President, Chesapeake Payment Systems

Chesapeake Financial Shares • Williamsburg, VA

13d

About The Position

Chesapeake Bank - Chesapeake Payment Systems President, Chesapeake Payment Systems Become the visionary guiding one of the most respected payment divisions in the industry. Chesapeake Bank is seeking an exceptional candidate to lead Chesapeake Payment Systems Acquiring Division—someone known not only for their deep expertise, but for their reputation across the payments ecosystem. This is a rare opportunity for an accomplished industry figure to shape strategy, elevate market presence, and drive innovation in a division recognized for its integrity, performance, and forward‑thinking approach. As the senior leader of our payments division, you will be the driving force behind its growth, innovation, and national prominence. You will guide experienced teams through change and opportunity, champion a culture of excellence, and set the tone for collaboration, accountability, and forward-thinking execution. Your leadership will influence strategy, strengthen industry relationships, and ensure our organization remains a respected name in an evolving payments environment. If you're a strategic mind with a passion for developing people, cultivating partnerships, and amplifying organizational impact, this is your moment to step into a role where your leadership truly matters. Why You’ll Love It Here: We’re consistently ranked among the top 200 banks in the U.S. for employee engagement Competitive pay, great benefits, and real opportunities to grow A culture of giving back: we invest time and money into the communities we serve A collaborative executive team that values your input Want to read more about why you should join the team, click the link below: Top 10 Reason You Should Explore a Career with Chesapeake Bank At Chesapeake Bank, we believe in more than just numbers—we believe in people. Join us and help shape what’s next for Chesapeake Payment Systems. Summary: Manages the payments division of Chesapeake Bank, Chesapeake Payment Systems (CPS). Encourages the growth, performance, and profitability of the CPS division and all related services. Stays abreast of the product landscape and industry changes as it relates to payments business products and services. Manages the development and implementation of new services that achieve the goal of client acquisition, and retention. Ensures CPS remains in a recognized and respected position in the national payments’ ecosystem. Manages resource growth needs and promote increased staff skill levels from all employees while maintaining a level of accessible and engaged leadership qualities.

Requirements

• Essential experience/skills necessary to perform the role Bachelor's degree in business or equivalent combination of education or experience.
• Minimum of 10 years in payments, financial services, or related industries, with at least 5 years in senior leadership roles.
• Involvement in or with a sponsor bank preferred.
• Deep network of relationships across the payments and financial services industry.
• Being a recognized, respected and engaged leader in acquiring payments industry.
• Proven ability to lead and inspire teams, make strategic decisions, and drive results.
• Strong interpersonal skills and the ability to collaborate across business units, functions and levels.
• Excellent written communications and presentation skills.

Responsibilities

• Strategic Leadership: Develop and execute the divisions’ long-term vision, mission, and strategic goals, encompassing merchant acquiring, ACH processing support, real-time and faster payment capabilities, and hybrid disbursement methods.
• Collaborate with the Chesapeake Bank Senior Management team and the divisions’ leadership team to align division business strategies with the overall Chesapeake Financial Shares strategies.
• Collaborate with marketing leadership to develop and plan relevant communications that appropriately promote and message the value of Chesapeake Payment Systems products and services.
• Payment Partnerships: Foster strong relationships with merchant partners, acquirers, payment networks, and regulatory bodies across merchant acquiring and the payment industry.
• Stay informed about industry trends, competitive landscape, and regulatory changes specific to merchant acquiring, ACH, real-time payments, and disbursements.
• Continually assess and refine business product lines and the ability to meet evolving market needs and competitive landscape across all lines of payment services.
• Financial Oversight: Responsible for the Profit & Loss statement for Chesapeake Payment Systems, to meet revenue and budget targets.
• Optimize revenue streams, profitability, and cost management across all payment services.
• Operational Excellence: Lead division managers to streamline processes for merchant onboarding, transaction processing, ACH settlement support, and disbursements.
• Maintain high-quality service delivery in all payment areas.
• Risk Management: Proactively manage risks associated with merchant relationships, ACH transactions, and disbursement processes.
• Implement and ensure adherence with robust risk management practices and a culture of compliance.
• People Leadership: Inspire, motivate and demonstrate a diverse team focused on merchant acquiring and payment processing.
• Foster a positive work culture that encourages innovation, collaboration, and professional growth.
• Board Engagement: Report periodically to the board of directors, including the Acquiring Review Committee of the Board of Directors, providing regular updates and seeking their guidance on critical matters related to all payment areas.
• Understand your role as defined by the three lines of defense to maintain a compliance culture that includes risk management processes
• Other duties as assigned

Benefits

• Competitive pay, great benefits, and real opportunities to grow
• A culture of giving back: we invest time and money into the communities we serve
• A collaborative executive team that values your input

What This Job Offers

• Job Type: Full-time
• Career Level: Executive