Director of Payment Operations

Career Opportunities with Chesapeake Bank

A great place to work.

Salary Range: $88,200 - $141,200

Chesapeake Bank – Kilmarnock/Williamsburg/Richmond

Most “Payments Director” postings ask you to run a function that's already built - optimize it, keep it compliant, keep it quiet. This one is different:
Chesapeake Bank is handing someone the keys to build payments as a business, which will allow us to innovate while supporting the growth and financial goals of our customers.

We processed over $40 billion in payments in 2025, and we’re looking to you to help us grow that number even further. You'll have the backing of a high-performing community bank ready to support the vision, so your job is to define, plan and execute on it. If you've worked in a larger institution where payments innovation moved at the speed of committee, this is the opposite: direct access to leadership, real authority, and the freedom to deliver.

One payments strategy, owned end to end

• Set the roadmap across ACH, wire, RTP/Fed Now, card, and whatever comes next
• Pick the orchestration and processing partners that let us move fast without changing core systems
• Own the numbers that matter and report on them directly to leadership

• Work shoulder-to-shoulder with AML, Operations, Treasury Management, Compliance and Fraud so controls are designed in, not bolted on after an exam finding
• Represent payments in front of regulators and examiners as the person who actually built the program, not someone reading from a binder

• Make important decisions about our ACH and Faster Payments programs that will allow us to meet our customers’ needs today and in the future
• Help design and launch third-party sender (TPS) facilitation for our merchant acquiring division– the risk and underwriting frameworks, the monitoring, the agreements. You write the playbook.
• Position Chesapeake Bank as the payments provider for all of our bank-owned subsidiaries by handling disbursements, collections, reconciliation – making it easy for them to partner and use our services.

• You’ll work closely with Treasury, Operations, Risk, Fraud, and Technology teams to help Chesapeake evolve from traditional business-hours payment processing to a model that supports customers in an increasingly real-time economy. As payment activity moves beyond the confines of the banking day, you’ll help design the processes, controls, and partnerships that enable treasury and liquidity services to respond effectively around the clock.

• 7+ years in payments, treasury management, merchant services, or bank operations leadership – with real, hands‑on experience in ACH/faster payments in a complex payments environment
• You know NACHA rules, card network rules, and instant payments operating requirements well enough to build a program around them, not just follow one
• You’ve supervised employees for 5+ years, and have experience developing talented, high-performing teams
• You hold certifications such as the AAP, APRP, or AFPP
• You've evaluated or implemented a payments orchestration or core platform and can speak to what mattered in that decision
• You think like a business owner: you can build a P&L case, negotiate a vendor contract, and hold your own in front of a board
• You've built something new inside a regulated environment before, and you know how to move fast without creating your own exam finding
• You genuinely like working across AML, Fraud, and Operations teams – this role doesn't work for someone who'd rather go around them
• You understand treasury and liquidity fundamentals well enough to lead a team through what changes when customers expect access around the clock, not just during business hours

• Direct ISO/merchant acquiring TPS or payment facilitator (Pay Fac) experience
• Factoring, asset-based lending, or commercial finance payment flow experience
• Community or mid-size bank experience – you know how to build without a big-bank…