Question 1

What is Chesapeake Bank?

Accepted Answer

Chesapeake Bank is a community-focused commercial bank serving central and eastern Virginia. With over $1.6 billion in assets and 19 branches, it operates as the principal subsidiary of Chesapeake Financial Shares, Inc. (OTCQB: CPKF).

The bank specializes in serving small businesses, consumers, and families across Virginia's Northern Neck, Middle Peninsula, Williamsburg, Richmond, Chesterfield, and Peninsula regions. Beyond traditional banking, Chesapeake operates three specialty divisions: Chesapeake Wealth Management (wealth management and trust services), Chesapeake Payment Systems (merchant processing), and Flexent (accounts receivable financing).

Question 2

When was Chesapeake Bank founded?

Accepted Answer

Chesapeake Bank was originally chartered as Lancaster National Bank on April 13, 1900, making it the first national bank on Virginia's Northern Neck. The bank was founded with $25,000 in investments from local citizens to serve the watermen, oystermen, fishermen, and farmers of the region.

In 1968, Lancaster National Bank merged with Chesapeake Banking Company of Lively to form Chesapeake National Bank. The institution adopted its current name, Chesapeake Bank, in 1994 when it dropped "National" from its name and converted to a state charter under Federal Reserve supervision.

Throughout its 120+ year history, the bank has weathered significant challenges, including the 1917 Great Irvington Fire (when it operated from a tent to continue serving customers) and the Great Depression, demonstrating remarkable resilience and commitment to its communities.

Question 3

Where is Chesapeake Bank headquartered?

Accepted Answer

Chesapeake Bank is headquartered at 97 North Main Street, Kilmarnock, Virginia 22482. The Kilmarnock location, often called the "Main Branch" or "Headquarters," is home to the bank's senior leadership, including President Jeffrey M. Szyperski.

The headquarters building houses multiple lines of business, including Wealth Management and Residential Lending operations. The main office was relocated to its current Kilmarnock address on May 19, 1980.

Question 4

Where does Chesapeake Bank operate?

Accepted Answer

Chesapeake Bank operates exclusively throughout Virginia, with 19 branches and offices across six key regions:
• Northern Neck: Four branches including the Kilmarnock headquarters, serving Lancaster County and surrounding areas
• Middle Peninsula: Three branches serving Mathews and Gloucester counties
• Williamsburg area: Five branches including locations at Five Forks, Lafayette, and Lightfoot
• Richmond: Four branches providing urban market services
• Chesterfield County: Branch serving the growing suburban market (opened 2021)
• Peninsula: Loan production office in Newport News (opened 2023)

The bank also serves customers nationally through its Flexent division, which provides accounts receivable financing to businesses across the United States with offices in Virginia and Texas.

Question 5

What services does Chesapeake Bank offer?

Accepted Answer

Chesapeake Bank provides comprehensive banking services across multiple categories:

Retail Banking: Interest and non-interest checking accounts, savings accounts, money market accounts, certificates of deposit, and personal loans.

Commercial Banking: Commercial loans, commercial real estate financing, single-family residential construction loans, business checking and savings, and specialized lending to industries including retail, medical, hospitality, agriculture, and marine sectors.

Mortgage Services: Residential mortgage loans, home equity products, and construction financing.

Digital Banking: The ChesBank Mobile app and online banking platform, powered by Q2 Holdings' digital banking technology, offers mobile check deposit, bill pay, peer-to-peer payments through Zelle, account transfers, debit card management, digital wallet integration (Apple Pay, Samsung Pay, Google Pay), and ATM/branch locators.

Specialty Services:
• Chesapeake Wealth Management: Brokerage, trust, and estate management services (established 1973)
• Chesapeake Payment Systems: Merchant processing, point-of-sale systems, and payment solutions for businesses nationwide (launched 1997)
• Flexent: Accounts receivable financing and cash flow management solutions (introduced 1995)

The bank also operates six branches within continuing care retirement communities (CCRCs) to serve senior residents.

Question 6

What makes Chesapeake Bank unique?

Accepted Answer

Historic Innovation: In 1968, Chesapeake launched the nation's first "Boat 'n Bank"—a floating branch with its home port at Carter's Creek Marina in Irvington—to serve workers at the oyster packing plant and the region's maritime community. This exemplifies the bank's tradition of creative solutions for local needs.

Digital Transformation Leadership: Chesapeake has invested significantly in technology, implementing Q2 Holdings' best-in-class commercial banking platform in 2020. The bank provides customers with digital experiences comparable to major tech companies like Amazon, Netflix, and Google, while maintaining its community bank values.

Recognition and Leadership: The bank has been named one of American Banker's "Top 200 Community Banks" for 15 consecutive years and recognized as a "Best Bank to Work For" for 10 consecutive years. President Jeffrey M. Szyperski served as the 2018-19 Chairman of the American Bankers Association, representing community banks nationally and meeting with world leaders.

Diversified Business Model: Unlike typical community banks, Chesapeake generates substantial revenue from three specialty divisions—payment processing, wealth management, and accounts receivable financing—providing stability and growth beyond traditional banking.

Community Commitment: Operating under the philosophy "It's All About Community," the bank encourages all 235+ associates to volunteer locally and actively supports community development in every market it serves.

Question 7

What type of financial institution is Chesapeake Bank?

Accepted Answer

Chesapeake Bank is a State-Chartered Commercial Bank and member of the Federal Reserve System. The bank holds FDIC Certificate #6862 and operates under the supervision of the Federal Reserve Board (FRB).

As a commercial bank, Chesapeake focuses primarily on lending to small businesses while also serving retail customers. Its state charter (converted from national charter in 1994) provides flexibility in operations while maintaining federal oversight. The bank operates as the principal subsidiary of Chesapeake Financial Shares, Inc., a publicly-traded bank holding company (OTCQB: CPKF).

The institution exemplifies the community bank model—locally managed, relationship-focused, and deeply committed to regional economic development—while offering the sophisticated products and technology typically associated with larger institutions.

Question 8

What recognition has Chesapeake Bank received?

Accepted Answer

Chesapeake Bank has earned numerous prestigious industry recognitions that validate its performance and culture:

American Banker has recognized Chesapeake as one of the "Top 200 Community Banks" in the United States for 15 consecutive years based on return on equity and financial performance. The bank has also been named a "Best Bank to Work For" by American Banker for 10 consecutive years, reflecting its strong employee satisfaction and workplace culture.

The Richmond Times-Dispatch has honored Chesapeake as a "Top Small Workplace" for five consecutive years, highlighting the bank's positive work environment.

Aite Group has recognized Q2 Holdings (Chesapeake's digital banking platform provider) multiple times as a leading provider of U.S. cash management technology, indirectly validating Chesapeake's technology infrastructure choices.

Leadership recognition includes President Jeffrey M. Szyperski's tenure as 2018-19 Chairman of the American Bankers Association, where he represented community banks nationally and advocated for the industry with world leaders and banking groups globally.

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