Vice President of Payments (High-Risk)

Reign is the Autonomous Commerce Platform for DTC founders. We unify storefronts, checkout, payments, and operations into one AI-native platform where agents handle the operational grind and merchants focus on growth: making the most money, with the least headache, on their own terms.

We set out to build the "Shopify of Direct Response," and along the way recognized something bigger. Direct response represents roughly a third of all ecommerce transactions, a trillion-dollar market chronically overlooked by Silicon Valley. The merchants who run it are obsessive about tooling. They live and die by velocity, conversion, and margin. Without traditional brand moats, they compete on operational excellence, making them some of the earliest and fastest adopters of AI agents in commerce.

This is a category-defining opportunity, and we're pursuing it from a position of strength.

• 8-figure ARR, growing 100%+ YoY, with exceptional capital efficiency and strong unit economics.

• Rapid merchant adoption and expanding market presence, on track to exceed our budgeted sales target by more than 100%.

• Industry-leading customer satisfaction, with 70% of new deals coming from referrals by existing merchants.

• Venture-backed by a multi-billionaire former founder and leaders in the direct response industry.

• Experienced executive leadership, including multiple leaders who have helped scale companies from zero to unicorn status.

• Built by a founder who knows the industry firsthand, having bootstrapped more than $200M in DTC revenue as a direct response merchant before founding Reign.

This is a rare opportunity for a payments leader to join a company with proven revenue, established product-market fit, an experienced team, and a significant market opportunity.

Three things make this an inflection point:

1. Product-market fit is established. Merchant adoption is accelerating, referral-driven growth is strong, and Reign continues to outperform expectations.

2. Payments is central to our growth strategy. As merchant volume scales, there is an opportunity to build a differentiated high-risk payments business that balances growth, profitability, and disciplined risk management.

3. Our customers are AI-ready. They adopt technology quickly when it delivers measurable business outcomes, creating an ideal environment for intelligent payments infrastructure, automation, and operational efficiency.

We are hiring a Vice President of Payments (High-Risk) to lead Reign's high-risk payments business end to end, owning the P&L, risk strategy, bank and processor relationships, and the operational infrastructure supporting merchant growth.

This is the most senior payments leadership role at Reign. You will oversee underwriting, risk, payment operations, partner strategy, and payments go-to-market strategy across both revenue and product. The Director of Payments Risk, along with the underwriting and risk teams, will report into this role.

Reign serves direct response ecommerce merchants across nutraceuticals, supplements, skincare, clothing, accessories, and subscription and continuity offers. Operating successfully in these verticals requires exceptional judgment, disciplined monitoring, and strong acquiring bank relationships.

We are looking for an experienced payments executive who understands high-risk merchant acquiring firsthand. You should have navigated card network monitoring programs, defended merchant portfolios with acquiring partners, structured complex merchant relationships, and made difficult risk decisions while protecting profitability and processing continuity.

This is a hands-on executive leadership opportunity for someone who can balance commercial growth with sophisticated risk management, build scalable operations, and help establish payments as a competitive advantage for Reign.

Payments P&L & Commercial Strategy

Own the revenue, cost structure, profitability, and overall financial performance of Reign's high-risk payments business. Develop the commercial strategy, including ideal customer profiles, pricing, and portfolio economics, while partnering closely with Sales on go-to-market execution.

• Own processing revenue, interchange economics, net effective rates, and contribution margins.

• Establish merchant pricing strategies, pricing governance, and profitability targets.

• Manage residual and revenue-sharing economics with ISOs, agents, and referral partners.

• Optimize processing costs, gateway fees, vendor expenses, and partner economics.

• Oversee loss reserves, write-offs, and net risk costs.

• Drive profitability across individual merchants, verticals, and portfolio segments.

• Build financial forecasting, reporting, and dashboards that provide clear visibility into revenue, risk exposure, and margin.

Risk Management & Underwriting

Define and own Reign's risk appetite, underwriting strategy, and portfolio risk management framework, ensuring sustainable growth across high-risk merchant verticals.

• Establish underwriting policies, approval authorities, and escalation thresholds.

• Develop reserve strategies, rolling holds, processing limits, and risk-adjusted merchant terms.

• Manage portfolio concentration across merchant verticals, acquiring banks, and processors.

• Own chargeback and fraud monitoring thresholds, remediation strategies, and escalation procedures.

• Lead ongoing portfolio monitoring, periodic merchant reviews, and offboarding decisions.

• Partner with Sales and Client Success on sensitive merchant communications and risk-related decisions.

• Maintain compliance with Visa and Mastercard monitoring programs, including VAMP, VDMP, VFMP, and MATCH/TMF requirements, while supporting continued processing volume growth.

Banking, Processor & Partner Strategy

Own and expand the strategic relationships that enable Reign to underwrite, board, and process payments for high-risk merchants.

• Build, maintain, and negotiate relationships with sponsor banks, acquiring banks, processors, and payment gateways.

• Develop diversified banking and processing partnerships to reduce concentration risk and ensure business continuity.

• Negotiate Schedule A agreements, buy rates, commercial terms, and processing economics.

• Lead bank audits, ISO/MSP registration requirements, and ongoing partner compliance reporting.

• Manage escalations, remediation efforts, and portfolio reviews with acquiring partners.

• Identify and execute opportunities to expand into new merchant verticals, markets, and geographies.

Payment Operations & Infrastructure

Lead the operational infrastructure supporting Reign's payments business, ensuring accuracy, scalability, efficiency, and a strong merchant experience.

• Oversee merchant onboarding, KYC/KYB, activation, and time-to-board.

• Own funding, settlement, reconciliation, and residual accuracy.

• Manage chargeback prevention and mitigation capabilities, including Ethoca, Verifi, VMPI, RDR, and CDRN.

• Improve authorization performance, decline recovery, and payment routing.

• Establish scalable operating procedures, SLAs, performance dashboards, and accountability systems.

• Identify opportunities to automate workflows, reduce manual processes, and improve operational efficiency through AI-native tools and systems.

Payments Growth & Product Strategy

Position payments as a strategic growth engine for Reign, driving merchant success, revenue expansion, and competitive differentiation.

• Improve authorization and approval rates to increase merchant conversion and processing volume.

• Drive adoption and attach rates of Reign's payments solutions across the merchant base.

• Partner with Product and Engineering to shape the payments roadmap based on merchant needs and commercial opportunities.

• Develop pricing and packaging strategies that improve both merchant economics and Reign's contribution margins.

• Evaluate new payment methods and rails, including ACH, RTP, and alternative payment methods.

• Identify opportunities to expand payments monetization and create additional revenue streams.

Team Leadership & Executive Partnership

Build and lead a high-performing payments organization while serving as Reign's senior executive voice on payments strategy, risk, and operations.

• Lead, develop, and scale teams across underwriting, merchant risk, and payment operations.

• Establish clear performance expectations, operating metrics, and accountability frameworks.

• Recruit and retain exceptional talent while fostering a culture of precision, urgency, ownership, and sound judgment.

• Partner closely with the CEO, Finance, Product, Sales, and Client Success to align payments strategy with company objectives.

• Represent Reign in strategic discussions with acquiring banks, processors, investors, and the Board.

• Balance aggressive commercial growth with disciplined risk management, operational resilience, and long-term portfolio profitability.

Required Qualifications

• 8+ years of experience in payments, merchant acquiring, or fintech, including at least 5 years directly managing high-risk merchant portfolios.

• Proven experience owning a payments P&L, merchant portfolio, or business unit, with direct accountability for revenue, profitability, and risk performance.

• Deep expertise in high-risk ecommerce and card-not-present acquiring, including direct response, nutraceuticals, supplements, skincare, and subscription or continuity billing models.

• Hands-on experience operating within ISO, MSP, PayFac, or sponsor bank models.

• Established relationships with acquiring banks, sponsor banks, processors, and payment gateways.

• Demonstrated expertise in Visa and Mastercard monitoring programs, including VAMP, VDMP, VFMP, and MATCH/TMF, with experience navigating escalations and remediation.

• Proven ability to develop and execute underwriting policies, reserve strategies, rolling holds, processing limits, and portfolio risk frameworks.

• Track record of managing chargeback and fraud exposure while growing processing volume and maintaining profitable merchant relationships.

• Strong command of KYC/AML, PCI DSS, NACHA, and applicable card network regulations.

• Experience negotiating acquiring agreements, processing economics, and commercial terms with banking and processing partners.

• Demonstrated success building, leading, and developing teams across underwriting, merchant risk, and payment operations.

• Strong financial and analytical capabilities, including experience managing portfolio economics, merchant profitability, forecasting, and performance reporting.

• Ability to make fast, independent, defensible decisions in complex, high-pressure environments.

• Executive-level communication skills, with the ability to represent the payments business to senior leadership, banking partners, and external stakeholders.

Preferred Qualifications

• Leadership experience at a high-risk ISO, PayFac, merchant acquirer, or payments-enabled ecommerce platform.

• Experience establishing new acquiring bank or processor relationships from the ground up.

• Proven success navigating card network monitoring programs, bank remediation, or portfolio recovery initiatives.

• Experience with embedded payments, ISV platforms, or payments monetization strategies.

• Familiarity with direct response, DTC ecommerce, and recurring-revenue merchant models.

• Experience driving authorization optimization, payment routing, and merchant conversion improvements.

• Exposure to ACH, RTP, and alternative payment methods.

• Experience leveraging automation, AI, or data-driven tools to improve underwriting, monitoring, and payment operations.

• Experience operating in a fast-paced startup or high-growth environment with significant ownership and accountability.

• Bachelor's degree in Business, Finance, or a related field.

We are a value-driven company. These aren't words that we just put on a wall. They dictate how we hire, fire, and promote.

All In to Win. Operate with urgency and a relentless focus on excellence.

A Players Only. Build and maintain exceptional talent density. Pure meritocracy.

Merchant First. Every decision is measured by merchant impact.

Entrepreneurial Spirit. Move quickly, stay resourceful, and take ownership.

No Ego. The best ideas win regardless of title or tenure. No BS politics.

**Reign is mission-first and performance-driven. We operate with urgency, give direct feedback, and expect high ownership. If you thrive under pressure and love building in fast-moving environments, you'll do great here. If you strongly prioritize predictability, comfort, and work/life separation, this 100% isn't the right role.**

We operate as a flat, high talent density, meritocratic organization.