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Head of Product / VP of Product

ReignProduct
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United States
Work type
Remote
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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 we recognized something bigger. Direct response is 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. They have no brand moats, so they compete purely on operations, which is exactly what makes them the earliest and fastest adopters of AI agents in commerce.

This is a category-defining bet, and we are running at it from a position of strength.

Where We Are Today

  • 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
  • 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, and is building the platform he always wanted as a merchant

    • Why This Role Exists

    We found the third of ecommerce that Silicon Valley forgot, and by the end of this year we expect to have out-shipped the legacy players who coasted on it for a decade. That is the next twelve months. The five-year bet is bigger: commerce where agents run the operation and the founder makes the calls that matter, built by a company that already runs itself that way. Our engineers ship with agents every day, two of our most productive builders are non-technical, and our CEO ships his own PRs.

    Today product direction comes from two people: our Founder, who ran $200M+ of DTC revenue before he started this company, and his CoFounder with the sharpest short-horizon product instincts in in team, who hears a merchant's problem and ships the fix the same week. This week's and this month's calls are good. Past that, the ball drops. An organization needs to plan, and nobody owns the plan: the two-quarter roadmap, the written case for the next three years. Nobody owns the outside world as a job: our top merchants' funnels, our vendors' roadmaps, our competitors' releases, the markets we have not entered. And nobody owns the product organization: who we hire, the bar they are held to, and if we need to / how we need to grow this function as we scale.

    The job is a grind by design: living in the CRM daily, testing Reign AI the way a merchant would, answering an engineer's question about moving subscriptions from one gateway to another within the hour, knowing our top 25 merchants' funnels cold, and shipping the fix yourself when the merchant on the call needs it this week. It is also a seat at the table. Our founder and CEO wants a product leader who can sit across from him and the CTO and argue about where the next three years go, with the credibility that comes from knowing the product, the merchants, the market, and the build better than anyone else in the room.

    Staying close to the realities on the ground is not a stage we are passing through. It is how our entire leadership team operates today, and it is how we intend to operate for the rest of this company's history. We are allergic to ivory towers.

    This is not a "set the vision and delegate" role. We are hiring a VP of Product who:

  • knows our product, our competitors, our merchants, and our vendors inside and out, because you talk to them every week, and has the taste and judgment to know what to build because you did the homework first
  • builds. You ship through our AI SDLC yourself, so your calls come from having built the thing, and the builders here respect them for it
  • runs the roadmap as a living set of bets, not a document. Every item has an ROI case, a reason it sits where it sits, and a trade-off the team understands
  • is a real thinking partner to the CEO and the CTO on where Reign.com places its next bets, and writes the case before the decision
  • holds the bar for PMs and engineers, as a drill sergeant when needed, and has the hard conversations personally

    • How this fits with the exec team. You report to the CEO. The CTO owns technical vision, tempo, and the engineering organization; you are the CTO's peer on what gets built and why, and the two of you run product and product engineering as one motion. One product organization, one roadmap.

    What You'll Own

    Product strategy, with the CEO and the CTO. The next three years in writing: which bets, in what order, what we build, buy, or partner for, which markets we enter and when, and what we stop doing. You bring the outside-in case from merchants, competitors, vendors, and markets, and the inside-out case from what the team can build and by when. The CEO and the CTO argue with you, the decision gets written down with its reasoning, and when the CEO is about to make a product call, he wants your memo first.

    The roadmap past the month. The two-quarter roadmap and the twelve-month plan, run as a living set of bets. Every item has an ROI case, a reason it sits where it sits, and a trade-off the team understands. Every card has a date, slips are visible before anyone asks, and you have a sniff for wasted engineering hours. You and the CTO move product and engineering as one motion, specs before delivery. You kill work that doesn't earn its place, and you say so out loud.

    Merchants, vendors, and markets. Direct relationships with our top merchants: you sit in their channels, you are on calls weekly, you know their funnels and complaints from memory, and repeat pain points become shipped fixes in weeks, not quarters. Merchants want to talk to you because you know their business and our product cold. You are the product owner of our relationships with the processors, payment methods, platforms, and AI vendors our product depends on: you know their roadmaps and their gaps, you make the build, buy, or partner call, and no integration's scope lives in one person's head. And you own the market view: where the next cohort of merchants is and what would make them move, in writing every quarter.

    Competitors and the scoreboard. Objectively measurable superiority against our direct competitors: revenue per visitor, checkout conversion, page speed, approval rate, activation, retention, and user experience, benchmarked consistently. You have accounts on every competitor's product and you actually use them, so you know exactly where we are better and where we are not. When a competitor or a major platform ships something material, our response memo exists within 48 hours. A/B tests with real sample sizes, and the honesty to know when we are winning versus when merchant behavior is flattering us.

    Building. You ship: the prototype before the spec, the fix you heard on a merchant call, the internal tool the leadership team needs by Friday. Through the same system our engineers and our non-technical builders use: Claude Code, agents, MCP, and our own APIs, with tests before the code, an independent verifier on every PR, and a human on every merge. Your specs read like the merchant wrote them, and an agent can build from them without a meeting. When you tell an engineer a feature should take a week, it is because you built the first version yourself.

    The product, and the bar for shipped. Storefronts, checkout, payments, the merchant OS, and Reign AI, our merchant-facing agent. Specs, quality, and rollout, and a much higher bar for the word "shipped." A feature flag is not shipped. An announcement is not shipped. Shipped means merchants found it, adopted it, and would be annoyed if we took it away. It means the execution was elegant, the business problem it was built for is gone, and we can draw a straight line from it to Reign.com making more money or a merchant growing faster. Anything short of that is still in progress, and you are the person who refuses to call it done. For Reign AI the bar is higher still: merchants rely on it for decisions on real revenue, so you test it the way a merchant would, you define what "good" means, and you hold the line.

    The product organization. A small team of PMs who build. You hire them for taste and judgment, and you set the standard for what a Reign.com PM ships: PRDs with prototypes, specs with test cases, launches with reference merchants and KPIs, and PRs of their own through our AI SDLC. Coach fast, decide fast. You give tactical, in-depth feedback on every spec, prototype, and PR that matters. And you handle the hard parts yourself: when someone is not going to make it, you have the conversation early and in person, with a transition map, so no merchant, partner, or engineer learns about it from a gap.

    What Success Looks Like in 90 Days

    Day 30. You are a power user of the entire platform, and you have shipped through our AI SDLC in your first week and every week since, with a PR in production that a merchant or a teammate uses. You know our top 25 merchants by GMV, their funnels, and their top requests from memory, and you have been on calls with ten of them and with our five most important vendors and partners. You have shipped a written competitive teardown covering where we win and where we are behind, you have assessed the PM team, and you can say why every roadmap item sits where it sits.

    Day 60. You own the roadmap and its sequencing for the next two quarters, in writing the whole company reads. You have killed at least one item that no longer earns its place and said so out loud, and you have made one build, buy, or partner call with a written case behind it. You can tell the leadership team things about our competitors and our market that we do not know on our own. Every card has a date. Engineers say your PMs' specs are clearer than what they would write themselves, our product lead says you made him faster, and executives say they are making better bets because of your work.

    Day 90. At least one scoreboard metric has moved because of work you sequenced. The three-year product strategy exists in writing and the CEO and the CTO are making bets from it. When a competitor or a platform moved this quarter, your memo was in their inbox within 48 hours. Our top merchants can name something that got better because you showed up, and at least one vendor relationship has turned into something merchants use. The PM bar is visibly higher, engineering says product makes them faster, not slower, and the CEO wants your research before he makes the call.

    Who You Are

  • A builder, not a coordinator. You have been the #1 or #2 product leader at a growth-stage company, you have owned a product surface where conversion, latency, and reliability carried direct economic consequences for your customers, and you have taken a product from behind a competitor to ahead on a measurable metric. You can show the before and after.
  • You ship with agents. You prototype before you spec and you build through agents every day, with tests and a verifier, to production. You can name the last three things you shipped with an agent, who used them, and what they replaced, and you can show one live. You have shipped AI into production with real opinions on determinism, evaluations, and building reliably on non-deterministic layers. Our best builders will know within an hour of pairing with you whether you are one of them. If your instinct when you see a problem is to write a brief for someone else to build, this is the wrong seat.
  • Taste and judgment. You know what a feature is supposed to do before anyone writes a spec, and you know what makes it look sexy to the merchant using it. You do the homework first: what the merchant actually asked for, what the competitors already solved, what the numbers say. You have shipped things people chose to use, and killed things that would have shipped on time and changed nothing.
  • Technical enough to be dangerous. You read PRs, you can follow a gateway migration or understand why a cron job is locking a table, and you hold your own in an architecture conversation with the CTO.
  • Outside-in, in writing. You have carried a product company's relationships with its biggest customers and the vendors it depended on yourself. Customers take your call because you know their business; vendors take it because you know their roadmap. You come back from an industry event, a partner's office, or a competitor's demo with a written view of what it means for us, and you have had a founder and a CTO argue with your strategy memo until they changed their minds or you changed yours.
  • In the weeds by choice. You use the product every day, you would rather test a flow yourself than read a report about it, and you see the bug before the customer reports it. A product leader who "stays above the details" makes you uncomfortable.
  • A drill sergeant with no ego. You give very tactical, in-depth feedback on the work PMs and engineers are actually doing. You hold the bar, address underperformance early, have the hard conversation yourself, tell people directly, and admit your own mistakes fast.
  • 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, at a company that already builds with agents or on your own. If your last five years were spent running product at a company that had already won, this will feel like a different sport.
  • 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.

    • Our Stack

    A TypeScript monorepo (NestJS, Node, pnpm) and a React portal. MySQL, Redis, and ClickHouse Cloud. AWS EKS with per-PR sandboxes, GitHub Actions, Datadog and OpenTelemetry. For the agent: the Anthropic SDK, our own MCP server, and Langfuse for traces. For building: Claude Code with tiered models, a multi-agent pipeline that plans, builds, reviews, and verifies, a headless browser harness with hundreds of saved screenshot scenarios, and a team brain that hands work between people and their agents. Claude Code is a real part of the daily workflow here, not a garnish.

    Huge Plus

  • Ecommerce, direct response, or high-risk payments experience. You have built checkout, subscription billing, or payments products for merchants, or you have worked inside a company in our competitive set.
  • You have run a DTC or direct response store yourself and know what a broken checkout feels like on a Friday night.
  • You have sat on the product side of a partnership with a payment processor, a commerce platform, or an app marketplace, and you know how a partnership turns into a roadmap.
  • You have shipped an AI agent or LLM-powered feature that customers rely on in production, with evals and traces.
  • You have founded a company, or been an early operator who owned the outcome.

    • Our Values

    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.

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