Community Financial System invests $37.35 million in Leap Holdings

SYRACUSE, N.Y. - Community Financial System, Inc. (NYSE:CBU), a financial services company with a market capitalization of $3.2 billion and a solid dividend yield of 3.1%, announced Monday it has made a minority investment of approximately $37.35 million in Leap Holdings, Inc., acquiring various classes of preferred and common stock in the Delaware corporation.

The investment aligns with Community Financial System’s strategy to expand its diversified financial services portfolio, particularly complementing its existing insurance services business. According to InvestingPro data, CBU has demonstrated strong financial health with revenue growth of 8.4% in the last twelve months.

Leap Holdings’ wholly owned subsidiary, Leap Insurance Agency, LLC, operates as a technology-focused managing general agent (MGA) providing insurance solutions for the rental housing sector. The company offers products including Agile Rent Guaranty, where Leap acts as a co-signer for renters, and Leap Deposit Replacement, which substitutes traditional security deposits with monthly payments.

These solutions are backed by insurance company capacity rated A- (Excellent) by A.M. Best, provided through the Accelerant Risk Exchange. Leap has been operating since 2018.

Community Financial System is a diversified financial services company with approximately $16 billion in assets. Its banking subsidiary, Community Bank, N.A., operates about 200 customer facilities across Upstate New York, Northeastern Pennsylvania, Vermont, and Western Massachusetts. InvestingPro analysis indicates the stock is currently trading below its Fair Value, with impressive dividend credentials including 27 consecutive years of dividend increases and 42 years of consistent dividend payments. For detailed insights and more exclusive metrics, investors can access the comprehensive Pro Research Report, available for CBU among 1,400+ top US stocks.

The company’s other business lines include employee benefit services through Benefit Plans Administrative Services, Inc., insurance services via OneGroup NY, Inc., and wealth management services through its Nottingham Financial Group unit.

This information is based on a press release statement from Community Financial System. The company maintains a conservative debt profile with a debt-to-equity ratio of 0.48, and analysts have recently revised their earnings expectations upward for the upcoming period, according to InvestingPro data, which offers additional valuable insights through its extensive financial metrics and analysis tools.

In other recent news, Community Financial System reported its second-quarter 2025 earnings, delivering an earnings per share (EPS) of $1.04, which exceeded analysts’ expectations of $1.01. However, the company’s revenue fell short, reaching $199.3 million compared to the anticipated $201.23 million. Raymond James reiterated its Strong Buy rating on Community Financial, setting a price target of $73.00, despite the core EPS falling slightly below both their estimates and consensus expectations. Meanwhile, Keefe, Bruyette & Woods (KBW) adjusted their price target for Community Financial to $67.00 from $69.00, maintaining a Market Perform rating, and noted that net interest income and credit performance were in line, counterbalancing weaker fee income. Additionally, Community Financial announced the planned retirement of Jeffrey M. Levy, its Senior Vice President and Chief Banking Officer, effective December 31, 2025. Levy has been with the company in various roles, including President of Commercial Banking and Regional President of the Capital Region of New York. These developments reflect ongoing changes and evaluations within Community Financial System.

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