Here are 1-2 brief analogies for Orange County Bancorp:

• Bank of America, but specifically focused on New York's Hudson Valley region.
• A community-focused JPMorgan Chase for Orange County, New York.

• Lending Services (Credit Products): Providing various types of loans, including commercial real estate, commercial and industrial, construction, and residential mortgages, to businesses and individuals.
• Deposit Services (Funding Products): Offering a range of deposit accounts, such as checking, savings, money market, and certificates of deposit, to attract funds from individuals and businesses.
• Wealth Management & Trust Services: Delivering investment management, financial planning, and trust administration services to help clients manage and grow their assets.
• Treasury Management Services: Providing specialized financial tools and services for businesses to manage their cash flow, payments, and liquidity efficiently.

Orange County Bancorp (symbol: OBT) operates as a bank holding company. As a financial institution, its customer base is highly diversified and typically does not consist of a few identifiable "major customers" in the traditional sense, as customer relationships are broad and confidential. Instead, it serves a wide range of individuals and businesses within its operational footprint.

The company primarily serves the following categories of customers:

• Individuals and Households: This category includes consumers seeking traditional banking services such as checking and savings accounts, certificates of deposit, residential mortgages, home equity lines of credit, and personal loans.
• Small to Medium-sized Businesses (SMBs): This segment encompasses local businesses of various sizes and industries that utilize commercial loans, lines of credit, business checking and savings accounts, treasury management services, and other business banking solutions to manage their operations and growth.
• Commercial Real Estate Investors and Developers: This category includes individuals and entities involved in the acquisition, development, and management of commercial properties. Orange County Bancorp provides financing for commercial real estate projects, including construction loans, term loans for income-producing properties, and real estate lines of credit.

• Crowe LLP (Private Company)

Michael Gilfeather President, Chief Executive Officer & Director

Mr. Gilfeather has served as President and Chief Executive Officer of Orange County Bancorp and its subsidiary bank since April 2014. He brings over 35 years of experience in the banking sector to his leadership position. Prior to joining Orange County Bancorp, Mr. Gilfeather was the Chief Administrative Officer and Executive Vice President at Hudson Valley Bank, where he was responsible for the branch network, training and development, human resources, and the trust department. He was part of the team responsible for Hudson Valley Bank's growth and transformation into a $2.6 billion, 28-branch banking operation. Before his time at Hudson Valley Bank, he spent 20 years with The Bank of New York, serving as Senior Manager for all retail banking in Manhattan. Mr. Gilfeather holds an MBA in Finance from Pace University and a Bachelor of Science in Psychology from Union College. He served as Chairman of the New York Bankers Association from 2021-2023 and concluded a three-year chairmanship of the Orange County Partnership in 2022. He also serves as a director of Hudson Valley Investment Advisors. Under his leadership, Orange Bank & Trust Company has expanded its presence in the Hudson Valley, focusing on commercial lending and community development.

Michael Lesler Executive Vice President, Chief Financial Officer

Mr. Lesler was appointed Senior Vice President and Chief Financial Officer in March 2023. He previously served as Senior Vice President, Controller and Chief Accounting Officer for Orange County Bancorp and its bank subsidiary starting in December 2021. Mr. Lesler possesses over 20 years of experience in the banking industry. Before joining Orange County Bancorp, he held the position of Executive Vice President and Chief Operating Officer for BCB Bancorp, Inc. from 2018 to 2021, and prior to that, he served in the same role at Clifton Bancorp, Inc. from 2016 to 2018.

Michael Coulter Executive Vice President, Strategic Lending Relationship Executive

Mr. Coulter joined Orange Bank & Trust Company in April 2017 as Senior Vice President and Chief Lending Officer and was promoted to Executive Vice President and Chief Lending Officer in February 2019. He brings over 35 years of experience in banking. Prior to his tenure at Orange County Bancorp, Mr. Coulter served as Executive Vice President of Metropolitan Bank in Manhattan. He also held increasingly senior positions at BBVA Compass Bank, Sun National Bank, Citizens, and Key Bank in the greater New York City and Hudson Valley markets.

David Dineen Executive Vice President, Community Banking Officer

Mr. Dineen most recently served as Senior Vice President, Market Manager at Republic Bank, where his responsibilities included treasury management, lending, and the establishment of their Private Banking group. Previously, he was Executive Vice President, Community Banking Officer at Bankwell Financial, where he was part of the executive team overseeing 12 branch offices, training, deposit operations, and treasury management. Before Bankwell, Mr. Dineen spent 10 years at Capital One Bank as an Executive Vice President, holding various roles that included branch and small business banking for the New York and Connecticut markets.

Mr. Listner Senior Vice President and Chief Credit Officer

Mr. Listner has served as the Senior Vice President and Chief Credit Officer of Orange Bank & Trust Company since March 2020. He initially joined the Bank in 2018 as 1st Vice President and Senior Credit Officer. Prior to joining Orange County Bancorp, Mr. Listner was a Senior Vice President, Senior Relationship Manager at Sun National Bank from 2011 to 2014 and again from 2016 to 2018. He also served as Senior Vice President, Senior Relationship Manager with BBVA from 2015 to 2016.

Legal & Regulatory Risk

Orange County Bancorp's top identified risk category is Legal & Regulatory. This type of risk involves potential changes in laws, regulations, or regulatory enforcement that could negatively impact the company's operations, compliance costs, or business model. For financial institutions, regulatory scrutiny and evolving legal landscapes are constant challenges.

Interest Rate Risk

The company is exposed to interest rate risk, particularly concerning its adjustable-rate loans. While these loans aim to mitigate the bank's exposure to interest rate fluctuations, rising interest rates can increase borrowers' payments, thereby increasing the potential for loan defaults.

Credit Risk

Orange County Bancorp also faces credit risk, especially with its consumer loan portfolio. Consumer loans generally carry higher credit risk due to the nature or absence of collateral and typically have shorter terms and higher interest rates. This increases the potential for losses if borrowers are unable to repay their loans.

Orange County Bancorp (OBT) operates in the Lower Hudson Valley region and the New York metropolitan area, including Orange, Westchester, Rockland, and Bronx counties in New York, as well as nearby markets in Connecticut and New Jersey. The company's main products and services include commercial and consumer banking, with a focus on commercial real estate loans, commercial and industrial loans, residential real estate loans (mortgages), and wealth management services.

The addressable markets for Orange County Bancorp's main products and services are sized as follows:

• Commercial Banking (New York): The market size for the Commercial Banking industry in New York is estimated at $259.1 billion in 2025. This market encompasses deposits from customers and the issuance of consumer, commercial, and industrial loans.
• Commercial and Industrial Lending (United States): Commercial lending represented 44.34% of the US commercial banking market share in 2024. The total US commercial banking market is estimated at USD 732.5 billion in 2025, with a forecast to reach USD 915.45 billion by 2030.
• Commercial Real Estate Lending (New York City / United States): In August 2022, the largest lenders in New York City originated approximately $3.8 billion in commercial real estate financing. Nationally, multifamily properties represent the largest asset class of maturing loans, with $113 billion expected to mature in the next 24 months, followed by office ($46.6 billion), hotel ($42.3 billion), and retail ($31.0 billion).
• Residential Mortgages (United States): The US home loan market is projected to reach USD 2.29 trillion in 2025 and is forecasted to grow to USD 3.02 trillion by 2030. The total outstanding balances for residential mortgages in the United States of America attained a value of approximately USD 12.85 trillion in 2023. New York is considered a significant market for residential mortgages due to its large and diverse population.
• Wealth Management (North America): North America is a significant region for wealth management, expected to contribute 42% to the global market's growth between 2022 and 2027. The global wealth management market size is projected to increase by USD 460.1 billion, growing at a CAGR of 8.5% from 2024 to 2029.

Orange County Bancorp (OBT) is expected to drive future revenue growth over the next 2-3 years through several key strategies:

1. Loan Portfolio Expansion: The company has demonstrated consistent growth in its loan portfolio. In the third quarter of 2025, total loans increased by $119.9 million (6.6%) to $1.9 billion compared to December 31, 2024. Similarly, the second quarter of 2025 saw total loans grow by 5.6% to $1.9 billion. Analysts and investors view the bank's ability to expand its loan portfolio as a key growth prospect.
2. Deposit Growth: Alongside loan growth, Orange County Bancorp has been successful in increasing its deposit base. Total deposits rose by $125.5 million (5.8%) to $2.3 billion as of September 30, 2025, from December 31, 2024. This trend was also evident in the second quarter of 2025, with deposits increasing 5.7% to $2.3 billion, and in the first quarter of 2025, with a 6.0% growth in deposits.
3. Net Interest Margin (NIM) Enhancement: Orange County Bancorp has shown an ability to expand its net interest margin, which directly contributes to higher net interest income. The net interest margin grew by 45 basis points to 4.26% in the third quarter of 2025, compared to the same period in 2024. In the second quarter of 2025, a robust net interest margin of 4.06% was reported. This indicates effective management of interest-earning assets and funding costs.
4. Growth in Wealth Management and Advisory Services: The company's wealth management division, which includes Hudson Valley Investment Advisors (rebranded to Orange Investment Advisors in October 2025), is a driver of non-interest income. Trust and investment advisory income increased by 14.8% to $3.4 million in the second quarter of 2025, with total assets under management reaching $1.8 billion. The first quarter of 2025 also reported a significant rise of 19.2% in this income category.
5. Strategic Market Expansion: Orange Bank & Trust Company has been expanding its physical presence by adding branches in new geographical areas. Recent expansions include new offices in Rockland, Westchester, and the Bronx, with a new full-service office in the Bronx celebrated in October 2025. This strategic branch expansion aims to capture new customers and market share, leading to increased revenue.

Share Issuance

• In June 2025, Orange County Bancorp completed an underwritten public offering of 1,720,430 shares of its common stock at $23.25 per share, generating approximately $40.0 million in gross proceeds.
• The underwriters fully exercised their overallotment option in June 2025, leading to the sale of an additional 258,064 shares, which provided approximately $5.7 million in proceeds after underwriting discounts and commissions.
• The total $46 million follow-on common stock offering in Q2 2025 was undertaken to strengthen the company's financial position, with net proceeds intended for general corporate purposes, including investments in Orange Bank & Trust Company to support growth, augment regulatory capital and liquidity, and potentially fund strategic acquisitions.

Inbound Investments

• As of March 28, 2025, institutional investors collectively held 3,043,627 shares of Orange County Bancorp.
• Major institutional shareholders include Hudson Valley Investment Advisors Inc /adv, BlackRock, Inc., and Wellington Management Group Llp.
• During Q1 2025, Jacobs Levy Equity Management Inc. increased its stake by 230.7%, acquiring an additional 8,569 shares valued at $287,000, while MIRAE ASSET GLOBAL ETFS HOLDINGS Ltd. also boosted its holdings by 107.9%, purchasing 3,132 additional shares worth $141,000.

Capital Expenditures

• Orange County Bancorp's capital expenditures growth is forecasted to be 31.2%, with an expected average growth of 9.9% over the next five fiscal years.
• The company opened new full-service offices in the Bronx and hosted a ribbon-cutting ceremony for its newly renovated headquarters in Middletown in 2025, indicating investments in expanding and upgrading its physical infrastructure.
• Historically, "significant investments in people, systems and expanding our geographic footprint" contributed to balance sheet growth and profitability between 2018 and March 2021.