Director OF Operations

Career Opportunities with Chesapeake Bank A great place to work. Careers At Chesapeake Bank Join Our Team as a Director of Payment Operations! Salary Range: $88,200 - $141,200 Chesapeake Bank – Kilmarnock/Williamsburg/Richmond Build Your Own Opportunity 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. What You'll Build One payments strategy, owned end to end Set the roadmap across ACH, wire, RTP/FedNow, 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 Real partnership, not red tape 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 Support our growth 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. A payments model built for an always-on world 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. What Makes You the Right Fit 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 Especially interested in candidates with: Direct ISO/merchant acquiring TPS or payment facilitator (PayFac) 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 budget or headcount, and you're energized by that constraint rather than limited by it Why Chesapeake Chesapeake Bank is a $1.7+ billion, high‑performing community bank headquartered in Kilmarnock, VA, and it's investing seriously in payments and digital transformation as a growth strategy, not a defensive one. This role sits at the center of that investment: direct visibility to leadership, a mandate to build rather than maintain, and the kind of scope that would take a decade to earn at a larger institution. Beyond that, we’re “people” people, not a “bank” bank. We want the best for our employees and customers because we believe that a rising tide lifts all boats. There is opportunity for growth and we’ll invest in you if you decide to bring your talents to Chesapeake Bank. Ready to Make a Difference? The Director of Payment Operations provides leadership for Chesapeake Bank's payment ecosystem, overseeing payment operations, payment strategy, and related infrastructure. The role is responsible for ACH, card services, instant payments (RTP/FedNow), and emerging payment technologies, ensuring payment activities are secure, scalable, efficient, and compliant. The Director oversees payment operations for the core bank and collaborates with affiliated business units, including Chesapeake Payment Systems and Flexent, to support payment initiatives and strategic growth opportunities. Working across multiple business lines, the Director drives payment innovation, supports vendor and third‑party payment programs, and advances strategic initiatives that enhance the customer experience, manage risk, and support the Bank's growth objectives This position requires significant experience in payments, banking operations, treasury management, regulatory compliance, and third-party risk management, as well as the ability to lead complex cross‑functional initiatives and drive organizational change. Responsibilities: Own the enterprise payments roadmap across ACH, wire, RTP/FedNow, card, and emerging rails Assist in the development of the bank's approach to continuous treasury management, including liquidity positioning, lending capacity, and working capital tools, to meet customer expectations created by instant payments availability outside of traditional business hours Manage payments orchestration and processing vendors/platforms; evaluate available orchestrators and/or payment technologies on an ongoing basis Develop and track payments‑related KPIs (volume, revenue, loss rate, exception rate, SLA performance) and report on these to executive leadership Design the operational, risk, and underwriting framework required to facilitate third‑party sending (TPS) Assist with the onboarding due diligence standards and ongoing monitoring procedures, in coordination with Chesapeake Payment Systems and the Bank’s AML and Fraud teams As owner of the payments program, ensure compliance with all applicable rules, regulations, and network requirements Design and implement the payments infrastructure (disbursements, collections, reconciliation) to serve both customers and other lines of business Develop the internal business case and operating agreement governing the relationships between the bank and other business units Own this relationship on an ongoing basis, including issue resolution and volume/performance reporting Partner with Operations leadership on staffing, systems, and process design to support payments volume growth Manage vendor relationships and contract negotiations for payments processing, orchestration, and monitoring tools Maintain documentation of payments procedures sufficient to support internal audit and regulatory exam requests Escalate emerging payments risk issues to appropriate leadership and committees in a timely manner Partner with stakeholders across the organization to ensure controls are embedded in new payment products and third‑party relationships at design stage Represent the payments function in regulatory examinations and internal/external audits related to instant payments, ACH origination, and third‑party/ISO relationships Participate in industry or regulatory groups, as appropriate 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 Requirements: Education Bachelor's degree in business, finance, or related field, or equivalent professional experience Experience Minimum 7 years in payments or operations at a Bank, Fintech, or complicated payments environment 5+ years of supervisory experience Direct experience in at least one of: ACH origination/TPS programs, merchant acquiring, or commercial/factoring payment flows Demonstrated experience building or substantially redesigning a payments program or product within a regulated financial institution Knowledge, Skills & Abilities Working knowledge of NACHA operating rules, card network rules, and instant payments (RTP/FedNow) operating requirements Accredited ACH Professional (AAP), or ability to obtain within 12-18 months of hire Ability to evaluate and implement payments orchestration or core payments platforms Ability to build and present a business case, including basic P&L and ROI analysis, to executive leadership and/or the Board Strong cross‑functional collaboration skills, particularly with Product Management, Compliance, AML, Fraud, Business Relationship and Operational teams Strong written and verbal communication skills, including comfort presenting to executive leadership, external examiners, and customers. Working understanding of treasury management fundamentals, and how instant payments availability changes liquidity, lending, and working capital needs Preferred Qualifications Prior experience with ISO/merchant acquiring TPS programs or payment facilitator (PayFac) models Experience with factoring, asset-based lending, or commercial finance payment flows Community or mid-size bank experience Additional payments certifications, such as the Accredited Faster Payments Professional (AFPP) and Accredited Payments Risk Professional (APRP) #J-18808-Ljbffr