UNITED STATES

SECURITIES AND EXCHANGE COMMISSION

Washington, D.C. 20549

SCHEDULE 14A

Proxy Statement Pursuant to Section 14(a) of the

Securities Exchange Act of 1934

(Amendment No.     )

Filed by the Registrant  ☒                             Filed by a Party other than the Registrant  ☐

Check the appropriate box:

PCSB FINANCIAL CORPORATION

(Name of Registrant as Specified In Its Charter)

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

Payment of Filing Fee (Check the appropriate box):

September 10, 201924, 2020

Dear Fellow Stockholder:

You are cordially invited to attend the annual meeting of stockholders of PCSB Financial Corporation. The meeting will be held at our executive offices/headquarters at 2651 Strang Blvd., Suite 100, Yorktown Heights, New York on Wednesday, October 23, 201928, 2020 at 11:00 a.m., local time.

It is important that your shares are represented at the annual meeting, whether or not you attend the meeting in person and regardless of the number of shares you own. To make sure your shares are represented, we urge you to vote by promptly completing and mailing the enclosed proxy card or by voting via the Internet or by telephone. Internet and telephone voting instructions appear on the enclosed proxy card. If you attend the annual meeting, you may vote in person even if you have previously mailed a proxy card or voted via the Internet or by telephone.

We look forward to seeing you.

Sincerely,

Special Notice Regarding In-Person Attendance at Annual Meeting – In light of the ongoing health risks relating to the COVID-19 pandemic and to best protect the health and welfare of our employees, stockholders and community, we urge that stockholders DO NOT ATTEND the Annual Meeting in person this year. Stockholders are nevertheless urged to vote their proxies by mail or by voting via the Internet or by telephone today.

PCSB FINANCIAL CORPORATION

2651 Strang Blvd., Suite 100

Yorktown Heights, NY 10598

(914)248-7272

NOTICE OF 20192020 ANNUAL MEETING OF STOCKHOLDERS

Yorktown Heights, New York

September 10, 201924, 2020

Special Notice Regarding In-Person Attendance at Annual Meeting – In light of the ongoing health risks relating to the COVID-19 pandemic and to best protect the health and welfare of our employees, stockholders and community, we urge that stockholders DO NOT ATTEND the Annual Meeting in person this year. Stockholders are nevertheless urged to vote their proxies by mail or by voting via the Internet or telephone today.

PCSB FINANCIAL CORPORATION

PROXY STATEMENT

FOR

20192020 ANNUAL MEETING OF STOCKHOLDERS

GENERAL INFORMATION

PCSB Financial Corporation is providing this proxy statement to you in connection with the solicitation of proxies by its Board of Directors for use only at the 20192020 annual meeting of stockholders and at any adjournment or postponement of the meeting. In this proxy statement, we may refer to PCSB Financial Corporation as “PCSB Financial,” the “Company,” “we,” “our” or “us.”

We are holding the 20192020 annual meeting of stockholders at our executive offices/headquarters located at 2651 Strang Blvd., Suite 100, Yorktown Heights, New York on Wednesday, October 23, 201928, 2020 at 11:00 a.m., local time.

We intend to provide access tomail this proxy statement and a proxy card to stockholders of record beginning on or about September 10, 2019.24, 2020.

SPECIAL NOTICE REGARDING IN-PERSON ATTENDANCE AT ANNUAL MEETING

Given the ongoing health risks relating to the COVID-19 coronavirus pandemic and the evolving public health measures being instituted by public officials, and to best protect the health and welfare of our employees, stockholders and community, we urge that stockholders DO NOT ATTEND the Annual Meeting in person this year. Stockholders are nevertheless urged to vote their proxies by mail or by voting via the Internet or by telephone. See “Information About Voting – Voting by Proxy” below.

IMPORTANT NOTICE REGARDING THE AVAILABILITY OF PROXY MATERIALS

FOR THE STOCKHOLDERS’ MEETING TO BE HELD ON OCTOBER 23, 201928, 2020

This proxy statement and the Company’s Annual Report on Form10-K, as filed with the Securities and Exchange Commission, are available athttp://astproxyportal.com/ast/21339.

INFORMATION ABOUT VOTING

Who Can Vote

You are entitled to vote your shares of Company common stock that you owned as of the close of business on August 23, 2019.21, 2020. As of the close of business on that date, 17,715,13916,898,137 shares of Company common stock were outstanding. Each share of common stock has one vote.

The Company’s Articles of Incorporation provide that record holders of the Company’s common stock who beneficially own, either directly or indirectly, more than 10% of the Company’s outstanding shares are not entitled to any vote with respect to those shares held above the 10% limit.

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Ownership of Shares; Attending the Meeting

You may own shares of Company common stock in one or more of the following ways:

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In the election of directors, votes that are withheld and brokernon-votes will have no effect on the outcome of the election.

In counting votes on the proposals to ratify the appointment of the independent registered public accounting firm, abstentions and brokernon-votes will have no effect on the outcome of the vote.

Effect of Not Casting Your Vote

If you hold your shares in street name, you must cast your vote if you want it to count in the voting on Item 1 (Election of Directors). Current regulations prohibit your bank or broker from voting

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submission are set forth on the voting instruction cards. Under the terms of the ESOP, all allocated shares of Company common stock held by the ESOP are voted by the ESOP trustee, as directed by plan participants. The ESOP trustee generally votes all unallocated shares of Company common stock held by the ESOP and allocated shares for which no timely voting instructions are received in the same proportion as shares for which the ESOP trustee has received timely voting instructions, subject to the exercise of its fiduciary duties. Under the terms of the 401(k) Plan a participant may direct the trustee how to vote the shares of Company common stock credited to the Participant under the plan. The Company will direct the 401(k) Plan trustee how to vote the shares of Company common stock for which timely voting instructions are not received.The deadline for returning voting instructions is October 16, 2019.21, 2020.

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Board Leadership Structure and Board’s Role in Risk Oversight

The Board of Directors currently combines the offices of Chairman of the Board and Chief Executive Officer, but couples it with the designation of a lead independent director to strengthen the Company’s governance structure. The Board of Directors believes this structure provides an efficient and effective leadership model for the Company. Combining the offices of Chairman of the Board and Chief Executive Officer fosters clear accountability, effective decision-making, alignment on corporate strategy, and a clear and direct channel of communication between senior management and the full Board of Directors. Vice Chairman Richard F. Weiss serves as the lead independent director. The responsibilities of the lead independent director include leading all meetings of independent directors. To assure effective independent oversight, the Board of Directors has adopted various governance practices, including holding executive sessions of the independent directors at least twice a year or more often as needed.

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Audit Committee

The Audit Committee is responsible for providing oversight relating to our consolidated financial statements and financial reporting process, systems of internal accounting and financial controls, internal audit function, annual independent audit and the compliance and ethics programs established by management and the Board of Directors. The Audit Committee is also responsible for engaging the Company’s independent registered public accounting firm and monitoring its conduct and independence. The Board of Directors has designated Richard F. Weiss and Matthew G. McCrosson as “audit committee financial experts” as that term is defined by the rules and regulations of the Securities and Exchange Commission.

Compensation Committee

The Compensation Committee approves the compensation objectives for the Company and PCSB Bank, establishes the compensation for the Company’s and PCSB Bank’s executive management, and conducts the performance review of the Chairman, President and Chief Executive Officer. The Compensation Committee reviews all components of compensation, including salaries, cash incentive plans, long-term incentive plans and various employee benefit matters. Decisions by the Compensation Committee with respect to the compensation of executive officers are approved by the full Board of Directors.

Nominating/Corporate Governance Committee

The Nominating/Corporate Governance Committee assists the Board of Directors: (i) to identify individuals qualified to become Board members, consistent with criteria approved by the Board; (ii) to recommend the director nominees for the next annual meeting; (iii) to implement policies and practices relating to corporate governance, including implementation of and monitoring adherence to corporate governance guidelines; (iv) to lead the Board in its annual review of the Board’s performance; and (v) to recommend director nominees for each committee.

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Minimum Qualifications for Director Nominees.The Nominating/Corporate Governance Committee has adopted a set of criteria that it considers when it selects individuals to be nominated for election to the Board of Directors. A candidate must meet the eligibility requirements set forth in the Company’s Bylaws, which include a residency requirement and a requirement that the candidate have not have been subject to certain criminal or regulatory actions. A candidate also must meet any qualification requirements set forth in any Board or committee governing documents.

If a candidate is deemed eligible for election to the Board of Directors, the Nominating/Corporate Governance Committee will then evaluate the following criteria in selecting nominees:

The Nominating/Corporate Governance Committee also will consider any other factors it deems relevant, including diversity, competition, size of the Board of Directors, and regulatory disclosure obligations.

With respect to nominating an existing director forre-election to the Board of Directors, the Nominating/Corporate Governance Committee will consider and review an existing director’s attendance and performance at meetings of the Board of Directors and meetings of committees on which he or she serves; length of service; the experience, skills and contributions that he or she brings to the Board of Directors; and independence.

Director Nomination Process.The process that the Nominating/Corporate Governance Committee follows to identify and evaluate individuals to be nominated for election to the Board of Directors is as follows:

For purposes of identifying director nominees, the Nominating/Corporate Governance Committee relies on personal contacts of its committee members and other members of the Board of Directors, as well as its knowledge of members of the communities served by PCSB Bank. The Nominating/Corporate Governance Committee will also consider director candidates recommended by stockholders according to the policy and procedures set forth below. The Nominating/Corporate Governance Committee has not used the services of an independent search firm to identify nominees.

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In evaluating potential nominees, the Nominating/Corporate Governance Committee determines whether the candidate is eligible and qualified for service on the Board of Directors by evaluating the candidate under the criteria set forth above. If such individual fulfills these criteria, the Nominating/ Corporate Governance Committee will conduct a check of the individual’s background and interview the candidate to further assess the qualities of the prospective nominee and the contributions he or she would make to the Board of Directors.

Considerations of Recommendations by Stockholders.The policy of the Nominating/Corporate Governance Committee is to consider director candidates recommended by stockholders who appear to be qualified to serve as a director. The Nominating/Corporate Governance Committee may choose not to consider an unsolicited recommendation if no vacancy exists on the Board of Directors and the Nominating/Corporate Governance Committee does not perceive a need to increase the size of the Board of Directors. To avoid the unnecessary use of the Nominating/Corporate Governance Committee’s resources, the Nominating/ Corporate Governance Committee will consider only those director candidates recommended in accordance with the procedures set forth below.

Procedures to be Followed by Stockholders. To submit a recommendation of a director candidate to the Nominating/Corporate Governance Committee, a stockholder should submit the following information in writing, addressed to the Corporate Secretary, at the main office of the Company:

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For a director candidate to be considered for nomination at the Company’s annual meeting of stockholders, the recommendation must be received by the Nominating/Corporate Governance Committee at least 60 days before the date the Company’s proxy statement was released to stockholders in connection with the previous year’s annual meeting, advanced by one year.

Board and Committee Meetings

During the fiscal year ended June 30, 2019,2020, the Company’s Board of Directors held 12 meetings and PCSB Bank’s Board of the Directors held 1213 meetings. No director attended fewer than 75% of the total meetings of the Company’s Board of Directors or of PCSB Bank’s Board of Directors and the respective committees on which such director served during fiscal 2019.2020.

Director Attendance at Annual Meetings of Stockholders

The Board of Directors encourages each director to attend the annual meeting of stockholders. All directors then serving attended the 20182019 annual meeting of stockholders.

Code of Ethics and Business Conduct

The Company has adopted codes of ethics and business conduct which apply to all of the Company’s and PCSB Bank’s directors, officers and employees. They are available on the Investor Relations portion of PCSB Bank’s website (www.pcsb.com).

REPORT OF THE AUDIT COMMITTEE

The Company’s management is responsible for the Company’s internal controls and financial reporting process. The Company’s independent registered public accounting firm is responsible for performing an independent audit of the Company’s consolidated financial statements and issuing an opinion on the conformity of those financial statements with generally accepted accounting principles in the United States of America (“GAAP”). The Audit Committee oversees the Company’s internal controls and financial reporting process on behalf of the Board of Directors.

In this context, the Audit Committee has met and held discussions with management and the independent registered public accounting firm. Management represented to the Audit Committee that the Company’s consolidated financial statements were prepared in accordance with GAAP and the Audit Committee has reviewed and discussed the consolidated financial statements with management and the independent registered public accounting firm. The Audit Committee discussed with the independent registered public accounting firm matters required to be discussed by Public Company Accounting Oversight Board (the “PCAOB”) Auditing Standard No. 1301, which include matters related to the conduct of the audit of the Company’s consolidated financial statements.

In addition, the Audit Committee has received the written disclosures and the letter from the independent registered public accounting firm, required by the applicable requirements of the PCAOB regarding the independent registered public accounting firm’s communications with the Audit Committee concerning independence, and has discussed with the independent registered public accounting firm the firm’s independence from the Company and its management. In concluding that the registered public accounting firm is independent, the Audit Committee considered, among other factors, whether thenon-audit services provided by the firm were compatible with its independence.

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The Audit Committee discussed with the Company’s independent registered public accounting firm the overall scope and plans for their audit. The Audit Committee meets with the independent registered public accounting firm, with and without management present, to discuss the results of their examination, their evaluation of the Company’s internal controls, and the overall quality of the Company’s financial reporting.

In performing all these functions, the Audit Committee acts only in an oversight capacity. In its oversight role, the Audit Committee relies on the work and assurances of the Company’s management, which has the primary responsibility for financial statements and reports, and of the independent registered public accounting firm who, in its report, expresses an opinion on the conformity of the Company’s consolidated financial statements to GAAP. The Audit Committee’s oversight does not provide it with an independent basis to determine that management has maintained appropriate accounting and financial reporting principles or policies, or appropriate internal controls and procedures designed to assure compliance with accounting standards and applicable laws and regulations. Furthermore, the Audit Committee’s considerations and discussions with management and the independent registered public accounting firm do not assure that the Company’s consolidated financial statements are presented in accordance with GAAP, that the audit of the Company’s consolidated financial statements has been carried out in accordance with GAAP or that the Company’s independent registered public accounting firm is “independent.”

In reliance on the reviews and discussions referred to above, the Audit Committee has recommended to the Board of Directors, and the Board of Directors has approved, that the audited consolidated financial statements be included in the Company’s Annual Report on Form10-K for the fiscal year ended June 30, 20192020 for filing with the Securities and Exchange Commission. The Audit Committee also has approved, subject to stockholder ratification, the selection of the Company’s independent registered public accounting firm for the fiscal year ending June 30, 2020.2021.

Audit Committee of the Board of Directors

of

PCSB Financial Corporation

Richard F. Weiss, Chairman

Kevin B. Dwyer

Willard I. Hill, Jr.

Jeffrey D. Kellogg

Matthew G. McCrosson

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DIRECTOR COMPENSATION

The following table sets forth for the fiscal year ended June 30, 2019,2020, certain information as to the total remuneration we paid our directors, other than Mr. Roberto who, as Chairman, President and Chief Executive Officer, receives no additional compensation for service as a director.

Director Fee Deferral Plan.PCSB Bank maintains an Amended and Restated Director Fee Deferral Plan fornon-employee directors. It is anon-qualified deferred compensation plan subject to the requirements of Section 409A of the Internal Revenue Code of 1986, as amended (the “Code”). A participant in the plan is eligible to defer a fixed percentage of the annual and periodic fees the participant would be entitled to receive by completing an election form and submitting it to PCSB Bank before initial participation, and thereafter, if desired, before the beginning of each plan year. The plan was amended in fiscal year 2018 to permit directors aone-time opportunity to invest a portion of their account balance as of the amendment date in Company common stock and to elect to defer all or a portion of their future deferrals towards the purchase of Company common stock in the plan. As of the last day of each plan

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Director Supplemental Life Insurance Plan. PCSB Bank has adopted a Director Supplemental Life Insurance Plan fornon-employee directors. Eligible directors participating in the plan are Dr. Gordon and Messrs. Kellogg, McCrosson, Cuddy, Lusardi, Thimm, Dwyer, and Weiss.

The Director Supplemental Insurance Plan provides for a death benefit to the beneficiaries if the director was in service with PCSB Bank at the time of his death. During a director’s period of coverage, the director is entitled to designate the beneficiary of his death benefit under the plan. The death benefit will be the lesser of (i) $100,000 or (ii) the net death benefit. For these purposes, the “net death benefit” is defined as the net amount at risk under the policy or policies, i.e., the difference between the cash surrender value of the policy and the total proceeds payable under the policy at the death of the insured as of a given date. PCSB Bank is the sole owner of the policies covering the directors and has entered into split dollar endorsements with each director endorsing the applicable amount of death benefit to the director’s beneficiaries in the event of the director’s death. Participation in the plan terminates if: (i) the director’s service with PCSB Bank is terminated for reasons other than death or (ii) the plan is terminated.

Death Benefit Only Plan. Messrs. Hill and Weber participate in a separate Death Benefit Only Plan with PCSB Bank and do not participate in the Director Supplemental Life Insurance Plan. Under the Death Benefit Only Plan, if Messrs. Hill or Weber diespre-retirement, histheir respective beneficiary is entitled to a death benefit equal to $153,850. The death benefit will be paid to their respective beneficiary in a single lump sum within 90 days following histheir death. Messrs. Hill’s and Weber’s participation will terminate if they terminate service as a director or if the plan is terminated. During their service, Messrs. Hill and Weber are entitled to designate their respective beneficiary or to substitute another beneficiary upon written notice to PCSB Bank.

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The following table sets forth, as of August 23, 2019,21, 2020, certain information as to the shares of the Company’s common stock beneficially owned by:

For purposes of this table, a person is deemed to be the beneficial owner of any shares of common stock over which he or she has, or shares, directly or indirectly, voting or investment power or as to which he or she has the right to acquire beneficial ownership at any time within 60 days after August 23, 2019.21, 2020. None of the named individuals has pledged any of his or her shares as collateral for a loan.

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Board Nominees for Terms Expiring in 2022

Joseph D. Roberto, age 66 and a director since 2012, has served as President and Chief Executive Officer of PCSB Bank since January 2012 and as its Chairman of the Board since January 2012 and has served as President, Chief Executive Officer and Chairman of the Board of the Company since its inception in 2017. He served as Chief Financial Officer of PCSB Bank from October 2005 to December 2011. His banking career spans more than 40 years serving in various financial management and executive positions for other financial institutions. Before joining PCSB Bank, he began his career at Yonkers Savings and Loan Association and served as Chief Financial Officer for both Yonkers Financial Corporation and Yonkers Savings and Loan Association, a public community bank, from 1996 to 2002. In 2004 and 2005 he served as Executive Vice President and Chief Financial Officer of Empire State Bank, a public commercial bank.

Mr. Roberto is actively involved in various organizations in both Putnam and Westchester Counties, currently serving on the boards of the Putnam Economic Development Corporation, the Putnam Hospital Center Foundation and the Westchester County Association. He is also actively involved with the American Heart Association and its Putnam Heart Walk, leading PCSB Bank’s efforts in fund raising and heart healthy awareness. Mr. Roberto has been recognized for his leadership and community involvement by many organizations including the NAACP Mount Vernon, NY Branch, the Boys and Girls Club of Mt. Vernon, NY, St. Christopher’s Inn, Garrison NY, and Sunrise Association, Pearl River, NY.

Mr. Roberto’s extensive knowledge of the banking industry and strong leadership skills provide the Board of Directors with invaluable insight and guidance into the business and regulatory requirements of today’s banking environment.

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Dr. Marsha Gordon, age 6465 and a director since 2018, has served as President and Chief Executive Officer of the Business Council of Westchester (“BCW”), a leading business organization in Westchester County, New York, since 2001. As leader of the County’scounty’s largest and most influential business organization, Dr. Gordon brings more than 25 years of community, commerce and leadership to the BCW. A sought-after speaker, panelist and media expert, Dr. Gordon is widely considered to be an authority on the business climate in Westchester and is regularly the“go-to” person on legislative and regulatory issues throughout the Hudson Valley.

Governor Cuomo appointed Dr. Gordon to the executive committee of theMid-Hudson Regional Economic Development Council, resulting in 300+ million of state dollars invested in the region; in 2014 alone $92.8 million returned to the Hudson Valley (the largest award).

Dr. Gordon serves on several Boards including the Business Council of New York State, the Westchester-Putnam Workforce Investment Board and Yonkers STRIVE.Vice President for Membership of the Board or Business Council of New York State. She has been recognized for her leadership by many organizations including the New York Association for Reliable Energy, the YWCA Salute to Women and Racial Justice, and the Food Bank of Westchester. She was also named Most Influential Businessperson by Westchester Magazine.

Before her position with the BCW, Dr. Gordon served as President and Chief Executive Officer of MetroPool, anot-for-profit organization that promotes alternative transportation options in Fairfield County and the Hudson Valley. From 1991 to 1999 she led the 1000-member Greater Southern Dutchess Chamber of Commerce, where she attracted a minor league baseball team to the region.

Dr. Gordon has a BA from Brooklyn College, an MBA from Marist College and a Doctorate in Business Administration from Pace University.

Dr. Gordon’s strong leadership skills and extensive community involvement provide the Board of Directors with valuable insight into the needs of PCSB Bank’s local communities, particularly in Westchester County.

Directors Continuing in Office with Terms Expiring in 2021

Jeffrey D. Kellogg, age 7071 and a director since 2011, now retired, served as the Senior Vice President of Development and Community affairs at Putnam Hospital Center and as Executive Director of the Putnam Hospital Center Foundation. In this capacity, for 21 years, he was responsible for all fund-raising initiatives as well as the hospital’s marketing and communications, public relations, volunteer/auxiliary program, community outreach and guest services department. Professionally, in 2005 he was recognized as a Fellow of the Association for Philanthropy, which is the highest level of achievement in the field of health care philanthropy.

Before his positions with Putnam Hospital Center, Mr. Kellogg began his business career building and managing a chain of a dozen area sporting goods stores throughout Westchester, Dutchess and Putnam Counties in New York, and Fairfield County in Connecticut. Throughout his career he has been active in the community and has served on many boards and held numerous leadership positions. These include positions and membership with the Putnam County Economic Development Corporation,

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Mr. Kellogg’s strong leadership skills and extensive community involvement provide the Board of Directors with valuable insight into the needs of PCSB Bank’s local communities.

Robert C. Lusardi, Esq., age 6566 and a director since 2012, is a partner in the law firm of Daniels, Porco and Lusardi LLP located in Carmel, New York. He practices primarily in the areas of Real Estate and Zoning Litigation, Civil Litigation, Mortgage Foreclosure and Commercial Litigation. Mr. Lusardi is admitted to practice in New York, Connecticut and the U.S. District Courts for the Southern and Eastern Districts of New York. He has served as Assistant District Attorney, Putnam County, NY, Village Attorney, Village of Nelsonville Assistant Town Attorney, Town of Philipstown, and as a member of the Town of Putnam Valley Zoning Board of Appeals. He presently serves as Special Litigation Counsel and Zoning and Planning CounselTown Attorney to the Town of Putnam Valley. He is a member of the Carmel-Mahopac Chamber of Commerce, and the Putnam County and New York State Bar Associations. Mr. Lusardi attended The College of the Holy Cross where he received his B.A. and Syracuse University College of Law where he received his J.D.

Mr. Lusardi’s more than 4041 years of experience in commercial and real estate litigation provides the Board of Directors with valuable experience in real estate litigation matters as well as other legal matters.

Matthew G. McCrosson, age 6970 and a director since 2015, is a partner with MGM Advisory Services, LLC. Prior to this he was a partner with the accounting and advisory firm of PKF O’Connor Davies, LLP where he has beenwas employed since 2000. He provides performance improvement based advisory services in addition to organizational and operational reviews. He has assisted many clients in reviewing their technology platforms in terms of alternative systems and system selection and implementation coordination.

Before joining PKF O’Connor Davies, LLP in 2000, Mr. McCrosson was with KPMG Consulting, in the firm’s Public Services line of business. Earlier in his career, he served as chief financial officer and chief operation officer of several national and regionalnot-for-profit organizations. He serves on the Boards of the Business Council of Westchester and is President of the Westchester Community College Foundation. He is a past Chairman of the Westchester Community Foundation. Mr. McCrosson is a former director of CMS Bank, which was acquired by PCSB Bank in 2015.

The Board of Directors values Mr. McCrosson’s unique combination of financial and accounting expertise and knowledge of technology matters along with his designation as an “audit committee financial expert,” as that term is defined by Securities and Exchange Commission regulations.

Directors Continuing in Office with Terms Expiring in 2022

Joseph D. Roberto, age 67 and a director since 2012, has served as President and Chief Executive Officer of PCSB Bank since January 2012 and as its Chairman of the Board since January 2012 and has served as President, Chief Executive Officer and Chairman of the Board of the Company since its inception in 2017. He served as Chief Financial Officer of PCSB Bank from October 2005 to December 2011. His banking career spans more than 40 years serving in various financial management and executive positions for other financial institutions. Before joining PCSB Bank, he began his career at Yonkers Savings and Loan Association and served as Chief Financial Officer for both Yonkers Financial Corporation and Yonkers Savings and Loan Association, a public community bank, from 1996 to 2002. In 2004 and 2005 he served as Executive Vice President and Chief Financial Officer of Empire State Bank, a public commercial bank.

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Mr. Roberto is actively involved in various organizations in both Putnam and Westchester Counties, currently serving on the boards of the Putnam Economic Development Corporation, the Putnam Hospital Center Foundation, the Westchester County Association and the Boys and Girls Club of Mt. Vernon, NY. He is also actively involved with the American Heart Association and its Putnam Heart Walk, leading PCSB Bank’s efforts in fund raising and heart healthy awareness. Mr. Roberto has been recognized for his leadership and community involvement by many organizations including the NAACP Mount Vernon, NY Branch, the Boys and Girls Club of Mt. Vernon, NY, St. Christopher’s Inn, Garrison NY, Sunrise Association, Pearl River, NY, Northeast STEM Starter Academy at Mt. Vernon, Inc. and the Chabad of Bedford.

Mr. Roberto’s extensive knowledge of the banking industry and strong leadership skills provide the Board of Directors with invaluable insight and guidance into the business and regulatory requirements of today’s banking environment.

William V. Cuddy, Jr., age 61 and a director since 2015, serves as Executive Vice President of CBRE, Inc. providing commercial real estate consulting and brokerage services to corporations and other institutions for over 35 years. He leads a team of professionals in providing corporate real estate services including tenant representation as well as agency sales and leasing. CBRE, Inc. has recognized him as a top producing broker numerous times and he was awarded the NAIOP Deal of the Year six times for various sales and lease transactions.

Mr. Cuddy’s present and past leadership positions have included serving as a director of The Burke Hospital Foundation (2009-2018), a director of the Burke Research Institute (2006-2018), and a past director (2001-2009) and Chairman of The Burke Rehabilitation Hospital Board (2007-2009). He is a past President (2007) with the Friendly Sons of St. Patrick in Westchester County, a past Board member at Mercy College (1996-2005), and has been a director of the Westchester County Association since 2010. Mr. Cuddy is also a former director of CMS Bank which was acquired by PCSB Bank in 2015.

The Board of Directors values the depth of Mr. Cuddy’s background and expertise in real estate matters. In particular, he provides the Board of Directors with an extensive knowledge of the regional commercial real estate market, and provides valuable assistance in fostering relationships with owners, investors, developers and the corporate community. He is also valued for his marketing and transaction skills.

Kevin B. Dwyer, age 58 and a director since 2013, is the owner, manager of Dwyer Agency, LLC an insurance company and of Dwyer Agency of Mahopac, LLC, a real estate agency which have been providing Putnam County, New York and surrounding communities with residential and commercial real estate and insurance opportunities since 1927.

Mr. Dwyer is actively involved in many community organizations, serving on the Boards of Putnam Hospital Center Foundation, St. John’s Parish Mahopac Finance Committee, Friendly Sons of St. Patrick, Lake Mahopac Rotary, and Mahopac Chamber of Commerce. His professional organizations include New York State Commercial Association of Realtors, Hudson Valley Commercial Association of Realtors, New York State and National Association of Realtors, International Council of Shopping Centers and Independent Insurance Agents of New York State.

Mr. Dwyer’s real estate and insurance expertise provides the Board of Directors with valuable insight into the local real estate market and into the insurance needs of the Company and PCSB Bank.

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Willard I. Hill, Jr., age 65 and a director since 2017, now retired, is an attorney who served as Managing Director, Chief Marketing and Communications Officer and Head of Government Relations for MBIA Inc., a major financial guarantee insurance company. He previously served on MBIA’s executive management team as global Chief Compliance Officer, and separately as Head of Investor Relations. He retired from MBIA in 2013. Earlier in his career, he was president of the government deferred compensation business at ING US Financial Services (now Voya Financial) and he held senior executive positions in the legal and business divisions at Aetna, Inc.

Mr. Hill earned his MBA from the University of Connecticut School of Business in 1991. He earned a Juris Doctor from Howard University School of Law in 1979 and a B.A. from Fisk University in 1976. He is a member of the bar in several states, including New York. He serves as Board Secretary and Chairman of the Government Affairs Committee on the Board of Directors of the Council for Economic Education and previously served as Vice Chairman of Feeding Westchester.

Mr. Hill’s expertise in insurance and financial services, corporate law, government relations and strategic communications and his leadership experience as a senior executive with public companies is a significant strategic resource for the Board of Directors.

Named Executive Officers Who Do Not Serve as Directors

The following individuals have held their current positions for at least the last five years, unless otherwise stated. The ages presented are as of June 30, 2019.2020.

Michael P. Goldrick, age 54,55, has served as PCSB Bank’s Executive Vice President and Chief Lending Officer since October 2012. Before joining PCSB Bank, he held various management and executive positions in the banking industry since 1987 where he began his career at North Fork Bank & Trust Company as a loan officer. From 2001 to 2005, he was Vice President, Commercial Loans, M&T

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If the ratification of the appointment of the independent registered public accounting firm is not approvedratified by at least a majority of the votes cast at the annual meeting, the Audit Committee may consider other independent registered public accounting firms.

The Board of Directors unanimously recommends that stockholders vote “FOR” the ratification of the appointment of Crowe LLP to serve as the independent registered public accounting firm for the 20202021 fiscal year.

Audit Fees.The following table sets forth the fees billed by Crowe LLP for the fiscal years ended June 30, 20192020 and 2018:2019:

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EXECUTIVE COMPENSATION

We are an “emerging growth company,” as defined in the Jumpstart Our Business Startups Act of 2012, or the JOBS Act. As such, we are eligible to take advantage of certain exemptions from various reporting requirements that are applicable to other public companies that are not emerging growth companies. These include, but are not limited to, reduced disclosure obligations regarding executive compensation in our proxy statements, including the requirement to include a specific form of Compensation Discussion and Analysis, as well as exemptions from the requirement to hold a non-binding advisory vote on executive compensation. We have elected to comply with the scaled disclosure requirements applicable to emerging growth companies.

Introduction

The objective of our executive compensation program is to attract, retain, and motivate leaders who are committed to executing on our business strategy and creating long-term value for our stakeholders. To help us achieve these objectives, the Compensation Committee has designed an executive compensation program that consists of fixed and variable pay elements in the form of base salaries, annual cash and long-term equity incentives. We also provide retirement benefits that aid in the retention of our Named Executive Officers (“NEOs”), who are our Principal Executive Officer (“PEO”) (i.e., President and Chief Executive Officer) and the two most highly compensated other executive officers.

The following discussion provides an overview of our Compensation Committee’s philosophy and objectives in designing our compensation programs, as well as the compensation determinations and rationale for those determinations for our NEOs.

Governance Practices and Policies

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Role of Compensation Committee

The Compensation Committee determines the salaries and other forms of compensation to be paid each year to the PEO and those executive officers who report directly to the PEO. The Compensation Committee currently consists of Messrs. Weber (Chair), Weiss, Cuddy, Kellogg and Thimm. None of these individuals was an officer or employee of PCSB Financial Corporation or PCSB Bank during the fiscal year ended June 30, 2020, or is a former officer of PCSB Financial Corporation or PCSB Bank.

Each member of the Compensation Committee is an “independent director” as defined by the applicable rules and regulations of the NASDAQ, and meets the applicable standards of independence prescribed for purposes of federal securities, tax and other laws relating to the Compensation Committee’s duties and responsibilities.

The Compensation Committee is responsible for establishing and overseeing the executive compensation program, annually reviewing and approving the compensation of the PEO and reviewing and approving the recommendations regarding the compensation of the other senior executive officers. As part of that process, the Compensation Committee engages the services of an independent compensation consultant, Pearl Meyer & Partners LLC. (“Pearl Meyer”), to assist it in evaluating executive compensation programs and in making determinations regarding board of directors’ and senior executive officers’ compensation. While the Compensation Committee considers input from its independent compensation consultant, its final decisions are based upon many factors and considerations.

Role of Management

The PEO does not play any role in the Compensation Committee’s determination of his own pay. When appropriate, the Compensation Committee meets in executive session absent the PEO. The Compensation Committee does, however, solicit input from the PEO concerning the performance and compensation of the other senior executive officers. The PEO bases his respective recommendations on an assessment of each individual’s performance, external market pay practices, retention risk and the Company’s overall pay philosophy. All senior executive officer compensation decisions are ultimately approved by the Compensation Committee and the Board of Directors.

Role of Compensation Consultant

The Compensation Committee has the authority to retain and terminate a compensation consultant and to approve the consultant’s fees and all other terms of the engagement. Pearl Meyer, the independent compensation consultant, reports directly to the Compensation Committee. In addition to advising the Compensation Committee on compensation matters pertaining to the NEOs the consultant provided consulting advice concerning other key employees of the Company. This work was done with the prior knowledge and approval of the Compensation Committee and was not in conflict with the services provided to the Committee.

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The Compensation Committee has analyzed whether the work of Pearl Meyer as a compensation consultant has raised any conflict of interest, taking into consideration the following factors, among others: (i) the provision of other services to the Company by Pearl Meyer; (ii) the amount of fees the Company paid to Pearl Meyer as a percentage of Pearl Meyer’s total revenue; (iii) Pearl Meyer’s policies and procedures that are designed to prevent conflicts of interest; (iv) any business or personal relationship of Pearl Meyer or the individual compensation advisors employed by Pearl Meyer with an executive officer of the Company; (v) any business or personal relationship of the individual compensation advisors with any member of the Compensation Committee; and (vi) any stock of the Company owned by Pearl Meyer or the individual compensation advisors employed by Pearl Meyer. The Compensation Committee has determined, based on its analysis of the above factors, among others, that the engagement of Pearl Meyer and the work of the individual compensation advisors employed by Pearl Meyer as compensation consultants to the Company has not created any conflict of interest.

Benchmarking and Peer Groups

Pearl Meyer reviewed and recommended an appropriate peer group for assessing competitive compensation practices, and for making performance comparisons. The Compensation Committee used a regional peer group of 18 publicly traded thrift and banking institutions in the Northeast with average assets of $1.7 billion in comparing base salary and total compensation. Additional consideration was given to business model and performance.

The Compensation Committee evaluates the peer group annually for suitability and may modify peer groups from time to time based on mergers and acquisitions within the industry or other relevant factors. While our executive compensation program targets each NEO’s base salary, annual cash incentives and long-term equity compensation at median levels, actual compensation paid to a NEO may vary based on other factors, such as the individual’s performance, experience, responsibilities and competitive market conditions.

Components of the Compensation Program

During fiscal year 2020, our senior executive officer compensation program included four elements: base salary, annual cash incentives, equity awards, and benefit plans.

Base Salary. Senior executive officer base salaries are evaluated by the Compensation Committee on an annual basis. Salary ranges are developed by considering the results of an independent review of the competitiveness of the total compensation program for the position, as well as the overall importance of each position within the Company. The Compensation Committee then takes into consideration the senior executive officer’s performance and contribution to the long-term goals of the Company, leadership, operational effectiveness and experience in the industry, overall competitiveness with market levels, as well as recent operating results, performance targets and other relevant factors. The Compensation Committee also considers the compensation of our peer group.

Based on the foregoing, there was no base salary increase for Mr. Roberto in fiscal 2020. For Messrs. Nogles and Goldrick, in fiscal year 2020, the Compensation Committee determined that a 2.0% base salary increase was appropriate based on performance and the relationship of our compensation to our peers’ compensation.

Cash Incentive Plan. The Companymaintains a performance-based STIP for its senior executive officers. A major element of our compensation program is to make sure annual cash incentives are linked to the achievement of measurable corporate and individual goals set annually by the Compensation Committee. These goals include net income, growth in loans and deposits, net interest margin, efficiency and asset quality. During fiscal year 2020 each NEO was eligible to participate in the STIP.

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The Compensation Committee established and approved the Company’s performance metrics and goals at threshold, target and maximum performance levels for each NEO. The STIP is a balanced scorecard, which is based on a combination of Company and individual performance goals. The STIP also includes a performance trigger in order to activate the plan, requiring net income to be at least 87.5% of budgeted annual net income. Performance goals for the PEO are established solely by the Compensation Committee while the performance goals for the other NEOs are typically set by the Compensation Committee based on a recommendation of the PEO. Performance goals are communicated to officers during the first quarter of the fiscal year and achievement of goals is evaluated by the Compensation Committee after year-end.

For the fiscal year ended June 30, 2020 the performance goals for Messrs. Roberto and Nogles were net income, net interest margin, loan growth, retail deposit growth, fee income and efficiency ratio, comprising an 80% weighting, and a qualitative assessment of individual performance, comprising a 20% weighting. For Mr. Goldrick, the following performance goals were established: net income, organic loan origination, core deposit growth, loan fees and efficiency ratio, comprising an 80% weighting, and a qualitative assessment of individual performance, comprising a 20% weighting.

No awards are paid for performance below threshold for a particular performance measure but will be paid out for other performance measures provided threshold performance is obtained. Actual payouts for each goal are based upon final performance between threshold and maximum levels and are interpolated for any level of performance between threshold and maximum to reward incremental improvement. The Compensation Committee has the discretion to adjust any payouts to reflect the business environment and market conditions.

Each participant had a target award expressed as a percentage of earned base salary during the fiscal year and a range that defines the incentive opportunity. Actual awards vary based on performance and range from 0% of target (not achieving threshold performance for a goal) to 150% of target for exceptional performance. The Compensation Committee maintains the discretion to modify, decrease, increase or eliminate the award based on positive or negative performance of the Company or individual.

The following table provides information concerning the STIP opportunities for our NEOs during the fiscal year ended June 30, 2020:

Although credit quality remains extremely strong, the Company recorded a provision for loan losses in fiscal year 2020 to acknowledge the potential credit deterioration resulting from the economic outlook and forecast related to the COVID-19 pandemic, as well as the impact of unprecedented fiscal, monetary and regulatory interventions. This increase in the provision for loan losses was reflected in the Company’s overall performance in determining the bonus payments payable to the NEOs under the STIP for the fiscal year 2020. The Compensation Committee also used its discretion by imposing a downward adjustment to the bonus payments by eliminating the portion of the incentive associated with each of the NEO’s individual qualitative assessment, although performance for this component was largely satisfied by each NEO. As such, STIP payouts were adjusted to the following (as a percentage of base salary): Mr. Roberto 21.53%, Mr. Nogles 17.22% and Mr. Goldrick 19.37% .

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Equity Awards. We adopted a stockholder-approved equity incentive plan following our conversion from mutual to stock form of organization to promote the long-term financial success of the Company by providing a means to attract, retain and reward individuals who contribute to such success and to further align their interests with those of the Company’s stockholders through the ownership of additional common stock of the Company. We believe that equity grants with a time-based vesting feature awarded under the plan promotes executive retention because this feature incentivizes our executive officers to remain in our employment during the vesting period. Our NEOs have received awards in the form of restricted stock and stock options. During the fiscal year ended June 30, 2020, no equity awards were made to the NEOs.

Clawback Policy

We have a clawback policy that, in the event of a restatement of our financial statements to correct a material non-compliance with any applicable financial reporting requirement, allows the Compensation Committee to seek recovery or forfeiture from any senior executive officer of the portion of incentive compensation that was received by or vested in the executive officer during the three-year period prior to the determination that a restatement was required and that would not have been earned had performance been measured on the basis of the restated results.

Benefit Plans

The Company offers supplemental executive benefit plans in addition to benefit plans available to all employees. A summary of these programs is provided below.

Risk Assessment

The Compensation Committee believes that any risks arising from the Company’s compensation policies and practices are not reasonably likely to have a material adverse effect on the Company. In addition, the Compensation Committee believes that the mix and design of the elements of our executive compensation program do not encourage management to assume excessive risks. The Compensation Committee assesses risks posed by the compensation plans maintained for the benefit of, and incentive compensation paid to, officers and employees. The risk assessment conducted in fiscal year 2020 concluded that our incentive compensation plans provide incentives that appropriately balance risk and reward, are compatible with effective controls and risk management, and are supportive of strong governance, including active oversight by the Board of Directors.

Tax Deductibility of Executive Compensation

Under 162(m) of the Internal Revenue Code, as amended by the Tax Cut and Jobs Act (the “Tax Act”) on December 22, 2017, publicly-held corporations are subject to limits on the deductibility of executive compensation. Deductible compensation is limited to $1 million per year for each covered employee, defined as the publicly-held corporation’s principal executive officer, principal financial officer and three additional highest compensated officers during any taxable year of the corporation beginning after December 31, 2016. The Tax Act provides “grandfathered” treatment for certain compensation in excess of the $1 million deductibility limitation, including compensation that is “qualified performance-based compensation” within the meaning of Section 162(m) prior to the Tax Act, if payable pursuant to a written binding contract in effect as of November 2, 2017 that is not modified in any material respect thereafter.

While the Compensation Committee currently does not have a formal policy with respect to the payment of compensation in excess of the deduction limit under Section 162(m) of the Internal Revenue

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Code, the Compensation Committee’s historical practice has been to structure compensation programs offered to the NEOs with a view to maximizing the tax deductibility of amounts paid. However, in structuring compensation programs and making compensation decisions, the Compensation Committee considers a variety of factors, including the materiality of the payment and tax deductions involved and the need for flexibility to address unforeseen circumstances and our incentive and retention requirement for its management personnel. After considering these factors, the Compensation Committee may decide to authorize payments, all or part of which may be a nondeductible expense for federal tax purposes.

Summary Compensation Table.Table

The following information is furnished for the Company’s principal executive officer and for the two most highly-compensated executive officers (other than the principal executive officer) whose total compensation for the fiscal year ended June 30, 2019,2020, exceeded $100,000. These individuals are referred to in this proxy statement as the “named executive officers.”

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Employment Agreements. Messrs. Roberto, Nogles and Goldrick (each an “executive” and, collectively, the “executives”) have each entered into employment agreements with the Company and PCSB Bank. The agreements have a term that ends on December 31, 2020,2021, in the case of Mr. Roberto’s agreements, and December 31, 20192020 in the case of Messrs. Nogles and Goldrick’s agreements. Each agreement will extend automatically for one additional year on January 1 of each year beginning January 1, 2018 unless either the employers or the applicable executive gives notice no later than 90 days before such anniversary date that an agreement will not be renewed.

Each agreement specifies the executive’s base salary, which currently is $604,800$622,944 for Mr. Roberto, $319,949$326,348 for Mr. Nogles and $273,646$279,119 for Mr. Goldrick. The base salary will be reviewed not less frequently than once every twelve months and may be increased in the board’s discretion. In addition to the base salary, the agreements provide that the executives shall be eligible to participate in short-term and long-term incentive compensation, determined and payable at the discretion of the Compensation Committee. The executives shall also be entitled to continue participation in any fringe benefit arrangements in which they were participating on the effective date of the employment agreement. In addition, the agreements provide for reimbursement of reasonable travel and other business expenses incurred in connection with the performance of the executive’s duties. The agreements for Mr. Roberto provide that he will be entitled to a personal benefits allotment of $30,000 annually which will be used by him, in his sole discretion, towards a car allowance, country club membership, tax or financial advice or such other perquisites as he deems appropriate.

If the executive’s employment is terminated by PCSB Bank or the Company without cause, including a resignation for good reason (as defined in the agreement) during the term of the agreement, but excluding termination for cause or due to death, disability, retirement or following a change in control, the executive would be entitled to a payment equal to a multiple (i.e., three times for Mr. Roberto, two times for Mr. Nogles and one times for Mr. Goldrick) of the sum of: (i) his average base salary (or, in the case of Mr. Goldrick, his current base salary) plus (ii) his average annual incentive cash compensation awarded during the three (in the case of Mr. Roberto) and two (in the case of Messrs. Nogles and Goldrick) most recent fiscal years ending before the executive’s termination. The severance payment shall be paid to the executive within 30 days (or 60 days in certain circumstances) of the termination date, subject to the receipt of a signed release of claims from the executive within the time frame set forth in the agreement. In the case of Mr. Roberto, the payment shall also include a sum equal to three times his annual personal benefits allotment and a cash lump sum payment equal to the applicableco-payment percentage that PCSB Bank pays for his continuing life, medical and dental coverage, based on the costs of such coverage on the effective date of Mr. Roberto’s termination. Assuming Messrs. Nogles and Goldrick elect continued medical and dental coverage under COBRA, PCSB Bank and/or PCSB Financial will pay the applicable employerco-pay percentage for a period of 18 months, in the case of Mr. Nogles, and 12 months, in the case of Mr. Goldrick. Such coverage will be paid on apre-tax basis, if providing such coverage did not result in excise taxes or penalties to PCSB Bank or PCSB Financial, otherwise such coverage would be provided on anafter-tax basis. In addition, if Mr. Nogles elected continued COBRA coverage, PCSB Bank would also provide Mr. Nogles with a cash lump sum payment equal to the applicable employerco-pay percentage of such coverage for a period of an additional six months (based on the cost of such coverage at his termination date). PCSB Bank will also provide each executive with a cash lump sum payment equal to the cost of 24 months of life insurance premiums under the PCSB Bank-sponsored life insurance arrangements, in the case of Mr. Nogles, and 12 months, in the case of Mr. Goldrick (based on the cost of such coverage at the executive’s termination date). In addition, each executive would fully vest in any benefits under any nonqualified deferred compensation plans in which such executive is participating.

If the executive’s employment is terminated during the term of the agreement by PCSB Bank without cause, including a resignation for good reason (as defined in the agreements) within 24 months

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after a change in control (as also defined in the agreements), the executive would be entitled to a payment equal to a multiple (i.e., three times for Messrs. Roberto and Nogles and two times for Mr. Goldrick) of the sum of: (i) his current base salary (or his base salary in effect immediately before the change in control, if higher) plus (ii) his highest annual incentive cash compensation awarded during the three (in the case of Messrs. Roberto and Nogles) and two (in the case of Mr. Goldrick) most recent fiscal years ending before the executive’s termination. The severance payment shall be paid to the executive within five business days of the termination date. In the case of Mr. Roberto, the payment shall also include a sum equal to three times his annual personal benefits allotment and a cash lump sum payment equal to the cost of providing continued life, medical and dental coverage for 36 months following termination, at no cost to the executive, based on the costs of such coverage on the effective date of Mr. Roberto’s date of termination. Assuming Messrs. Nogles and Goldrick elect continued medical and dental coverage under COBRA, the employers will pay the entire cost of such coverage for a period of 18 months. Such coverage will be paid on apre-tax basis, if possible or if providing suchpre-tax coverage does not result in excise taxes or penalties to PCSB Bank or PCSB Financial. Otherwise such coverage would be provided on anafter-tax basis. In addition, if Messrs. Nogles and Goldrick elect continued COBRA coverage, the employers will also provide the executive with a cash lump sum payment equal to the cost of such coverage for a period of an additional 18 months, in the case of Mr. Nogles, and six months, in the case of Mr. Goldrick (based on the cost of such coverage at his termination date). The employers will also provide each executive with a cash lump sum payment equal to the premium cost for 36 months of life insurance coverage, in the case of Mr. Nogles, and 24 months, in the case of Mr. Goldrick (based on the cost of such coverage at the executive’s termination date). In addition, Messrs. Roberto and Nogles would fully vest in any benefits under any nonqualified deferred compensation plans in which such executive is participating.

For purposes of the executive’s ability to resign and receive a payment under the agreement, “good reason” would include the occurrence of any of the following events: (i) a failure of the employers to continue the executive in the executive’s position or, in the case of Messrs. Roberto and Nogles, the issuance by the employers of a notice to the executive that the term of the employment agreement will not be extended; (ii) a material adverse change in the nature or scope of executive’s responsibilities, title, authorities, powers, functions or duties or the duties normally exercised by someone in his executive position, without his consent, (iii) an involuntary reduction in his base salary, except in connection with anacross-the-board salary reduction affecting substantially all management employees and based on the employer’s financial performance, (iv) an involuntary relocation of executive’s principal place of employment by more than 35 miles driving distance from such office as determined at the date of the agreement, or (v) a material breach by the employers of the compensation provisions or any other provision of the agreement which continues for more than 10 days following notice given by the executive. If an event constituting “good reason” occurs, the executive is required to give the employers notice within 60 days and the employers will have 30 days to correct the good reason, however, the30-day period may be waived by the employers.

If the payments to the executives under their employment agreements with the employers made in connection with a change in control would result in an excise tax under Sections 280G and 4999 of the Code, the severance amounts payable to Messrs. Nogles and Goldrick would be reduced to avoid an excess parachute payment. The employment agreements with Mr. Roberto are silent with respect to any reduction.

If the executive is terminated due to disability, the employment agreement terminates. For these purposes, disability is defined as any medically determinable physical or mental impairment that can be expected to result in death or can be expected to last for a continuous period of not less than 12 months and that renders the executive unable to engage in any substantial gainful activity. If the executive dies while employed, the employers will continue to provide his base salary to his designated beneficiary for three months following his death.

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Upon retirement of an executive according to any retirement policy established by the employers’ boards and consented to by the executive, the executive will be entitled to benefits under any retirement plans to which he is a party but shall not be entitled to any amount or benefits under the employment agreement.

The employment agreements require the executives not to compete with PCSB Bank for a period of one year following a termination of employment for which the executive receives severance payments as the result of an involuntary termination or resignation for good reason (other than a termination of employment following a change in control). The employment agreements further require that the executives not solicit business, customers or employees of PCSB Bank or PCSB Financial for a12-month period following termination (other than a termination of employment following a change in control) and require the executives to maintain confidential information.

The employment agreements with PCSB Financial specify that there will be no obligation of payment or benefits paid under both the PCSB Bank and PCSB Financial employment agreements. To the extent that a payment is made by or a benefit is received from PCSB Bank, the same payment or benefit will not be paid by or received from PCSB Financial.

Supplemental Executive Retirement Plan for Joseph D. Roberto. PCSB Bank has adopted a Supplemental Executive Retirement Plan for Mr. Roberto. Under the Supplemental Executive Retirement Plan, which is a nonqualified deferred compensation plan subject to Section 409A of the Code, Mr. Roberto will be entitled to a normal retirement benefit if he separates from service after his normal retirement age of 68. The normal retirement benefit payable at age 68 is calculated as an annuity of $223,642 per year, payable in monthly installments for his lifetime with 15 years certain. If he separates from service before his normal retirement age (other than for cause or due to his death), his benefit will be reduced by 12.5% per year, for each year before his normal retirement age in which his separation occurs. If he works beyond his normal retirement age, his normal retirement benefit will be increased by multiplying the number of years beyond his normal retirement age that he works by 3% (i.e., retirement occurring five years beyond normal retirement age would result in a benefit equal to 115% of the normal retirement benefit). If PCSB Bank undergoes a change in control (as defined in the Supplemental Executive Retirement Plan), his benefit becomes fully vested. Upon Mr. Roberto’s separation from service, he will be entitled to a benefit equal to the normal retirement benefit. If he becomes disabled before attainment of his normal retirement age, his disability benefit would be equal to the benefit payable at his normal retirement age, payable in the form of a life annuity. If he is terminated for cause (as defined in the plan), he forfeits his right to any benefit under the Supplemental Executive Retirement Plan. Mr. Roberto’s right to a benefit under the Supplemental Executive Retirement Plan is conditioned on his agreement that for a period of one year following his termination of employment, he agrees not to solicit employees or customers of PCSB Bank to terminate their relationship with PCSB Bank, and further agrees not to otherwise compete with PCSB Bank within a 15 mile radius of the location in which PCSB Bank or its affiliates has business operations or has filed an application for regulatory approval to establish an office as of the date of his termination, provided that the requirement not to compete will not apply if his termination occurs following a change in control.

Contemporaneously with the adoption of the Supplemental Executive Retirement Plan, PCSB Bank purchased bank-owned life insurance and entered into a Supplemental Life Insurance Agreement (described below) with Mr. Roberto which would pay a death benefit to his beneficiary if he dies while employed at PCSB Bank. If he dies before retirement, his beneficiaries will receive a benefit under the life insurance agreement in lieu of any benefit under the Supplemental Executive Retirement Plan.

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In connection with the adoption of the Supplemental Executive Retirement Plan, Mr. Roberto entered into a participation agreement with PCSB Bank confirming his participation in the plan. The participation agreement permitted him to elect to receive his benefits under the plan in a lump sum payment rather than in a life annuity with 15 years certain. He has elected to receive a lump sum payment under each payment alternative set forth above.

Supplemental Life Insurance Agreement for Joseph D. Roberto.In conjunction with the adoption of the Supplemental Executive Retirement Plan for Mr. Roberto, PCSB Bank also entered into a Supplemental Life Insurance Agreement with Mr. Roberto. In connection with the adoption of the Supplemental Life Insurance Agreement, PCSB Bank acquired one or more life insurance policies on Mr. Roberto’s life. PCSB Bank is the owner of the policy or policies and has entered into an endorsement form with Mr. Roberto to endorse a portion of the death benefits to Mr. Roberto or his beneficiary (such arrangements are referred to as “split dollar agreements”). If Mr. Roberto dies before the payment of his retirement benefit commences under the Supplemental Executive Retirement Plan, his beneficiary would be entitled to a cash lump sum payment from the Supplemental Life Insurance Agreement, in lieu of any benefit under the Supplemental Executive Retirement Plan, equal to the lesser of (i) $2,517,841 or (ii) the net death proceeds available under the Supplemental Life Insurance Agreement. For these purposes, the “net death proceeds” are defined as the total death proceeds in the policy or policies on Mr. Roberto’s life, minus the greater of (i) the cash surrender value of the policy or (ii) the aggregate premiums paid by PCSB Bank on the policy or policies. If Mr. Roberto dies after his retirement benefits have commenced under the Supplemental Executive Retirement Plan, his beneficiary will be entitled to receive a benefit under the Supplemental Life Insurance Agreement equal to the lesser of (i) the present value of the remaining retirement benefits that would have been paid to him under the Supplemental Executive Retirement Plan had he lived for 15 years after retirement, using a 5% discount rate (or such other reasonable rate as the board determines) and (ii) the net death proceeds. Since Mr. Roberto has elected to receive his retirement benefit under the Supplemental Executive Retirement Plan in a lump sum payment following his separation from service, it is expected that no further benefit would be payable to him under this plan following his retirement.

Supplemental Retirement Plan for Senior Executives. PCSB Bank has adopted a Supplemental Retirement Plan for Senior Executives, effective January 1, 2017. Messrs. Nogles and Goldrick are the only participants in the Supplemental Retirement Plan for Senior Executives.

Under the Supplemental Retirement Plan for Senior Executives, which is a nonqualified deferred compensation plan subject to Section 409A of the Code, the participating executive will be entitled to a supplemental benefit, calculated as a fixed annual payment for 15 years, if he separates from service after reaching his benefit age (which is age 65 in the case of both Messrs. Nogles and Goldrick). The “supplemental benefit” for Messrs. Nogles and Goldrick is equal to an annual payment of $75,000 and $50,000, respectively. The normal form of benefit will be a single lump sum payment equal of the present value of the supplemental benefit unless the executive makes a timely election to be paid in 15 annual installments. If the executive has a separation from service before reaching his benefit age (other than due to death, disability, the occurrence of a change in control or for cause), the executive will be entitled to the supplemental benefit multiplied by his applicable vested percentage. The supplemental benefit will vest in each executive in equal percentages over a seven-year period.

If the executive dies before attaining his benefit age while employed at PCSB Bank, the executive’s beneficiary will be in entitled to the supplemental benefit and payment will commence on the first day of the second month following the executive’s death. If the executive dies following his separation from service and after becoming vested in any portion of the supplemental benefit but before commencement of benefit payments, the executive’s beneficiary will be entitled to the amount otherwise payable to the executive and payment will commence on the first day of the second month following the executive’s death.

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If the executive becomes disabled before separation from service and before reaching the benefit age, the executive will receive the supplemental benefit as if the executive had reached his benefit age before disability. The payment will be made in a lump sum either within 30 days of the disability determination or at age 65, in accordance with the executive’s election set forth in his participation agreement.

If PCSB Bank has a change in control (as defined in the Supplemental Retirement Plan for Senior Executives) and the executive’s employment is involuntary terminated (including a good reason termination by the executive) following the change in control, the executive will be entitled to the supplemental benefit, calculated as if executive had attained his benefit age at the time of separation from service. If the executive’s employment is terminated within two years following the change in control, the executive’s benefit will be the present value of the supplemental benefit paid in a lump sum within 30 days following separation from service. If the executive’s employment terminates more than two years following the change in control (other than due to death or disability), the executive will be entitled to the supplemental benefit, payable in the manner set forth in the executive’s participation agreement for benefits payable on a “separation from service prior to benefit age” or “separation from service on or after benefit age”, as applicable. If a change in control occurs after the executive commences receiving the supplemental benefit paid in the form of installment payments and the executive has made an election in the participation agreement to receive a lump sum payment of the remaining amounts due following a change in control, the present value of the remaining payments will be determined and made payable no later than 30 days after the occurrence of the change in control.

If the executive is terminated for cause, he forfeits his rights to any benefit under the Supplemental Retirement Plan for Senior Executives. The benefits provided under the Supplemental Retirement Plan for Senior Executives are conditioned on the executive’s covenant that for a period of one year following the executive’s termination of employment (other than following a change in control), the executive will not compete with PCSB Bank in any city, town, or county in which the executive’s normal business office is located and PCSB Bank or the Company has an office or has filed an application for a regulatory approval to establish an office. In addition, the executive shall not hire or attempt to hire any employee of PCSB Bank or solicit any business from any customer of PCSB Bank or their subsidiaries.

Supplemental Life Insurance Plan. PCSB Bank maintains a Supplemental Life Insurance Plan for the benefit of certain executives, other than Mr. Roberto, who have been selected to participate in the plan. Messrs. Nogles and Goldrick are participants in the Supplemental Life Insurance Plan, which provides for a death benefit payment equal to the lesser of: (i) one andone-half times a participant’s highest rate of base salary, as in existence in the 2015 calendar year, or (ii) the executive’s net death proceeds if he dies while employed with PCSB Bank. For these purposes, the “net death proceeds” are defined as the total death proceeds in the officer’s policy minus the greater of the cash surrender value of the policy or the aggregate premiums paid by PCSB Bank on the policy. An officer’s participation in the Supplemental Life Insurance Plan will terminate: (i) if any regulatory agency requires PCSB Bank to sever its relationship with the executive; (ii) if PCSB Bank is subjected to regulatory restrictions limiting its ability to pay the compensation under the plan; (iii) in the event of insolvency, receivership or dissolution of PCSB Bank, (iv) upon termination of the executive’s employment, or (v) as otherwise may be determined by PCSB Bank’s Board of Directors in good faith.

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in the pension plan with respect to individuals hired after October 1, 2012 (i.e., a “soft freeze”). In connection with the soft freeze, employees of PCSB Bank before October 1, 2012, who completed one year of service, attained age 21, and were not in one of the excluded classifications were (and remain) eligible to accrue benefits under the pension plan. On February 15, 2017, PCSB Bank froze participation in the pension plan to all employees on May 1, 2017 (i.e., a “hard freeze”). After the hard freeze, no further benefits will accrue to the benefit of participants. Contributions to the Plan will continue to be made, if necessary, to satisfy the actuarially determined minimum funding requirements according to the Employee Retirement Income Security Act of 1974, as amended (“ERISA”). A participant will become 100% vested in his or her accrued benefit under the plan after five years of service with PCSB Bank.

Under the terms of the frozen plan, upon attainment of normal retirement age (age 65) or upon termination after early retirement age (age 60), a participant who is not married and has accrued benefits of more than $1,000 will receive a life annuity for the participant’s life, unless the participant elects another form of payment. If the participant is married and the present lump sum value of his accrued benefit exceeds $1,000, the normal form of payment will be a joint and survivor annuity, with a percentage of the participant’s benefit continuing to the participant’s spouse upon the participant’s death. If the participant’s vested account balance is $1,000 or less, the participant will receive a cash distribution as soon as practicable. A participant’s accrued benefit will become fully vested upon the participant’s death. If a participant dies while the participant is still employed by PCSB Bank or if the participant dies after he or she retires or terminates employment but before benefit payments start, the surviving spouse will be entitled to a life annuity based on the value of the participant’s vested accrued benefit.

The basic normal retirement benefit is calculated by multiplying the participant’s average of his highest three consecutive years of service by 2% for each year of credited service, up to a maximum of 30 years. A reduced benefit is payable upon early retirement at or after age 60. In the event of late retirement, the late retirement benefit will be the actuarial equivalent of the basic normal retirement benefit plus credit for accruals after attainment of normal retirement age.

401(k) Plan. PCSB Bank maintains a 401(k) Plan, which is a qualified,tax-exempt profit sharing plan with a salary deferral feature under Section 401(k) of the Code (the “401(k) Plan”). All employees who have attained age 21 and completed one year of eligibility service except for union employees, leased employees, and employees compensated on an hourly or commission basis are eligible to participate in the plan. Employees may make elective salary deferrals in an amount no less than 1% of compensation and up to the lesser of 25% of compensation (as defined by the 401(k) Plan) or $18,000 (as indexed). Employees who have attained age 50 before the end of a plan year are also eligible to makecatch-up contributions during the year in an amount not to exceed $6,000 (as indexed). All employee elective salary deferrals andcatch-up contributions are fully and immediately vested.

In addition, until July 1, 2018, PCSB Bank made an employer matching contribution equal to 75% of up to 6% of a participant’s compensation that the participant defers to the plan. The employer matching contribution was discontinued effective July 1, 2018. In addition, employees who were hired on or after October 1, 2012, who were not eligible to participate in the pension plan due to its “soft freeze,” received an additional profit sharing contribution equal to 5% of their compensation. However, this additional profit sharing contribution was discontinued in 2017. Profit sharing contributions and employer matching contributions are subject to asix-year vesting schedule. Participants are entitled to benefit payments upon termination of employment due to normal retirement at or after age 65, early retirement at or after age 60, disability or death. Benefits will be distributed in the form of lump sum, which is the normal form of distribution, or installment payments at the election of the participant.

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offering. Eligible employees who had attained age 21 and had completed one year of eligibility service on or before April 20, 2017, the closing date of the initial public offering, began to participate in the employee stock ownership plan, retroactively, as of January 1, 2017, the plan’s effective date. All employees, except for union employees, leased employees and employees compensated on an hourly basis or commission basis, are eligible to participate. Employees who did not satisfy the eligibility requirements on April 20, 2017 will become eligible to enter the plan on the first entry date commencing on or after both attainment of age 21 and completion of one year of service.

The employee stock ownership plan trustee purchased, on behalf of the employee stock ownership plan, 1,453,209 shares of the Company’s common stock issued in the initial offering with the proceeds of a loan from the Company equal to the aggregate purchase price of the common stock. The loan will be repaid principally through PCSB Bank’s contribution to the employee stock ownership plan and dividends payable on common stock held by the employee stock ownership plan over the anticipated15-year term of the loan. Currently, the interest rate for the employee stock ownership plan loan is an adjustable-rate equal to the prime rate, as published inThe Wall Street Journal, on April 20, 2017. The interest rate will adjust annually and will be the prime rate on the first business day of the calendar year, retroactive to January 1 of such year. The trustee will hold the shares purchased by the employee stock ownership plan in an unallocated suspense account and will release the shares from the suspense account as the employee stock ownership plan repays the loan. The trustee will allocate the shares released among participants based on each participant’s proportional share of compensation relative to all participants. Participants will become 100% vested in their benefit after six years of credited service. Participants also will become fully vested upon normal retirement, death or disability, a change in control, or termination of the employee stock ownership plan. Generally, participants will receive distributions from the employee stock ownership plan after severance from employment.

Outstanding Equity Awards at June 30, 20192020

The following table provides information regarding equity awards outstanding as of June 30, 20192020 to each named executive officer.

2933

OTHER INFORMATION RELATING TO DIRECTORS AND EXECUTIVE OFFICERS

Section 16(a) Beneficial Ownership Reporting Compliance

General.Section 16(a) of the Securities Exchange Act of 1934 requires the Company’s executive officers and directors, and persons who own more than 10% of any registered class of the Company’s equity securities, to file reports of ownership and changes in ownership with the Securities and Exchange Commission. These individuals are required by regulation to furnish the Company with copies of all Section 16(a) reports they file.

Delinquent Section 16(a) Reports. Based solely on its review of the copies of the reports it has received from and written representations provided to it from the individuals required to file the reports, the Company believes that each of its executive officers and directors has complied with applicable reporting requirements for transactions in the Company’s common stock during the fiscal year ended June 30, 2019.2020, except for the following individuals who inadvertently failed to file timely reports as follows: Mr. Cuddy (one Form 5 to report 15 acquisitions under the Director Fee Deferral Plan and one Form 4 to report one open market acquisition); Mr. Dwyer (one Form 5 to report eight acquisitions under the Director Fee Deferral Plan); Ms. Gordon (one Form 5 to report eight acquisitions under the Director Fee Deferral Plan); Mr. Hill (one Form 5 to report eight acquisitions under the Director Fee Deferral Plan); Mr. Kellogg (one Form 5 to report eight acquisitions under the Director Fee Deferral Plan); Mr. Lusardi (one Form 5 to report 16 acquisitions under the Director Fee Deferral Plan); Mr. McCrosson (one Form 5 to report 16 acquisitions under the Director Fee Deferral Plan and one Form 4 to report one open market acquisition); Mr. Thimm (one Form 5 to report eight acquisitions under the Director Fee Deferral Plan); Mr. Weber (one Form 5 to report eight acquisitions under the Director Fee Deferral Plan); Mr. Weiss (one Form 5 to report eight acquisitions under the Director Fee Deferral Plan); and David R. McNamara, Senior Vice President/Compliance Officer (one Form 4 to report one open market sale). Each individual with acquisitions under the Director Fee Deferral Plan subsequently reported all of his or her acquisitions on a Form 4.

Transactions with Related Persons

Loans and Extensions of Credit. Federal law generally prohibits publicly traded companies from extending credit to their executive officers and directors, but it contains a specific exemption from the prohibition for extensions of credit made by federally insured financial institutions, such as PCSB Bank, to their executive officers and directors in compliance with federal banking regulations. However, it is the policy of PCSB Bank not to extend credit to its directors and executive officers and their related interests.

Other Transactions. Mr. Lusardi is a partner in the law firm of Daniels, Porco and Lusardi LLP, which received legal fees from the Company and PCSB Bank aggregating approximately $54,000$34,000 for the fiscal year ended June 30, 2019.2020.

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SUBMISSION OF BUSINESS PROPOSALS AND STOCKHOLDER NOMINATIONS

We must receive proposals that stockholders seek to include in the proxy statement for the Company’s next annual meeting no later than May 13, 2020.27, 2021. If next year’s annual meeting is held on a date that is more than 30 calendar days from October 23, 2020,28, 2021, a stockholder proposal must be received by a reasonable time before we begin to print and mail our proxy solicitation materials for such annual meeting. Any stockholder proposals will be subject to the requirements of the proxy rules adopted by the Securities and Exchange Commission.

Our Bylaws provide that, for a stockholder to make nominations for the election of directors or proposals for business to be brought before the annual meeting, a stockholder must deliver notice of such nomination and/or proposals to the Corporate Secretary not less than 90 days nor more than 120 days before the date of the annual meeting. However, if less than 90 days’ notice or prior public disclosure of the annual meeting is given to stockholders and the date of the annual meeting is advanced more than 30 days before or delayed more than 30 days after the anniversary of the preceding year’s annual meeting, such notice must be delivered not later than the close of business on the tenth day following the day on which notice of the annual meeting was mailed to stockholders or public disclosure of the annual meeting date was made. A copy of the Bylaws may be obtained by contacting the Company’s Corporate Secretary.

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Please vote today by marking, signing, dating and promptly returning the enclosed proxy card in the enclosed envelope, or by voting by Internet or by telephone.

By Order of the Board of Directors,

Clifford S. Weber

Corporate Secretary

Yorktown Heights, New York

September 10, 201924, 2020

3136

PCSB FINANCIAL CORPORATION

CONFIDENTIAL ESOP VOTING INSTRUCTIONS

SOLICITED ON BEHALF OF THE TRUSTEE OF THE

PCSB BANK EMPLOYEE STOCK OWNERSHIP PLAN (“ESOP”) FOR

THE ANNUAL MEETING OF STOCKHOLDERS TO BE HELD ON OCTOBER 23, 201928, 2020

Dear ESOP Participant:

On behalf of the Board of Directors of PCSB Financial Corporation (the “Company”), you are receiving the attached Vote Authorization Form to convey to Pentegra Trust Company (the “ESOP Trustee”) your voting instructions on the proposals to be presented at the Company’s Annual Meeting of Stockholders to be held at the Company’s headquarters at 2651 Strang Blvd., Suite 100, Yorktown Heights, New York on Wednesday, October 23, 201928, 2020 at 11:00 a.m., Eastern Daylight Time (“EDT”).Time.

The PCSB Bank Employee Stock Ownership Plan (the “ESOP”) allows participants to direct the ESOP Trustee how to vote the shares of Company common stock that have been allocated to the participants’ ESOP accounts. You are entitled to instruct the ESOP Trustee how to vote the shares of Company common stock allocated to your account as of August 23, 2019,21, 2020, the record date for stockholders entitled to vote at the Annual Meeting, by completing and returning the ESOP Vote Authorization Form.

The ESOP Trustee has appointed American Stock Transfer & Trust Company, LLC (“AST”) as its agent to receive the ESOP Vote Authorization Forms and to tabulate the results. To direct the voting of the shares of Company common stock allocated to your account, you must either complete, sign and date the ESOP Authorization Form and return it in the accompanying postage-paid envelope to AST or you may provide your voting instructions via the Internet or by telephone, as described on the enclosed ESOP Vote Authorization Form. In any event, your voting instructions must be received no later than 11:59 p.m., EDT,Eastern Time, on Wednesday, October 16, 2019.21, 2020.

The ESOP Trustee will vote the shares of Company common stock allocated to participants’ accounts in accordance with the timely received and completed voting instructions, so long as such vote is in accordance with the provisions of the Employee Retirement Income Security Act of 1974, as amended (“ERISA”).

IF YOU VOTE BY RETURNING THE ESOP VOTE AUTHORIZATION FORM, IT MUST BE RECEIVED BY AST NO LATER THAN 11:59 P.M., EDT,EASTERN TIME, ON WEDNESDAY, OCTOBER 16, 2019, 21, 2020, WHICH IS SEVEN (7) DAYS BEFORE THE ANNUAL MEETING DATE. YOUR INDIVIDUAL VOTE WILL NOT BE REVEALED TO THE COMPANY.COMPANY.

Your confidential vote and the votes of other participants will be tallied by AST and the results provided to the ESOP Trustee who will: