Doubtless Pet Insurance is hiring for a Head of Payment Services based in our New York City office

This is a hybrid role with 2-3 days/week in office

Position Overview

The Head of Payment Services leads the global strategy, controls, and day-to-day operations of the merchant acquiring and payment acceptance program, with a primary focus on risk management, portfolio health, operational excellence, and merchant experience. This role owns the end-to-end merchant services lifecycle, including onboarding, operational delivery, ongoing monitoring, disputes and chargebacks, and partner/vendor oversight.

Working closely with Risk, Compliance, Finance, Product, Sales, Relationship Management, and Engineering teams across the global organization, this leader will ensure a compliant, scalable, and high-performing payments program that reduces fraud and losses, maintains card brand and regulatory compliance, improves operational efficiency, and supports retention and profitability.

Key Responsibilities

• Merchant Services Strategy & Leadership — Own the end-to-end merchant services program, including merchant acquisition enablement, onboarding, implementation, administration, and ongoing support. Develop and execute the merchant services strategy and operating plan aligned with company revenue, retention, customer experience, and risk objectives.
• Payment Partner & Vendor Management — Manage strategic relationships with acquiring banks, processors, gateways, and key technology vendors. Negotiate contracts, pricing, service-level agreements, and risk and compliance requirements, including reporting, controls, data handling, and escalation protocols.
• Merchant Onboarding & KYC/KYB — Oversee merchant onboarding and KYC/KYB processes in partnership with Risk and Compliance, ensuring policy adherence, appropriate exception handling, and documentation standards aligned with card brand requirements and internal controls.
• Portfolio Risk Governance — Establish and operate a comprehensive portfolio risk governance program, including risk appetite, monitoring rules, merchant reviews, and control implementation. Proactively identify emerging risks, enforce appropriate controls, and maintain a healthy merchant portfolio.
• Fraud, Disputes & Chargeback Management — Own the fraud and chargeback operations strategy in partnership with Fraud and Risk teams, including monitoring, alerts, reserves and holds where applicable, dispute workflows, representment strategy, and continuous improvement initiatives designed to reduce losses and operational burden.
• Operational Risk & Controls — Maintain a strong control environment through documented policies and procedures, appropriate segregation of duties, periodic control testing and quality assurance, vendor oversight, business continuity readiness, and support for internal and external audits, card brand reviews, and partner examinations.
• Payment Operations — Drive operational excellence across settlement and funding, reconciliation, chargebacks and representment, disputes, and merchant account maintenance. Establish clear service levels, controls, quality standards, and accountability across payment operations.
• Incident & Escalation Management — Lead the response to payment and merchant risk events, including fraud spikes, compliance breaches, and funding or settlement issues. Oversee containment, stakeholder communications, root-cause analysis, corrective action plans, and resolution of high-impact merchant issues.
• Portfolio Performance & Profitability — Monitor and improve key portfolio metrics, including approval rates, activation, processing volume, attrition, fraud and chargeback performance, reserve exposure, and net revenue yield. Identify opportunities to improve profitability through pricing, fees, authorization performance, and operational cost-to-serve while maintaining appropriate risk standards.
• Reporting & Risk Analytics — Establish and maintain operational and risk dashboards, early-warning indicators, trend reporting, and exception monitoring. Provide leadership with regular visibility into portfolio performance, losses, compliance posture, emerging risks, and remediation progress.
• Technology & Process Improvement — Partner with Product and Engineering to strengthen operational resilience and payment risk capabilities, including monitoring, rules engines, case management, reporting, and reconciliation automation. Prioritize roadmap enhancements that reduce loss, improve efficiency, and minimize merchant friction.
• Commercial & Cross-Functional Partnership — Partner with Sales and Relationship Management teams to operationalize merchant offers and ensure proposed deals are supportable, compliant, and within established risk appetite. Serve as a senior escalation point for complex merchant accounts and payment-related issues.
• PCI & Compliance Oversight — Manage approved PCI auditor relationships and associated compliance reporting requirements.

Qualifications

• Bachelor’s degree in Business, Finance, Operations, or a related field, or equivalent practical experience.
• 8+ years of experience in large corporate merchant services, acquiring, fintech, payments, or related financial services roles.
• Demonstrated experience managing payment partners and vendors, including processors, gateways, orchestrators, and acquiring banks, with experience negotiating commercial terms.
• Strong working knowledge of card brand rules, chargebacks and disputes, fraud and loss concepts, settlement and funding, and reconciliation processes.
• Experience designing and operating controls, policies, procedures, and monitoring programs within a regulated environment.
• Experience supporting audits, regulatory or partner examinations, and compliance reviews.
• Strong analytical and financial acumen, with the ability to understand and manage key P&L drivers including processing volume, yield, pricing, and cost-to-serve.
• Excellent stakeholder management and communication skills, with demonstrated ability to influence and partner effectively across Sales, Product, Risk, Compliance, Finance, and other functions.

What Success Looks Like

• A scalable, well-controlled merchant services program that supports company growth while maintaining disciplined risk standards.
• Strong portfolio health, with effective early identification and mitigation of fraud, chargeback, compliance, and merchant risks.
• Efficient, reliable payment operations with clear controls, service levels, and accountability across settlement, reconciliation, disputes, and merchant servicing.
• Productive and commercially sound relationships with acquiring banks, processors, gateways, and other critical payment partners.
• Measurable improvement in operational efficiency, loss performance, merchant experience, retention, and portfolio profitability.
• Strong cross-functional partnership that enables the organization to pursue growth opportunities without compromising compliance, operational integrity, or established risk appetite.

All of our jobs come with great benefits including healthcare, parental leave and opportunities for career advancements. Some offerings are dependent upon the location of where you work and can include the following:

• Comprehensive full medical, dental and vision Insurance

• Basic Life Insurance at no cost to the employee

• Company paid short-term and long-term disability

• 12 weeks of 100% paid Parental Leave

• Health Savings Account (HSA)

• Flexible Spending Accounts (FSA)

• Retirement savings plan

• Personal Paid Time Off

• Paid holidays and company-wide Wellness Day off

• Paid time off to volunteer at nonprofit organizations

• Pet friendly office environment

• Commuter Benefits

• Group Pet Insurance

• On the job training and skills development

• Employee Assistance Program (EAP)