On July 5, 2023, Community Bank System, Inc. (the “Company”) announced that Mark E. Tryniski will retire as the Company’s President and Chief Executive Officer (“CEO”) effective as of December 31, 2023. Since August 2006, Mr. Tryniski has served as the President, CEO and Director of the Company and its wholly owned banking subsidiary, Community Bank, N.A. (the “Bank”). The Board of Directors (the “Board”) has selected Dimitar A. Karaivanov, the Company’s Executive Vice President and Chief Operating Officer (“COO”), to succeed Mr. Tryniski effective as of January 1, 2024.

In addition, the Board will expand to 13 Directors and appoint Mr. Karaivanov as a Director of the Company and the Bank effective as of January 1, 2024. In connection with Mr. Karaivanov’s promotion, the Company and the Bank entered into a new Employment Agreement with him, effective as of January 1, 2024 (the “Employment Agreement”). The Employment Agreement provides that Mr. Karaivanov shall serve as the President and CEO of the Company and the Bank during the period from January 1, 2024 to December 31, 2026.

Mr. Karaivanov, age 41, joined the Company in June 2021 as its Executive Vice President of Financial Services and Corporate Development, responsible for the business and financial performance of three of the Company’s four business lines – benefits administration, insurance services, and wealth management. In October 2022, he was appointed COO, adding responsibility for the Company’s banking business – Community Bank, N.A. Prior to joining the Company, Mr. Karaivanov served as Managing Director in Lazard’s Financial Institutions Group and has extensive experience as an investment banker for banks, other financial institutions, and fintech companies at a number of leading financial services firms. Mr. Karaivanov holds an MBA degree from The Ohio State University Max M. Fisher College of Business. He is also a graduate of the American Bankers Association’s Stonier Graduate School of Banking.

Mark joined the Company in 2003 as its Chief Financial Officer and has been at the helm since 2006. Under his leadership, the Company has grown from $4.2 billion in total assets to over $15.2 billion in total assets today. Mark is the architect of the Company’s core values of integrity, excellence, teamwork, and humility and has created a corporate culture that embodies these values and an executive team that is poised for continued success.