You are currently viewing Profile: Dimitar Karaivanov

Profile: Dimitar Karaivanov

New Community Bank System’s CEO looks to build on past success, plans to expand in Albany and other markets

By Stefan Yablonski

The new president and CEO of Community Bank System Inc. is 42 and came to the United States about 20 years ago for grad school.

Dimitar Karaivanov was born and raised in Bulgaria.

“I came over to my new homeland for my MBA, which I did at the Ohio State University,” he said. “Ohio State was a great experience.”

Karaivanov is also a graduate of the American Bankers Association’s Stonier Graduate School of Banking.

“I’m privileged to be in Syracuse, New York, working at this wonderful company,” he said.

He spent 15 years on Wall Street, working with financial services companies including Community Bank System — “which is how I got to know the company and management really well,” he said.

He joined the company from Lazard Middle Market, where he served as a managing director and member of the Financial Institutions Group since June 2018.

Prior to Lazard, he spent more than a dozen years in investment banking at a number of leading financial services firms after he began his career in public accounting.

“I met my wife during a two-year stint in Philadelphia. We have three young kids — two boys [9 and 6] and a girl [2.5]. We have really enjoyed our move to Upstate and the kindness of the people,” he said.

“And my wife is actually from Canada, so snow and cold is her kinda thing,” he laughed. “It’s a nice move here; she’s closer to family and friends. She was born in Calgary.”

Small world

“One of our neighbors is also Bulgarian and there is another one like just five minutes away from where we are as well,” he said. “What are the chances that you move to Central New York and within a five-minute radius there are three people from your home country?”

He was always fascinated by the exposure one got from working as a trusted adviser to companies, he explained of his career path.

“I did not have specific plans to work in banking, but have always strongly believed in the apprenticeship model in my career,” he said. “It just so happened that the best mentors I found when I was a junior employee were in the financial services space and I chose to follow their path. And then I had the unbelievable opportunity to move from an adviser to an operator at Community Bank System.”

Community Bank System, Inc. is a diversified financial services company based in DeWitt. It’s focused on four main business lines — banking, benefits administration, insurance services and wealth management. Total assets at Community Bank exceeds $15 billion.

“Numbers are just numbers. The responsibility we all have — and me in particular, is to our clients, colleagues and communities,” he said. “That is the duty of care I am focused on and that is what drives our culture and ultimately performance and growth. Keeping that ground level mindset is imperative for our long-term success.”

He hopes to build on the work done by his predecessor, longtime CEO Mark Tryniski, who retired at the end of 2023.

“I was fortunate when I was in my investment banking shoes to have Community Bank as one of my clients and get to know the company and Mark [Tryniski] and the team pretty well over those years,” Karaivanov said. “I worked with them on most of the important decision points in the company’s development over that time and got to know the culture.”

Karaivanov said during that time at Lazard, they were writing a letter together outlining the reasons to partner with Community Bank and listing the company’s successes.

“Typically, you list all kinds of reasons why you want to do that,” he said.

At the top of one of those letters, Karaivanov said Tryniski wrote, “humility of management.”

“That took me a little bit of time to process — what does that really mean? I was very much struck by that approach. That’s one of the main reasons why I’m here,” he said. “It’s one of our core values.”

“We have a tremendous set of foundational values in our company — integrity, teamwork, excellence and humility. The first two are the most common. Humility is very rare, in fact this is the only company that I’ve seen that uses that word as a core value,” he added.

“We also have a truly enviable business and competitive position across our banking, benefits administration, insurance and wealth businesses,” he continued. “The plan is to keep building upon all of that; empower and grow our main asset — our people, leverage data in everything we do and adhere to our core values.”

For example, he pointed to the company’s big push into the Albany area.

“Absolutely. We have plans to expand in all of our larger markets,” he said. “We have had great success in Albany and love to invest behind success. We continue to grow the team. In fact, we recently added a leader for our retail banking business for Albany and are actively looking at additional locations.”

For him, free time can be a scarce commodity.

“Between being a glorified chauffeur for all the kids’ activities and focus on the company there frankly isn’t a ton of free time,” he quipped. “I do like to read, both professionally to learn from others and also for entertainment — historical fiction and sci-fi are
my favorites.”

As part of Karaivanov’s initial three-year employment agreement, he will have an annual base salary of at least $900,000, according to filings with the U.S. Securities and Exchange Commission.

He joined Community Bank in June 2021 as its executive vice president of financial services and corporate development. He assumed leadership responsibilities for the company’s non-banking subsidiaries and financial services businesses and operations, including the employee benefit services and institutional trust businesses, the wealth management and investment advisory businesses and the insurance and risk management businesses.

He was promoted to executive vice president and chief operating officer Oct. 1, 2022. In this role, Karaivanov had oversight responsibilities for all banking, wealth management, employee benefit services, insurance operations and related business activities.

He became CEO of the bank Jan. 1.

Community Bank System, Inc. operates more than 230 customer facilities across Upstate New York, northeastern Pennsylvania, Vermont and Western Massachusetts through its banking subsidiary, Community Bank, N.A.

The DeWitt headquartered company is among the country’s 125 largest banking institutions.

Community Bank System, Inc. is listed on the New York Stock Exchange and the company’s stock trades under the symbol CBU.


Name: Dimitar Karaivanov,

Position: President and CEO Community Bank System, parent company of Community Bank NA

Birth place: Bulgaria

Residence: Syracuse area

Education: MBA from Ohio State University

Personal/family: Wife; two sons and a daughter

Hobbies: Reading