Chief Payments Officer

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.

$1B+ in GMV in under 3 years of operating

8-figure ARR, growing 100%+ YoY (top 0.5% of all startups launched in 2024), and we do it with capital efficiency: there is a real chance we finish the year with more cash on our balance sheet than we have ever raised

Rapid merchant adoption and expanding market presence

On track to beat our budgeted sales target by 100%+

Industry-leading NPS score

70% of our new deals come as referrals from existing merchants

Industry-leading AI-native engineering: our engineers ship with agents every day, some of our best builders are non-technical, we ship 17x faster than we did in January, and our software development cycle benchmarks in the top 10% of the industry

Venture-backed by a multi-billionaire ex-founder and direct response industry leaders

An executive team that has done this before: multiple leaders who have scaled a company from zero to unicorn status

A founder who builds from domain expertise: he bootstrapped $200M+ in DTC revenue as a direct response merchant before starting Reign.com, and is building the platform he always wanted as a merchant

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.

Our merchants are the ones Shopify Payments turns away: direct sale dropshippers, auto-ship supplement brands, and subscription businesses with higher chargeback risk and continuity billing. They can't grow without processing, and most of them have spent years stitching it together by hand: a few high-risk MIDs from ISOs that take a week to answer, a PayFac account that could close on them any morning, and nobody who can tell them what to do next.

Reign Payments is our answer: one application, same-day activation, and a home for every kind of transaction a merchant runs, with low-risk rails and high-risk acquirers behind one portal.

High-risk payments hasn't seen real innovation in over a decade, and we behave like a Silicon Valley technology company. We own the storefront and the checkout, so we have maximum visibility into every merchant: real orders, tracking numbers, refunds, and chargebacks, as they happen. No ISO has that. And we run it AI-native. AI agents watch the whole book and flag risk before it becomes a problem, and they're taking over the underwriting checks that used to need a room full of people. We have the strongest engineering team in direct response, and we ship at the speed of light thanks to our investments in our AI SDLC. You tell us what payments needs and we'll build it with record pace.

Payments is already a significant part of our revenue, and we think it becomes most of it.

The questions that decide how big it gets are still open. Should Reign.com be a merchant of record, a registered ISO, a sub-ISO with better economics, or a different answer for each kind of merchant? Which acquirers, sponsor banks, and PayFacs do we build the next five years on, and on what terms? How small and how automated can the team behind it be? Today our founder and our President work those questions between everything else they do. They need an owner who thinks about nothing else.

Think of it as running a company inside Reign.com, with you as its CEO. The strategy, the partners, the P&L, the risk appetite, and the team are yours. You tell us what the business needs in capital, people, and product, and we back you.

And you don't have to worry about GTM. Our software sales team already brings the merchants in. We're signing new merchants at a record pace, most of them come to us as referrals from merchants already on the platform, and every one of them needs processing. You get a founder's autonomy with the demand, the product, and the engineering team already behind you.

We are hiring a Chief Payments Officer who:

charts how we monetize payments, with the math behind each path, and then gets us there

builds and owns the relationships with the acquirers, banks, ISOs, and PayFacs we run on

runs payments as a P&L: take rate, margin, losses, and how much of our merchants' volume runs on Reign Payments

holds a lean team to a hard standard, where every function has an owner and every owner has a number

builds the operation AI-native, so volume can double without the team doubling

knows the high-risk game from the inside: chargebacks, continuity, MID strategy, and what a bank will and won't tolerate

The payments strategy. How Reign.com makes the most money on every dollar of GMV, and what we have to become to do it: merchant of record, registered ISO, sub-ISO, PayFac partner, our own BIN, or a mix by merchant type. You put the answer in writing in your first 30 days, with the unit economics of each path, what it takes in capital, liability, and compliance, and the order we do it in. Then you run it, and you keep a three-year view current as the card networks, the banks, and our book change.

The partners. Acquirers, sponsor banks, ISOs, PayFacs, gateways, and the alert and dispute vendors. You know the decision-makers personally and you negotiate the buy rates, the reserves, and the terms yourself. The partners we build on activate merchants the same day, pay us what the volume is worth, and integrate by API. We run enough of them that no single partner can put a merchant's business at risk.

The P&L. Take rate, processing margin, pricing, reserves, and losses, plus the share of our merchants' volume that runs on Reign Payments. You price merchants to their risk, you can rebuild our take rate from interchange up, and you forecast it with our CFO. When a basis point leaks, you know where it went.

The book. Our risk appetite, our underwriting standards, and how we monitor merchants after they're live. You keep our ratios inside what the card networks and our partners allow, you grow the low-risk side of the book alongside the high-risk side, and you make the call when a merchant has to be capped or cut. Our merchants run hot by the standards of a low-risk processor, and the job is keeping the good ones processing. You coach them on MIDs, descriptors, billing, and alerts before a ratio becomes a problem.

The team. Underwriting, risk, and payments operations report to you. In your first month you map every function in the department: who owns it, what their KPI is, and how we measure it. From there the team is the size the work calls for. Coach fast, decide fast.

The AI-native operation. Our AI agents already flag shipping, reputation, and chargeback problems across the book every night, and we're building the ones that read applications, check documents and websites, and match each merchant to the right bank. You work with our VP of Payments Automation to make sure we run payments AI-native, and scale to billions in GMV without the typical headcount.

Merchants and the product. Our biggest merchants want a sharp thought partner on payments who understands their game: MID strategy, approval rates, routing, and what to do before peak season. That's you. You are also the voice of payments inside the building: you tell product and engineering what Reign Payments needs next, with the revenue behind each ask.

Day 30. You know the book from memory: our top merchants by volume, every partner and what we earn on each, our ratios by rail, and where we make and lose money. You've met every person on the team, and the map of the department is written: each function, its owner, its KPI. Your payments strategy is in writing, with numbers, and you've made the case for it to the CEO and the President. And you've made the key payments partnerships that strategy runs on.

Day 60. You're executing your plan. The team is the size and shape the work calls for, and every person on it can tell you their number. Merchants are processing on the partnerships you made in your first month. We hear from you every week: what moved, what's blocked, and what you need.

Day 90. The plan is showing up in the numbers: take rate, the share of volume on Reign Payments, and time to activation. Our partners know you as the person at Reign.com who decides. Our President will tell you payments stopped being his second job. The business unit keeps kicking out cash as we scale GMV, without operational noise or disorder. You've set the KPIs for the next twelve months and you report against them every week.

An entrepreneur who has run payments as a business. You've been a founder, a GM, or the #1 or #2 at an ISO, a PayFac, a merchant of record, or a platform where payments was the main revenue line. You've owned the P&L, and you can show the before and after with numbers.

You've done the math on the structures. Merchant of record, registered ISO, sub-ISO, PayFac: you've operated inside more than one, you know what each earns and what each puts at risk, and you have an opinion on which fits a book like ours. We expect you to teach us things we don't know.

High-risk is home. You've lived card-not-present books with high chargeback ratios: direct response, nutra, continuity and subscription billing, the merchants Shopify Payments won't keep. You know the monitoring programs, MID strategy, reserves, and what an acquirer will and won't tolerate, because you've been in the room when it went wrong. And you like merchants: you look for the way to keep a good one processing before you look for the reason to shut them off.

The banks and ISOs take your call. You have real relationships with acquirers, sponsor banks, and processors, you've negotiated the agreements yourself, and the partners you've worked with would work with you again.

A drill sergeant with no ego. You hold a hard bar every day, you give direct feedback, and you address underperformance early. You've restructured a team and it got better. You admit your own mistakes fast.

In the weeds by choice. You read the chargeback report yourself, you know which MID is running hot before your team tells you, and you'd rather pull the data than wait for a deck. A payments executive who "stays above the details" makes you uncomfortable.

AI-native in how you run a team. You use AI in your own work every day. When a process breaks, your first question is what an AI agent can do. Adding headcount is your last answer.

A missile, not a passenger. You are an entrepreneur at heart who operates with a lot of autonomy and solves problems instead of escalating them. You don't bring us problems; you bring solutions and the resources you need to execute.

Startup-forged. You have thrived in fast, resource-constrained, high-intensity environments in the last 5 years.

No tolerance for mediocrity. The individuals that thrive here hold themselves and others to an extremely high standard with no exceptions. We're here to build a generational company.

Huge Plus

You've founded a payments company, or been the first payments hire at a platform and built the function from zero.

You've taken a company through ISO registration, a sponsor bank relationship, a PayFac build, or getting its own BIN.

You've grown the low-risk side of a high-risk book, through sales, partnerships, or acquisition.

You've run or marketed a direct response brand yourself, and you know what a frozen MID feels like on a Friday night.

You've built AI agents that have automated key workstreams.

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.