with the requirements for exercise of appraisal rights, or a beneficial owner of shares held in either a voting trust or by a nominee on behalf of such person, will be entitled, upon written request, to receive from the Surviving Corporation a statement setting forth the aggregate number of shares not voted in favor of the adoption of the Merger Agreement and with respect to which Bottomline has received demands for appraisal, and the aggregate number of holders of such shares. The Surviving Corporation must mail this statement to the requesting

exclusion [that] does not encompass known elements of value,” but which rather applies only to the speculative elements of value arising from such accomplishment or expectation. In Weinberger, the Supreme Court of Delaware also stated that “elements of future value, including the nature of the enterprise, which are known or susceptible of proof as of the date of the merger and not the product of speculation, may be considered.” In addition, the Delaware courts have decided that the statutory appraisal remedy, depending on factual circumstances, may or may not be a dissenting stockholder’s exclusive remedy.

Stockholders considering seeking appraisal should be aware that the fair value of their shares as so determined by the Delaware Court of Chancery could be more than, the same as or less than the consideration they would receive pursuant to the Merger if they did not seek appraisal of their shares and that an opinion of an investment banking firm as to the fairness from a financial point of view of the consideration payable in a Merger is not an opinion as to, and does not in any manner address, fair value under Section 262. Although Bottomline believes that the Per Share Merger Consideration is fair, no representation is made as to the outcome of the appraisal of fair value as determined by the Delaware Court of Chancery, and stockholders should recognize that such an appraisal could result in a determination of a value higher or lower than, or the

U.S. Federal Income Tax Consequences of the Merger

The following discussion is a summary of certain U.S. federal income tax consequences of the Merger that are relevant to U.S. Holders and Non-U.S. Holders (each as defined below) of shares of common stock of Bottomline whose shares are converted into the right to receive cash pursuant to the Merger. This discussion is based upon the Code, Treasury Regulations promulgated under the Code, court decisions, published positions of the Internal Revenue Service (the “IRS”), and other applicable authorities, all as in effect on the date of this proxy statement and all of which are subject to change or differing interpretations, possibly with retroactive effect.

discussion, or that a court will not sustain any challenge by the IRS in the event of litigation. Furthermore, no opinion of counsel has been or will be rendered with respect to any tax considerations of the Merger or any related transactions. The use of words such as “will” and “should” in any tax-related discussion contained in this discussion is not intended to convey a particular level of comfort.

pursuant to the Merger may be subject to backup withholding at a rate currently equal to 24%. Backup withholding is not an additional tax. Any amounts withheld under the backup withholding rules may be allowed as a refund or a credit against a U.S. Holder’s U.S. federal income tax liability, provided the required information is timely furnished to the IRS.

applicable waiting period under the HSR Act; and (ii) approval of the change in control relating to Bottomline Payment Services Limited (a U.K.-based subsidiary of Bottomline) by the Financial Conduct Authority in the United Kingdom.

Although we expect that all required regulatory clearances and approvals will be obtained, we cannot assure you that these regulatory clearances and approvals will be timely obtained, obtained at all or that the granting of these regulatory clearances and approvals will not involve the imposition of additional conditions on the completion of the Merger, including the requirement to divest assets, or require changes to the terms of the Merger Agreement. These conditions or changes could result in the conditions to the Merger not being satisfied.

Legal Proceedings Regarding the Merger

On January 19, 2022, a purported stockholder of Bottomline filed a lawsuit in the United States District Court for the Southern District of New York against Bottomline and its directors, captioned Shiva Stein v. Bottomline Technologies, Inc., et al., Case No. 1:22-cv-00481 (the “Stein Complaint”). On January 21, 2022, a purported stockholder of Bottomline filed a lawsuit in the United States District Court for the Southern District of New York against Bottomline and its directors, captioned Jeffrey D. Justice, II v. Bottomline Technologies, Inc., et al., Case No. 1:22-cv-00586 (the “Justice Complaint”). On January 26, 2022, a purported stockholder of Bottomline filed a lawsuit in the United States District Court for the Southern District of New York against Bottomline and its directors, captioned Chau Le v. Bottomline Technologies, Inc., et al., Case No. 1:22-cv-00670 (the “Le Complaint”).

All of the complaints allege that the preliminary proxy statement issued in connection with the Merger omits material information or contains misleading disclosures and that, as a result, (i) all of the defendants violated Section 14(a) of the Exchange Act and (ii) all of Bottomline’s directors violated section 20(a) of the Exchange Act. The Le Complaint also alleges that Bottomline’s directors breached their fiduciary duties of care, loyalty and good faith by, among other things, causing Bottomline to enter into the transactions contemplated by the Merger Agreement as a result of an inadequate sale process, agreeing to preclusive deal mechanisms and filing a materially misleading and incomplete preliminary proxy statement. The Le Complaint also alleges that Bottomline aided and abetted these purported breaches of fiduciary duties.

All of the complaints seek, among other things, (i) injunctive relief preventing the consummation of the transactions contemplated by the Merger Agreement; (ii) rescission or rescissory damages in the event the transactions contemplated by the Merger Agreement have been implemented; (iii) dissemination of a proxy statement that does not omit material information or contain any misleading disclosures; (iv) a declaration that defendants violated Sections 14(a) and/or 20(a) of the Exchange Act (except the Stein Complaint and the Le Complaint) or that Bottomline’s directors violated their fiduciary duties (except the Stein Complaint and the Justice Complaint); (v) to direct the defendants to account to plaintiff for all damages suffered (except the Justice Complaint); and (vi) an award of plaintiff’s expenses, including attorneys’ and experts’ fees.

Bottomline, Parent and Merger Sub believe the claims asserted in each of the complaints are without merit.

Additional lawsuits may be filed against Bottomline, the Board of Directors, Parent and/or Merger Sub in connection with the transactions contemplated by the Merger Agreement and the Proxy Statement.

THE MERGER AGREEMENT

Explanatory Note Regarding the Merger Agreement

The following summary describes the material provisions of the Merger Agreement. The descriptions of the Merger Agreement in this summary and elsewhere in this proxy statement are not complete and are qualified in their entirety by reference to the Merger Agreement, a copy of which is attached to this proxy statement as Annex A and incorporated into this proxy statement by reference. We encourage you to read the Merger Agreement carefully and in its entirety because this summary may not contain all the information about the Merger Agreement that is important to you. The rights and obligations of the parties are governed by the express terms of the Merger Agreement and not by this summary or any other information contained in this proxy statement. Capitalized terms used in this section but not defined in this proxy statement have the meaning ascribed to them in the Merger Agreement.

The representations, warranties, covenants and agreements described below and included in the Merger Agreement (1) were made only for purposes of the Merger Agreement and as of specific dates; (2) were made solely for the benefit of the parties to the Merger Agreement; and (3) may be subject to important qualifications, limitations and supplemental information agreed to by Bottomline, Parent and Merger Sub in connection with negotiating the terms of the Merger Agreement. The representations and warranties may also be subject to a contractual standard of materiality different from those generally applicable to reports and documents filed with the SEC and in some cases were qualified by confidential matters disclosed to Parent and Merger Sub by Bottomline in connection with the Merger Agreement. In addition, the representations and warranties may have been included in the Merger Agreement for the purpose of allocating contractual risk among Bottomline, Parent and Merger Sub rather than to establish matters as facts, and may be subject to standards of materiality applicable to such parties that differ from those applicable to investors. Stockholders are not third-party beneficiaries under the Merger Agreement and should not rely on the representations, warranties, covenants and agreements or any descriptions thereof as characterizations of the actual state of facts or condition of Bottomline, Parent or Merger Sub or any of their respective affiliates or businesses. Moreover, information concerning the subject matter of the representations and warranties may change after the date of the Merger Agreement. In addition, you should not rely on the covenants in the Merger Agreement as actual limitations on the respective businesses of Bottomline, Parent and Merger Sub, because the parties may take certain actions that are either expressly permitted in the confidential disclosure letter to the Merger Agreement or as otherwise consented to by the appropriate party, which consent may be given without prior notice to the public. The Merger Agreement is described below, and included as Annex A, only to provide you with information regarding its terms and conditions, and not to provide any other factual information regarding Bottomline, Parent, Merger Sub or their respective businesses. Accordingly, the representations, warranties, covenants and other agreements in the Merger Agreement should not be read alone, and you should read the information provided elsewhere in this document and in our filings with the SEC regarding Bottomline and our business.

Effects of the Merger; Directors and Officers; Certificate of Incorporation; Bylaws

The Merger Agreement provides that, subject to the terms and conditions of the Merger Agreement, and in accordance with the DGCL, at the Effective Time, Merger Sub will be merged with and into Bottomline, the separate corporate existence of Merger Sub will cease, and Bottomline will continue as the Surviving Corporation and as a wholly owned subsidiary of Parent.

Effective as of, and immediately following, the Effective Time, the board of directors of the Surviving Corporation will consist of the directors of Merger Sub immediately prior to the Effective Time, each to hold office in accordance with the certificate of incorporation and bylaws of the Surviving Corporation until the earlier of their death, resignation or removal or until their successors are duly elected and qualified, as the case may be. From and after the Effective Time, the officers of Bottomline immediately prior to the Effective Time will be the officers of the Surviving Corporation, until the earlier of their death, resignation or removal or until

their successors have been duly elected or appointed and qualified, as the case may be. At the Effective Time, the certificate of incorporation of Bottomline as the Surviving Corporation will be amended and restated to be identical to the certificate set forth in Exhibit A to the Merger Agreement until changed or amended in accordance with applicable law and the applicable provisions of such certificate, and the bylaws of the Surviving Corporation, without any further action on the part of Bottomline or Merger Sub, will be the bylaws of Merger Sub in effect immediately prior to the Effective Time (except references to Merger Sub’s name will be replaced by references to “Bottomline Technologies, Inc.”).

Closing and Effective Time

The closing of the transactions contemplated by the Merger Agreement will take place as soon as possible and no later than the second business day following the satisfaction or (to the extent permitted by law) waiver of all conditions to closing of the transactions contemplated by the Merger Agreement (described below under the caption “ —Conditions to the Closing of the Merger”) (other than those conditions that, by their nature, are to be satisfied at the closing of the transactions contemplated by the Merger Agreement) or such other time agreed to in writing by Parent and Bottomline. Concurrently with the closing of the transactions contemplated by the Merger Agreement, the parties will file a certificate of merger relating to the Merger with the Secretary of State for the State of Delaware as provided under the DGCL. The Merger will become effective upon the filing of the certificate of merger, or at such later time as is agreed by the parties and specified in the certificate of merger.

Merger Consideration

Common Stock

At the Effective Time, each outstanding share of common stock (other than shares owned by (1) Parent or Merger Sub; (2) any subsidiary of the Company; and (3) stockholders who are entitled to and who properly exercise appraisal rights under the DGCL) will be converted into the right to receive the Per Share Merger Consideration (which is $57.00 per share, less any applicable withholding taxes) without interest. All shares converted into the right to receive the Per Share Merger Consideration will no longer be outstanding and automatically be cancelled at the Effective Time and the holders of such shares will cease to have any rights thereto, except for the right to receive the Per Share Merger Consideration.

Outstanding Equity Awards

The Merger Agreement provides that Bottomline’s equity awards that are outstanding immediately prior to the Effective Time will be subject to the following treatment at the Effective Time:

Exchange and Payment Procedures

Prior to the Effective Time, Parent will appoint a bank, trust or transfer agent company reasonably acceptable to Bottomline, which institution we refer to as the “paying agent,” to make payments of the Per Share Merger Consideration to stockholders. Immediately prior to the Effective Time, Parent will deposit with the paying agent cash constituting an amount equal to the aggregate Per Share Merger Consideration payable to stockholders (other than any merger consideration in respect of any dissenting shares).

As reasonably promptly as practicable (but no later than the third business day) after the Effective Time, Parent will cause the paying agent to mail to each holder of record of Bottomline common stock (other than Bottomline, its subsidiaries, Parent and Merger Sub) a form of letter of transmittal together with instructions thereto. Upon receipt of (i) in the case of shares of Bottomline common stock represented by a stock certificate, a surrendered certificate or certificates in respect of such shares together with the signed letter of transmittal or (ii) in the case of shares of Bottomline common stock held in book-entry form, the receipt of an “agent’s message” by the paying agent, and in each case, together with such other documents as may be reasonably required by the paying agent, the holder of such shares will be entitled to receive the Per Share Merger Consideration in exchange therefor. The amount of any Per Share Merger Consideration paid to the stockholders may be reduced by any applicable withholding taxes. No interest will be paid or will accrue on the cash payable upon surrender of any stock certificate or shares of stock held in book-entry form.

If any cash deposited with the paying agent remains undistributed to holders of Bottomline common stock one (1) year after the Effective Time, such cash (including any interest received with respect thereto) will be

delivered to Parent or its designee, and any holder of Bottomline common stock who has not complied with the exchange procedures in the Merger Agreement will thereafter look only to the Surviving Corporation as a general unsecured creditor thereof for payment of its claim for the Per Share Merger Consideration, without any interest thereon.

If any stock certificate has been lost, stolen or destroyed, upon the making of an affidavit, in form and substance reasonably acceptable to Parent, of that fact by the person claiming such stock certificate to be lost, stolen or destroyed (and if required by Parent, the posting of such person of a bond, in such reasonable amount as Parent may direct, as indemnity against any claim that may be made against it with respect to such stock certificate), the paying agent will, in exchange for such lost, stolen or destroyed stock certificate, pay the Per Share Merger Consideration deliverable in respect thereof pursuant to the Merger Agreement.

Representations and Warranties

The Merger Agreement contains representations and warranties of Bottomline, Parent and Merger Sub.

Bottomline

Certain of the representations and warranties in the Merger Agreement made by Bottomline are qualified as to “materiality” or “Company Material Adverse Effect.” “Company Material Adverse Effect” means any fact, circumstance, occurrence, effect, change, event or development that, individually or in the aggregate, has or would reasonably be expected to (i) have a material adverse effect on the business, results of operations or condition (financial or otherwise) of Bottomline and its subsidiaries, taken as a whole; or (ii) prevent or materially impair, interfere with, hinder or delay the consummation of the Merger or the other transactions contemplated by the Merger Agreement. The foregoing notwithstanding, none of the following will be taken into account in determining whether such Company Material Adverse Effect has occurred for purposes of clause (i) of the prior sentence:

However, in the case of the exclusions set forth in bullets 1 through 6 immediately above, to the extent any fact, circumstance, occurrence, effect, change, event or development arising from or related to such exclusions materially disproportionately affects Bottomline and its subsidiaries, taken as a whole, relative to other companies of similar size in the industries in which Bottomline and its subsidiaries operate, only the incremental disproportionate effect may be taken into account in determining whether a Company Material Adverse Effect has occurred.

In the Merger Agreement, Bottomline has made customary representations and warranties to Parent and Merger Sub that are subject, in some cases, to specified exceptions and qualifications contained in the Merger Agreement. These representations and warranties relate to, among other things:

Parent and Merger Sub

Certain of the representations and warranties in the Merger Agreement made by Parent and Merger Sub are qualified as to a “Parent Material Adverse Effect.” “Parent Material Adverse Effect” means with respect to Parent or Merger Sub, any fact, circumstance, occurrence, effect, change, event or development that, individually or in the aggregate, would be reasonably expected to prevent or materially impair, interfere with, hinder or delay the consummation of the Merger or the other transactions contemplated by the Merger Agreement.

In the Merger Agreement, Parent and Merger Sub have made customary representations and warranties to Bottomline that are subject, in some cases, to specified exceptions and qualifications contained in the Merger Agreement. These representations and warranties relate to, among other things:

None of the representations and warranties contained in the Merger Agreement survive the consummation of the Merger.

Conduct of Business Pending the Merger

The Merger Agreement provides that, except (1) as set forth in the confidential disclosure letter to the Merger Agreement; (2) as expressly permitted, required or contemplated by the Merger Agreement; (3) as required in order to not be in violation of any applicable law; or (4) with the prior written consent of Parent (which consent may not be unreasonably withheld, conditioned or delayed), during the period of time between the signing of the Merger Agreement and the earlier of the Effective Time and the valid termination of the Merger Agreement, Bottomline will, and will cause each of its subsidiaries to:

In addition, Bottomline has also agreed that, except (1) as set forth in the confidential disclosure letter to the Merger Agreement; (2) as expressly permitted or required by the Merger Agreement; (3) as required in order to not be in violation of any applicable law; or (4) with the prior written consent of Parent (which consent may not be unreasonably withheld, conditioned or delayed), during the period of time between the signing of the Merger Agreement and the earlier of the Effective Time and the valid termination of the Merger Agreement, Bottomline will not, and will not permit any of its subsidiaries to, subject in each case to certain specified exceptions, among other things:

Parent’s and Merger Sub’s Conduct of Business Pending the Merger

Except with respect to governmental approvals, which are addressed separately in the Merger Agreement, the Merger Agreement provides that, except as expressly permitted, contemplated or required by the Merger Agreement, as required by applicable law or with the prior written consent of Bottomline, from the date of the Merger Agreement to the Effective Time, each of Parent and Merger Sub will not, and will cause their respective affiliates to not, take any actions or omit to take any actions that would or would be reasonably expected to impair, interfere with, hinder, delay, or prevent the ability of Parent, Bottomline or Merger Sub to consummate the Merger and the other transactions contemplated by the Merger Agreement in accordance with the terms of the Merger Agreement.

Acquisition Proposals

Under the Merger Agreement, from the date of the Merger Agreement until the earlier of the Effective Time or termination of the Merger Agreement, Bottomline has agreed not to, and to cause its subsidiaries not to (and Bottomline and its subsidiaries will not instruct, authorize or knowingly permit any of their respective representatives to), directly or indirectly, among other things:

From the time that the Merger Agreement is executed until the earlier to occur of the valid termination of this Merger Agreement pursuant to its terms and the Effective Time, Bottomline will not be required to enforce, and will be permitted to waive, any provision of any standstill or confidentiality agreement that prohibits or purports to prohibit a proposal being made to the Board of Directors (or any committee thereof) if, and only if, the Board of Directors (or a committee thereof) determines in good faith (after consultation with its financial advisors and outside legal counsel) that the failure to do so (i) would prohibit the counterparty from making an unsolicited Acquisition Proposal to the Board of Directors in compliance with the Merger Agreement and (ii) would be inconsistent with the Board of Directors’ fiduciary duties under applicable law.

Unless otherwise permitted under the Merger Agreement, the Board of Directors may not, among other things:

Notwithstanding anything to the contrary in the Merger Agreement, at any time following the execution of the Merger Agreement and prior to the time of Bottomline’s receipt of the company stockholder approval, if Bottomline receives an unsolicited written Acquisition Proposal that was not the result of a material breach of the Merger Agreement and the Board of Directors (or a committee thereof) has determined in good faith (after consultation with its financial advisors and outside legal counsel) that such unsolicited Acquisition Proposal either constitutes a Superior Proposal or could reasonably be expected to lead to a Superior Proposal, Bottomline and the Board of Directors (or a committee thereof) may, directly or indirectly through one or more of their representatives, participate or engage in discussions or negotiations with, furnish any non-public information relating to Bottomline or any of its subsidiaries to, or afford access to the business, properties, assets, books, records or other non-public information, or to any personnel, of Bottomline or any of its subsidiaries pursuant to an Acceptable Confidentiality Agreement to any person or its representatives that has made, renewed or delivered to Bottomline an Acquisition Proposal after the date of the Merger Agreement, and otherwise facilitate such Acquisition Proposal or assist such person (and its representatives and financing sources) with such Acquisition Proposal if requested by such person; provided that, subject to applicable law, Bottomline must provide to Parent and Merger Sub any non-public information or data that is provided to any person given such access that was not previously made available (whether prior to or after the execution of the Merger Agreement) to Parent or Merger Sub prior to or substantially concurrently with the time it is provided to such person.

From the time Merger Agreement is executed until the earlier to occur of the valid termination of the Merger Agreement and the Effective Time, Bottomline will as promptly as reasonably practicable (and, in any event, within 48 hours) notify Parent if any Acquisition Proposal or any Inquiries are received by Bottomline or any of its representatives. Such notice must include (i) the identity of the person or group making such Acquisition Proposal or Inquiries; (ii) the material terms and conditions of such offers or proposals; and (iii) if available, copies of any written materials relating thereto provided to Bottomline or its representatives. Thereafter, Bottomline must keep Parent reasonably informed, on a prompt basis, of the status and material change to the terms of any such Acquisition Proposal or inquiries, offers or proposals (including any material amendments thereto) and the status of any related substantive discussions or negotiations. Bottomline must notify Parent that it has entered into an Acceptable Confidentiality Agreement with any person within 24 hours after the execution thereof.

For purposes of this proxy statement and the Merger Agreement:

The Board of Directors’ Recommendation; Company Board Recommendation Change

As described above, and subject to the provisions described below, the Board of Directors has made the recommendation that the holders of shares of Bottomline common stock vote “FOR” the proposal to adopt the Merger Agreement. The Merger Agreement provides that the Board of Directors may not effect a Company Board Recommendation Change except as described below.

The Board of Directors may not (with any action described in the following being referred to as an “Company Board Recommendation Change”):

Prior to the Special Meeting, and notwithstanding the restrictions described above in “ — Acquisition Proposals,” the Board of Directors is permitted in certain circumstances, and subject to Bottomline’s compliance with certain obligations (as summarized below), to (i) make a Company Board Recommendation Change, and (ii) terminate the Merger Agreement and enter into a definitive written agreement providing for a Superior Proposal.

Notwithstanding anything to the contrary in the Merger Agreement, at any time prior to obtaining the company stockholder approval:

Notwithstanding the restrictions described above, the Merger Agreement does not prohibit Bottomline or the Board of Directors (or a committee thereof) from (i) taking and disclosing to Bottomline’s stockholders a position contemplated by Rule 14d-9 or Rule 14e-2(a) promulgated under the Exchange Act (or any similar communication in connection with the making or amendment of a tender offer or exchange offer), (ii) making a customary “stop-look-and-listen” communication to Bottomline’s stockholders pursuant to Rule 14d-9(f) under the Exchange Act (or any similar communication), or (iii) making any legally required disclosure to Bottomline’s stockholders pursuant to applicable securities laws with regard to the transactions contemplated by the Merger Agreement or an Acquisition Proposal; provided that the foregoing will in no way eliminate or modify the effect that such disclosure would otherwise have under the Merger Agreement.

Employee Benefits

For a period of one year immediately following the closing date, or, if earlier, the date of such employee’s termination of employment, Parent will cause the Surviving Corporation or one of its affiliate to provide all

employees of Bottomline who remain employed by the Surviving Corporation or any affiliate of Parent following the Merger, which we refer to as “continuing employees,” (i) at least the same aggregate base salary and target annual cash bonus opportunity provided to such continuing employees immediately prior to the closing date and (ii) other compensation and employee benefits (other than the opportunity to participate in equity-based incentive compensation or other cash- or equity-based long-term incentive compensation opportunities, defined benefit pension, retiree or post-employment welfare or nonqualified deferred compensation) that, are substantially similar in the aggregate to such compensation and benefits provided to such employee immediately prior to the closing date. For a period of one year following the closing date, Parent will cause the Surviving Corporation or one of its affiliates to provide severance benefits to continuing employees who incur a termination of employment during such period that are no less favorable than the severance benefits to which such employee would have been entitled with respect to such termination under the severance policies of Bottomline and its subsidiaries as in effect immediately prior to the date of the Merger Agreement. Parent will cause the Surviving Corporation or one of its affiliates to grant any continuing employee credit for such continuing employees’ service with Bottomline for purposes of eligibility and determination of the level of vacation benefits and severance benefits, but not for purposes of benefit accruals under defined benefit pension plans, under corresponding benefit plans maintained by Parent or the Surviving Corporation in which a continuing employee participates to the same extent and for the same purpose as recognized by Bottomline under the applicable Bottomline employee benefit plan immediately prior to the closing date; provided, however, that such service will not be recognized to the extent that such recognition would result in a duplication of benefits with respect to the same period of service (including with respect to severance benefits to be provided to continuing employees).

Financing

Under the Merger Agreement, Parent represents to Bottomline that:

Parent and Merger Sub further acknowledge and agree that their obligations under the Merger Agreement are not subject to any conditions regarding Parent’s, Merger Sub’s or any other person’s ability to obtain equity or debt financing for the consummation of the transactions contemplated by the Merger Agreement; provided that the foregoing does not limit the express conditions required pursuant to the Merger Agreement in order for Bottomline to enforce Parent’s and Merger Sub’s obligations to cause the Equity Financing to be funded and to consummate the Merger and pursuant to the Equity Commitment Letter in order for Bottomline, as an express third-party beneficiary, to enforce the terms of the Equity Commitment Letter against the Thoma Bravo Fund as if Bottomline were a party thereto.

Financing Cooperation

Bottomline has agreed that prior to the earlier of the closing and the termination of the Merger Agreement, Bottomline will and will cause its applicable subsidiaries to, at Parent’s sole cost and expense, use commercially reasonable efforts to cause the appropriate officers and employees of Bottomline and its applicable subsidiaries to provide such cooperation as is necessary, customary and reasonably requested by Parent solely in connection with Parent’s efforts to obtain the Debt Financing, if any (provided that none of Bottomline, its subsidiaries or any of their respective officers or employees will be obligated to cooperate with a “high-yield” bond financing and such requested cooperation does not unreasonably interfere with the ongoing operations of Bottomline or its subsidiaries). Such cooperation by Bottomline and its subsidiaries may include, at the reasonable request of Parent:

Notwithstanding anything in the Merger Agreement to the contrary, none of Bottomline, its subsidiaries or any officer, employee or representative of any of the foregoing, will be required to:

Bottomline consents to the use of the logos of Bottomline and its subsidiaries by Parent in connection with the Debt Financing; provided, however, that Parent must ensure that such logos are used solely in a manner that is not intended, or that is not reasonably likely, to harm or disparage Bottomline or its reputation or goodwill. Bottomline and each of its subsidiaries will be deemed to be in compliance with this provision, and neither Parent nor any of its affiliates may allege that Bottomline or any of its subsidiaries is or has not been in compliance with this provision, unless the Debt Financing (if any) has not been obtained solely as a result of a deliberate action or omission taken or omitted to be taken by Bottomline in material breach of its obligations under this provision with knowledge of Bottomline that such action or omission would, or would reasonably be expected to, cause such material breach of such obligations.

Parent will, promptly (and in any event within two business days of delivery of documentation evidencing the applicable cost or expense) upon request by Bottomline, reimburse Bottomline for all documented out-of-pocket

costs and expenses (including outside attorneys’ fees and disbursements) incurred by Bottomline, its subsidiaries and their respective representatives in connection with the cooperation contemplated by the Merger Agreement. Parent will indemnify and hold harmless Bottomline, its subsidiaries and their respective representatives from and against any and all losses suffered or incurred by any of them in connection with their compliance with these provisions (other than with respect to any information provided in writing by Bottomline, its subsidiaries or any of their respective representatives expressly for use in connection with the Debt Financing).

All non-public or other confidential information provided by or on behalf of Bottomline to Parent or its affiliates or any of their respective representatives pursuant to these provisions must be kept confidential in accordance with the terms of the confidentiality agreement; provided, however, that Parent will be permitted to disclose information as necessary and consistent with customary practices in connection with the Equity Financing and the Debt Financing subject to customary confidentiality arrangements.

Prior to closing, Bottomline will deliver (or cause to be delivered) to Parent (i) a customary payoff letter sufficient to repay in full Bottomline’s outstanding indebtedness under its existing credit agreement, (ii) duly executed intellectual property rights security interest releases in customary form and substance for recordation in the United States Patent and Trademark Office and (iii) other documents in customary form and substance and solely to the extent necessary to release the liens granted, and guarantees provided, under Bottomline’s existing credit agreement, subject to the occurrence of the closing.

Parent acknowledges and agrees that it will be fully responsible for obtaining the Equity Financing and will take (or cause to be taken) all actions, and do (or cause to be done) all things, necessary, proper or advisable to obtain the Equity Financing pursuant to and in accordance with and subject to the terms and conditions set forth in the Equity Commitment Letter, including taking all actions necessary to (i) comply with the terms of and maintain in effect the Equity Commitment Letter, (ii) satisfy on a timely basis all conditions in such Equity Commitment Letter which can be satisfied by Parent and (iii) consummate the Equity Financing at or prior to the closing subject to the terms and conditions of the Equity Commitment Letter.

Under the Merger Agreement, neither the obtaining of the Equity Financing, any Debt Financing or any alternative financing, nor the completion of any issuance of securities contemplated by the Equity Financing, any Debt Financing or any alternative financing, is a condition to the closing.

Efforts to Close the Merger

Parent and Bottomline have agreed to use, and to cause their respective affiliates to use, their respective reasonable best efforts to reasonably promptly take, or cause to be taken, all actions and to do, or cause to be done, all things necessary, proper or advisable under the Merger Agreement and applicable laws to consummate and make effective as reasonably promptly as practicable after the date of signing of the Merger Agreement and in any event no later than the End Date the transactions contemplated by the Merger Agreement.

Notwithstanding anything to the contrary set forth in the Merger Agreement, in no event will Parent be required to invest any additional capital in Bottomline or any of its affiliates prior to the closing or otherwise take any action or commit to take any action or agree to any condition or restriction that would reasonably be expected to have a material adverse effect on the business, assets, liabilities or operations of Parent or its affiliates, taken as a whole.

Indemnification and Insurance

For a period of six years from the Effective Time, Parent has agreed that all rights to indemnification, advancement of expenses and exculpation from liabilities for acts or omissions occurring at or prior to the Effective Time which were in existence as of the signing of the Merger Agreement in favor of the current and former directors or officers of Bottomline or any of its subsidiaries as provided in their respective governing or

organizational documents and any indemnification or other similar agreements of Bottomline or certain of its subsidiaries, in each case as in effect on the date of the Merger Agreement to continue in full force and effect in accordance with their terms, for a period of no less than six years from and after the Effective Time, and Parent will cause each of Bottomline and its subsidiaries to perform their obligations thereunder. Without limiting the foregoing, from and after the Effective Time and ending on the date that is the sixth anniversary of the closing date, Parent will cause the Surviving Corporation to, and the Surviving Corporation has agreed that it will, indemnify and hold harmless each individual who was as of the date of the Merger Agreement, or who becomes prior to the Effective Time, a director or officer of Bottomline or any of its subsidiaries, or who was as of the date of the Merger, or who thereafter commenced prior to the Effective Time, serving at the request of Bottomline or any of its subsidiaries as a director or officer of another person, against all claims, losses, liabilities, damages, judgements, inquiries, fines and reasonable fees, costs and expenses, including attorneys’ fees and disbursements, incurred in connection with any claim, action, suit or proceeding, whether civil, criminal, administrative or investigative (including with respect to matters existing or occurring at or prior to the Effective Time, including the Merger Agreement and the transactions and actions contemplated thereby), arising out of or pertaining to the fact that such person is or was a director or officer of Bottomline or any of its subsidiaries or is or was serving at the request of Bottomline or any of its subsidiaries as a director or officer of another person, whether asserted or claimed at, prior to or after the Effective Time, to the fullest extent permitted under the governing or organizational documents of Bottomline and its subsidiaries and any indemnification or other similar agreements of Bottomline and any of its subsidiaries. In the event of any such claim, action, suit or proceeding, such person will be entitled to advancement of expenses incurred in the defense of any such claim, action, suit or proceeding from the Surviving Corporation in accordance with the organizational documents of the Surviving Corporation in effect on the date of the Merger Agreement; provided that any person to whom expenses are advanced provides an undertaking, if and only to the extent required by the DGCL or the Surviving Corporation’s certificate of incorporation or bylaws to repay such advances if it is ultimately determined by final adjudication that such person is not entitled to indemnification, and the Surviving Corporation will reasonably cooperate in the defense of any such matter.

For a period of six years from and after the Effective Time, Parent and the Surviving Corporation will either cause to be maintained in effect the current policies of directors’ and officers’ liability insurance maintained by Bottomline or its subsidiaries or provide substitute policies for Bottomline and its subsidiaries and their current and former directors and officers who are currently covered by the directors’ and officers’ insurance coverage currently maintained by Bottomline and its subsidiaries, in either case, of not less than the existing coverage and having other terms not less favorable to the insured persons than the directors’ and officers’ liability insurance coverage currently maintained by Bottomline or its subsidiaries with respect to claims arising from facts or events that occurred on or before the Effective Time (with insurance carriers having at least an “A” rating by A.M. Best with respect to directors’ and officers’ liability insurance), except that in no event shall Parent or the Surviving Corporation be required to pay with respect to any annual policy period more than 350% of the aggregate annual premium most recently paid by Bottomline prior to the date of the Merger Agreement. If the Surviving Corporation is unable to obtain such insurance coverage, it will obtain as much comparable insurance as possible within such six-year period for a premium equal to such maximum amount. In lieu of such insurance, prior to the closing of the Merger, Bottomline may, at its option, purchase a “tail” directors’ and officers’ liability insurance policy for Bottomline and its subsidiaries and the insured persons who are currently covered by the directors’ and officers’ liability insurance coverage currently maintained by Bottomline and its subsidiaries, such tail to provide coverage in an amount not less than the existing coverage and to have other terms not less favorable to the insured persons than the directors’ and officers’ liability insurance coverage currently maintained by Bottomline or its subsidiaries with respect to claims arising from facts or events that occurred at or before the Effective Time; provided that in no event will the cost of any such tail policy exceed the maximum amount described in the preceding sentence. Parent and the Surviving Corporation shall maintain such policies in full force and effect, and continue to honor the obligations thereunder.

Other Covenants

Stockholders Meeting

Bottomline has agreed to duly call, establish a record date for, give notice of, convene and hold a meeting of stockholders as reasonably promptly as practicable after the date of the Merger Agreement following the clearance of this proxy statement by the SEC for the purpose of (i) seeking the approval and adoption of the Merger Agreement by Bottomline’s stockholders and (ii) in accordance with Section 14A of the Exchange Act and the applicable SEC rules issued thereunder, seeking advisory approval of a proposal to Bottomline’s stockholders for a non-binding, advisory vote to approve certain compensation that may become payable by Bottomline to its named executive officers in connection with the completion of the Merger.

Stockholder Litigation

Bottomline will keep Parent reasonably and promptly informed, but only to the extent that doing so would not, in the reasonable judgment of Bottomline’s legal counsel, jeopardize attorney-client privilege, regarding any suit, action or other proceeding commenced or, to the knowledge of Bottomline, threatened against Bottomline or its current or former directors or officers by any stockholder of Bottomline relating to, arising out of or involving the Merger Agreement, the Merger or any of the other transactions contemplated thereby. Bottomline will (a) give Parent the opportunity to participate in the defense, settlement or prosecution of any such litigation and (b) consult with Parent with respect to the defense and settlement of any such litigation and will not compromise or settle any such litigation unless Parent has consented thereto (which consent will not be unreasonably withheld, conditioned or delayed).

Conditions to the Closing of the Merger

The respective obligations of each party to consummate the Merger are subject to the satisfaction or (to the extent permitted by law) waiver by Bottomline and Parent of the following conditions:

In addition, the obligations of Parent and Merger Sub to consummate the Merger are subject to the satisfaction or waiver by Parent of each of the following additional conditions:

In addition, the obligation of Bottomline to consummate the Merger is subject to the satisfaction or waiver by Bottomline of each of the following additional conditions:

Termination of the Merger Agreement

The Merger Agreement may be terminated at any time prior to the Effective Time, whether before or after the adoption of the Merger Agreement by Bottomline’s stockholders, in the following ways:

Written notice of termination of the Merger Agreement by either Bottomline or the Parent pursuant to the termination rights above must be given to the other party or parties specifying the provisions of the Merger Agreement pursuant to which such termination is made, and, upon the valid termination of the Merger Agreement pursuant to its terms, the Merger Agreement will become void and have no effect without any further liability or obligation on the part of any party thereto. However, certain provisions of the Merger Agreement relating to certain confidentiality obligations, certain indemnification and reimbursement obligations, the effect of termination of the Merger Agreement, termination fees, expenses, and certain general provisions will survive any termination of the Merger Agreement. Termination will not relieve any party of liability and each party will remain liable for certain losses resulting from any intentional common law fraud or any willful and material breach of the Merger Agreement prior to or in connection with such termination. Parent and Merger Sub acknowledge and agree that, without in any way limiting Bottomline’s rights under the Merger Agreement but subject to the parent liability limitation (in the amount equal to $195,000,000), recoverable damages of Bottomline under the Merger Agreement are not limited to reimbursement of expenses or out-of-pocket costs, and include the benefit of the bargain lost by the equityholders of Bottomline (including “lost premium”), taking into consideration relevant matters, including the total amount payable to Bottomline’s equityholders under the Merger Agreement and the time value of money, which in each case will be deemed in such event to be damages of Bottomline and will be recoverable by Bottomline on behalf of its equityholders.

Termination Fees and Expense Reimbursement

If the Merger Agreement is terminated in specified circumstances, Bottomline may be required to pay a termination fee. Parent would be entitled to receive a termination fee equal to $78,000,000 from Bottomline under the following circumstances:

If the Merger Agreement is terminated because (i) Bottomline’s stockholders fail to approve the proposal to approve and adopt the Merger Agreement at the Special Meeting or (ii) Bottomline has breached its representations, warranties, covenants or other agreements in the Merger Agreement in certain circumstances and has failed to cure such breach within the requisite period, in each case, under circumstances in which the termination fee is not then payable (but could become payable in the future), and prior to the time of such termination, Parent and Merger Sub were not in material breach of their representations, warranties, covenants or agreements under the Merger Agreement, then Bottomline would be required, no later than two business days after the date of such termination, to reimburse Parent up to $5,000,000 in respect of Parent’s reasonable and documented out-of-pocket fees and expenses incurred by Parent and its affiliates in connection with the Merger Agreement and the transactions contemplated thereby (with such reimbursement deducted from the termination fee, should it not be payable at the time of such termination but subsequently become payable).

Specific Performance; Monetary Damages

Prior to the valid termination of the Merger Agreement, Parent and Merger Sub are entitled to seek and obtain an injunction, specific performance and other equitable relief to prevent breaches of the Merger Agreement by Bottomline in the courts described in the Merger Agreement and to enforce specifically the terms and provisions of the Merger Agreement, including Bottomline’s obligation to consummate the Merger.

Prior to the valid termination of the Merger Agreement and other than as it relates to the right to cause the Equity Financing to be funded and to consummate the Merger, Bottomline will be entitled to seek and obtain an injunction, specific performance and other equitable relief to prevent breaches of the Merger Agreement by Parent and Merger Sub in the courts described in the Merger Agreement and to enforce specifically the terms and provisions of the Merger Agreement.

Prior to a valid termination of the Merger Agreement, Bottomline will be entitled to seek and obtain an injunction, specific performance and other equitable relief to enforce Parent’s and Merger Sub’s obligations to

cause the Equity Financing to be funded and to consummate the Merger only in the event that each of the following conditions has been satisfied:

In no event will Bottomline be entitled to seek the remedy of specific performance to cause the Equity Financing to be funded and to cause the consummation of the Merger other than solely under the specific circumstances and as specifically set forth in the Merger Agreement.

Without limiting Bottomline’s other rights to reimbursement and indemnification set forth in the Merger Agreement, other than in the case of intentional common law fraud or willful and material breach as set forth in the Merger Agreement, in no event will Bottomline, its subsidiaries, and their related parties have the right to seek or obtain money damages or expense reimbursement (whether at law or in equity, in contract, in tort or otherwise) from Parent, Merger Sub, the Thoma Bravo Fund and their related parties in connection with the transactions contemplated by the Merger Agreement. Under no circumstances will the collective monetary damages payable by Parent, Merger Sub, the Thoma Bravo Fund or any of their affiliates for breaches under the Merger Agreement exceed $195,000,000.

Fees and Expenses

Except in specified circumstances, whether or not the Merger is completed, Bottomline, on the one hand, and Parent and Merger Sub, on the other hand, are each responsible for all of their respective costs and expenses incurred in connection with the Merger and the other transactions contemplated by the Merger Agreement.

Amendment

The Merger Agreement may be amended in writing by the parties to the Merger Agreement at any time before or after adoption of the Merger Agreement by Bottomline’s stockholders. However, after adoption of the Merger Agreement by Bottomline’s stockholders, (i) no amendment that requires further approval by such stockholders by law may be made without such approval and (ii) except as provided above, no amendment will be submitted to be approved by Bottomline’s stockholders unless required by law.

Governing Law

The Merger Agreement is governed by Delaware law.

The Voting Agreement

Parent and Bottomline have entered into the Voting Agreement with the Supporting Shareholders, which collectively hold approximately 4% of the outstanding shares of Bottomline’s common stock.stock, as of the date of the Voting Agreement. A copy of the Voting Agreement is attached as Annex D and is incorporated herein by reference. Under the Voting Agreement the Supporting Shareholders agree, among other things, during the term of the Voting Agreement, to vote their shares of common stock (i) in favor of the adoption of the Merger Agreement and the approval of the Merger and the other transactions contemplated thereby and (ii) against any alternative acquisition proposal, and not to, directly or indirectly, sell, transfer, exchange or otherwise dispose of their shares, subject to certain limited exceptions.

The Voting Agreement will terminate upon the earlier to occur of (a) the time that the stockholder approval has been obtained, (b) the Effective Time, (c) such date and time as the Merger Agreement is validly terminated in accordance with its terms and (d) any amendment of any term or provision of the original Merger Agreement that reduces the Per Share Merger Consideration or changes the form of consideration payable to the Supporting Shareholders pursuant to the Merger Agreement, without such Supporting Shareholder’s prior consent.

MARKET PRICES AND DIVIDEND DATA

Our common stock is listed on NASDAQ under the symbol “EPAY”. As of [●],the Record Date, there were [●]44,977,553 shares of common stock outstanding, held by approximately [●]83 stockholders of record. We have never declared or paid any cash dividends on our common stock.

The following table presents the high and low intra-day sale prices of our common stock on NASDAQ during the fiscal quarters indicated:

On [●],February 1, 2022, the latest practicable trading day before the printing of this proxy statement, the closing price for our common stock on NASDAQ was $[●]$56.39 per share. You are encouraged to obtain current market quotations for our common stock.

Following the Merger, there will be no further market for our common stock and it will be delisted from NASDAQ and deregistered under the Exchange Act. As a result, following the Merger we will no longer file periodic reports with the SEC.

SECURITY OWNERSHIP OF CERTAIN BENEFICIAL OWNERS AND MANAGEMENT

The following table sets forth information, as of December 14, 2021,January 24, 2022, regarding the beneficial ownership of shares of our common stock by (a) each person or entity known by us to own beneficially more than 5% of the outstanding shares of our common stock, (b) each of the “named executive officers,” (c) each current director of Bottomline and (d) all executive officers and current directors of Bottomline as a group. The address of each of our directors and named executive officers is c/o Bottomline Technologies, Inc., 325 Corporate Drive, Portsmouth, New Hampshire 03801.

Beneficial ownership is determined in accordance with the rules of the Securities and Exchange Commission, which we sometimes refer to as the SEC, and generally includes voting power and/or investment power with respect to securities. As of [December 14, 2021]January 24, 2022 there were [44,960,126]44,980,651 shares of our common stock outstanding. Shares of common stock subject to options currently exercisable or exercisable within 60 days of [December 14, 2021]January 24, 2022 are deemed outstanding for purposes of computing the percentage beneficially owned by the person or entity holding the options, but are not deemed outstanding for purposes of computing the percentage beneficially owned by any other person or entity. All unvested time-based and performance-based restricted stock awards are included in each holder’s beneficial ownership as holders are entitled to voting rights upon issuance of the restricted stock awards. Except as indicated by footnote, we believe that the persons and entities named in this table, based on information provided by them, have sole voting and investment power with respect to the shares of common stock indicated.

FUTURE STOCKHOLDER PROPOSALS

If the Merger is completed, we will have no public stockholders and there will be no public participation in any future meetings of stockholders of Bottomline. However, if the Merger is not completed, stockholders will continue to be entitled to attend and participate in stockholder meetings.

Bottomline will hold an annual meeting in 2022 only if the Merger has not already been completed.

Stockholders interested in submitting a proposal (other than the nomination of directors) for inclusion in the proxy materials to be distributed by us for the 2022 annual meeting of stockholders, if held, may do so by following the procedures prescribed in Rule 14a-8 of the Exchange Act. Any proposal that a stockholder intends to present at the 2022 annual meeting of stockholders must be submitted to our principal executive offices at 325 Corporate Drive, Portsmouth, New Hampshire 03801, Attention: Corporate Secretary, no later than June 23, 2022 in order to be considered for inclusion in the proxy statement and proxy card relating to the 2022 annual meeting of stockholders. However, if the date of our 2022 annual meeting is prior to October 19, 2022 or after December 18, 2022, the deadline is 10 business days before we begin to print and mail our proxy materials for the 2022 annual meeting.

If a stockholder wishes to present a proposal at the 2022 annual meeting but has not complied with the requirements for inclusion of the proposal in our proxy materials pursuant to Rule 14a-8 under the Exchange Act, the stockholder must also give notice of the proposal to our corporate secretary at our principal executive offices. Our second amended and restated by-laws require that we be given advance written notice of stockholder nominations regarding election to our Board of Directors and certain other matters which stockholders wish to present for action at an annual meeting of stockholders (other than matters included in our proxy statement discussed above). We must receive this notice at least 60 days, but not more than 90 days, prior to the date of the 2022 annual meeting, which is expected to be November 17, 2022; provided that if less than 70 days’ notice or prior public disclosure of the date of the meeting is given to stockholders, such notice must instead be received no later than the tenth day following the date on which the notice of the meeting was mailed or such public disclosure was made, whichever occurs first. Our bylaws also specify requirements relating to the content of the notice which stockholders must provide, including for stockholder nominations for director, in order for such proposals or nominations to be properly presented at a stockholder meeting.

WHERE YOU CAN FIND MORE INFORMATION

The SEC allows us to “incorporate by reference” information into this proxy statement, which means that we can disclose important information to you by referring you to other documents filed separately with the SEC. The information incorporated by reference is deemed to be part of this proxy statement, except for any information superseded by information in this proxy statement or incorporated by reference subsequent to the date of this proxy statement. This proxy statement incorporates by reference the documents set forth below that we have previously filed with the SEC. These documents contain important information about us and our financial condition and are incorporated by reference into this proxy statement.

The following Bottomline filings with the SEC are incorporated by reference:

We also incorporate by reference into this proxy statement additional documents that we may file with the SEC between the date of this proxy statement and the earlier of the date of the Special Meeting or the termination of the Merger Agreement. These documents include periodic reports, such as Annual Reports on Form 10-K and Quarterly Reports on Form 10-Q, as well as Current Reports on Form 8-K and proxy soliciting materials. The information provided on our website is not part of this proxy statement, and therefore is not incorporated by reference herein.

Information furnished under Item 2.02 or Item 7.01 of any Current Report on Form 8-K, including related exhibits, is not and will not be incorporated by reference into this proxy statement.

We file annual, quarterly and current reports, proxy statements and other information with the SEC under the Exchange Act. The SEC maintains a website that contains reports, proxy statements and other information that we file electronically with the SEC. The address of that website is www.sec.gov. If you would like to request documents from us, please do so as soon as possible, to receive them before the Special Meeting. Please note that all of our documents that we file with the SEC are also promptly available through the Investor Relations section of our website, www.investors.bottomline.com.www.investors.bottomline.com. The information included on our website is not incorporated by reference into this proxy statement.

You may obtain any of the documents we file with the SEC, without charge, by requesting them in writing or by telephone from us at the following address:

Bottomline Technologies, Inc.

Attn: Corporate Secretary

325 Corporate Drive

Portsmouth, New Hampshire 03801

(603) 436-0700

If you have any questions concerning the Merger, the Special Meeting or this proxy statement, would like additional copies of this proxy statement or need help voting your shares of common stock, please contact our Proxy Solicitor:

Innisfree M&A Incorporated

Stockholders May Call Toll-Free: (877) 687-1865

Banks & Brokers May Call Collect: (212) 750-5833

MISCELLANEOUS

Bottomline has supplied all information relating to Bottomline, and Parent has supplied, and Bottomline has not independently verified, all of the information relating to Parent and Merger Sub contained in this proxy statement.

You should rely only on the information contained in this proxy statement, the annexes to this proxy statement and the documents that we incorporate by reference in this proxy statement in voting on the Merger. We have not authorized anyone to provide you with information that is different from what is contained in this proxy statement. This proxy statement is dated [●],February 2, 2022. You should not assume that the information contained in this proxy statement is accurate as of any date other than that date (or as of an earlier date if so indicated in this proxy statement), and the mailing of this proxy statement to stockholders does not create any implication to the contrary. This proxy statement does not constitute a solicitation of a proxy in any jurisdiction where, or to or from any person to whom, it is unlawful to make a proxy solicitation.

Annex A

EXECUTION VERSION

AGREEMENT AND PLAN OF MERGER

Dated as of DECEMBER 16, 2021

among

BOTTOMLINE TECHNOLOGIES, INC.

PROJECT RB PARENT, LLC

and

PROJECT RB MERGER SUB, INC.

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