COMMUNITY FINANCIAL SYSTEM, INC.

For the period ended May 20, 2026. Filed Mar 27, 2026.

About this filing

What shareholders are asked to vote on at a company's meeting. It is where to find what directors and top executives are paid, and who owns the most shares.

May 20, 2026 · Filed Mar 27, 2026

CBU$64.74+0.2%Stored close · as of Nov 6, 2026

See the whole filing, with its images and exhibits

Contents

Cover page

Show cover page

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:

☐	Preliminary Proxy Statement

☐	Confidential, For Use of the Commission Only (as permitted by Rule 14a-6(e)(2))

☒	Definitive Proxy Statement

☐	Definitive Additional Materials

☐	Soliciting Material Pursuant to §240.14a-12

(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 all boxes that apply):

☒	No fee required.

☐	Fee paid previously with preliminary materials.

☐	Fee computed on table in exhibit required by Item 25(b) per Exchange Act Rules 14a-6(i)(1) and 0-11.

333 Butternut Drive

Syracuse, New York 13214

Dear Shareholders:

The Annual Meeting of the Shareholders of Community Financial System, Inc. (the “Company”) will be held virtually on Wednesday, May 20, 2026 at 12:00 p.m. Eastern Daylight Time.

Whether or not you plan to attend the Meeting, the Board of Directors strongly encourages you to review the enclosed information and vote your shares. Your vote is important.

2025 PERFORMANCE HIGHLIGHTS:

In 2025, the Company continued to strategically invest across our businesses, advancing our core investment thesis of generating above-average returns while maintaining below-average risk. The Company deployed capital in each of our four business lines—banking, employee benefit services, insurance services, and wealth management services—with a focus on building recurring fee income streams that support sustainable, long-term growth.

The banking business in particular experienced significant investment and growth. The Company opened 15 new branches and successfully completed the acquisition of seven branch locations from Santander Bank, N.A., accelerating our strategic expansion in the Greater Lehigh Valley region. These initiatives, combined with solid loan and deposit growth, resulted in a more than 22% increase in operating pre-tax income, positioning the banking business for accelerated growth. We also enhanced our insurance services revenue stream through a minority investment in Leap Holdings, Inc., a technology-driven managing general agent specializing in providing insurance solutions for the rental housing sector. This investment aligns with our goal of expanding and diversifying our fee-based revenue.

Additionally, in January 2026, the Company announced an agreement to acquire ClearPoint Federal Bank & Trust. This acquisition will significantly broaden the range and scale of our wealth management services, further strengthening our ability to deliver value to our clients and shareholders. These recent investments and acquisitions underscore our commitment to building meaningful fee-based businesses that will have a direct and positive impact on the Company’s bottom line.

In addition to the investments noted above, the Company achieved the following milestones in 2025:

•	The banking, insurance services, and wealth management services each had very strong years with all of those businesses ahead of industry metrics and peers in net profits generated by each line of business;

•	Produced year-over-year increases in diluted GAAP earnings per share, diluted operating earnings per share and operating pre-tax, pre-provision net revenue per share:

•	Increased diluted GAAP earnings by $0.53 or 15.4%;

•	Increased diluted earnings per share by $0.59 or 16.2%;

•	Increased operating pre-tax, pre-provision net revenue per share by $0.79 or 15.3%;

•	Increased total operating revenues by $72.1 million or 9.7%;

•	Continued to maintain robust regulatory capital ratios;

•	Increased loans outstanding by 5.0%;

•	Leveraged the strength of our core deposit base, driving a year-over-year increase in net interest income for the 19th consecutive year;

•	Increased the cash dividend to our Shareholders by 2.2% in the third quarter, marking the 33rd consecutive year of dividend increases. The Company’s unbroken streak places it in a very select group, and signifies the Company’s commitment to robust Shareholder returns; and

•	Recognized by Forbes Magazine as one of America’s Best Banks.

CORPORATE AND GOVERNANCE DEVELOPMENTS:

Over the past five years, the Board has executed a disciplined approach to enhance its collective skills, experience, and composition by adding five new directors, including, most recently, the following two appointments:

•	In October 2025, the Board welcomed John A. Vaccaro, former head of MassMutual Financial Advisors and former CEO of MML Investors Services, LLC. Mr. Vaccaro brings deep expertise in wealth management, insurance, business strategy, financial oversight, and regulatory compliance.

•	In March 2026, Brenda M. Hall, former Executive Vice President and Chief Operating Officer of Standard Lines at Selective Insurance Group, Inc., joined the Board. Ms. Hall offers valuable insights into the insurance industry and extensive C-suite leadership experience.

Together with the Board, we thank you for your continued interest and support. We remain committed to serving your interests and focused on creating long-term value for all Shareholders.

Sincerely,

Eric E. StickelsChair of the Board	Dimitar A. Karaivanov President and Chief Executive Officer

333 Butternut Drive Syracuse, New York 13214

NOTICE OF ANNUAL MEETING OF SHAREHOLDERS

To the Shareholders of Community Financial System, Inc.:

Community Financial System, Inc., a Delaware corporation (the “Company”), will hold its annual meeting of Shareholders virtually on Wednesday, May 20, 2026 at 12:00 p.m. Eastern Daylight Time for the following purposes:

1.	To elect 12 of the current Directors for a one (1) year term and until their successors are elected and qualified;

2.	To hold an advisory vote on executive compensation;

3.	To ratify the appointment of PricewaterhouseCoopers LLP as the Company’s independent registered public accounting firm for 2026; and

4.	To transact any other business which may properly come before the Meeting or any adjournment thereof.

The Shareholders of record at the close of business on March 23, 2026 are entitled to notice of, and to vote at, the Annual Meeting or any adjournment or postponement thereof.

Important Notice Regarding the Availability of Proxy Materials for the Shareholder Meeting to be Held on May 20, 2026. The Company uses the “notice and access” delivery method which allows the Company to furnish proxy materials (the Proxy Statement, Form 10-K, and Annual Report) electronically via the Internet.

•	If you received a Notice of Internet Availability of Proxy Materials by mail, you will not receive a printed copy of the proxy materials in the mail unless you specifically requested them.

•	The Notice of Internet Availability of Proxy Materials contains instructions on how you can access the proxy materials on the Internet, as well as instructions on obtaining a paper copy of the proxy materials.

Whether or not you plan to attend the Annual Meeting virtually, please submit your proxy promptly so that your shares will be voted as you desire.

By Order of the Board of Directors

Danielle M. Cima

Secretary

March 27, 2026

IMPORTANT NOTICE

The Company urges you to please vote your shares now whether or not you plan to attend the Meeting virtually. Voting by the Internet or telephone is fast and convenient. If you request to receive a paper copy of the proxy materials, you may also vote by completing, signing, dating and returning the accompanying proxy card in the return envelope furnished for that purpose. If you hold your shares through an account with a broker, bank or other holder of record, please follow the instructions you receive from them to vote your shares. Please vote your shares so your vote can be counted.

ContentsView on SEC.gov

The text of this filing, as the company filed it with the SEC, without its images or exhibits. This is not investment advice.