Head of Telehealth

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 Now

This is a rare opportunity for a technical leader to step into a company with proven revenue, product-market fit, an established team, and a large market opportunity.

Three things make this an inflection point:

1. Product-market fit is established. Demand continues to grow, merchant adoption is accelerating, and Reign is outperforming expectations.

2. There is an opportunity to define a category. While many companies are building AI tools for commerce, few are focused on helping sophisticated DTC operators automate revenue-generating decisions at scale.

3. Our customers are AI-ready. They adopt technology quickly when it drives measurable business outcomes, creating an ideal environment for agentic products.

Why This Role Exists

We found the third of ecommerce that Silicon Valley forgot, and we built the engine that wins it: referrals from merchants who already run on us, and rooms full of the right operators. Now we're bringing that engine to telehealth.

DTC telehealth brands sell the way our merchants sell: paid acquisition, funnels, subscriptions, and a relentless focus on conversion and retention. Weight loss, men's and women's health, hair, skin, hormones, and wellness programs are built by operators who think like direct response merchants. What makes them different is the rulebook. Getting paid in this space depends on certifications, card network registration, pharmacy and provider relationships, and advertising rules, so most commerce platforms can't serve these merchants, and most telehealth brands end up assembling their own stack by hand: a questionnaire tool, a clinical network, a pharmacy, a processor that tolerates them, and a checkout that was never built for them.

A few platforms have started putting the pieces together. Bask Health calls it "telehealth meets ecommerce" and promises a brand launched in days, as simple as setting up a Shopify store. That's the right idea, and it's exactly what Shopify did for ecommerce: make the hard parts easy enough that operators can focus on growth. We intend to do it for telehealth with the commerce engine our merchants already run on: storefronts, checkout, subscriptions, payments, and the CRM. That is the opening. This seat owns it.

Think of it as starting a company inside Reign.com, with you as its CEO. You write the business plan: which segments we go after first and why, what the product and payments setup need to look like, how we price, how we sell, and what it takes to win. You propose the resourcing, and we give you what you need, including the team under you. Then you run it: the design partners, the first merchants, the partners, the product, the numbers. You get more autonomy than any sales or partnerships role here, and the accountability that comes with it.

We are hiring a Head of Telehealth who:

writes the business plan and the go-to-market, and then executes it personally: segments, positioning, pricing, partners, events, and pipeline

lands the design partners who prove the model, and takes them from first conversation to live

turns what you learn in the market into product: the capabilities we have today, the gaps for telehealth, and the things we haven't thought of, built with our product and engineering team

knows what it takes for a telehealth merchant to get approved, stay approved, and scale, and can explain it to a founder and to an underwriter

finds and activates the partners and referral channels that send us telehealth merchants, with a number on each one

tells us what this business needs in people, product, and payments, and makes the case with real merchants behind it

We don't hand you a plan. You bring us one in your first month, with numbers, and then you execute it. The scoreboard is telehealth merchants live on Reign.com and growing, and a business unit that stands on its own.

What You'll Own

The business plan. Who we sell to first and why: which telehealth segments, business models, and merchant sizes we can win today, and which come later. The positioning, the pitch, the pricing, and the product and payments gaps we have to close to win. You put it in writing in your first month, with the resourcing it takes, and you keep it current as the market answers back.

Design partners. The first telehealth brands that build with us. You pick them, you land them, and you take them from first conversation to live and transacting. What they need shapes what we build, and what they prove is what we sell to everyone after them.

The product. We built the engine for DTC merchants. You figure out what it needs to become for telehealth: which of our capabilities already fit, where the gaps are, and what we're not thinking about. You bring what you learn from the market and the design partners to our product and engineering team, and you work with them to build something telehealth operators find compelling, from intake to checkout to refills. You are the voice of the telehealth merchant inside the building, and you own the priorities and the trade-offs for the vertical.

The vertical's number. Telehealth merchants live on Reign.com and transacting. You own the funnel from first conversation to first sale: sourcing, demos, close, and the handoff into underwriting and onboarding, and you stay on every merchant until their first big month. Client success owns the relationship after that.

Approvals. Telehealth merchants can't scale without the right approvals, and neither can we. You know what it takes to get approved and stay approved: certifications such as LegitScript, card network registration and monitoring for healthcare and pharmacy merchants, HIPAA and patient data obligations, provider and pharmacy models including compounding and fulfillment partners, and the advertising standards that affect ad accounts and chargebacks. You counsel merchants on what they need before they reach underwriting, and you help write the standards that keep them approved, practical enough that a merchant can read them and know exactly where they stand. You work with our payments and risk teams on what the vertical needs next.

Partners and referral channels. Telehealth enablement platforms, clinical networks, pharmacies and fulfillment partners, certification firms, agencies, media buyers, and communities. You find the ones that reach our merchants, you make the case, and you get them sending deals. Every partner gets a number, an owner, and a next step.

Market truth. You know the merchants, their funnels, their stacks, and their complaints from memory. You know which platforms and processors they run on today, where we win, and where we don't yet. When a competitor, card network, or regulator makes a material move in telehealth, we know within 48 hours. When our merchants need something from product, payments, or client success, you are the one who says it clearly, with numbers.

What Success Looks Like in 90 Days

Day 30. You know the product the way a merchant does, you've passed the CRM test every new team member passes, and you can demo it to a telehealth founder without notes. You've written the business plan: the segments we go after first and why, the product and payments gaps we have to close, the go-to-market, and the resourcing you need, with numbers. Your design partners are identified, in conversation, and lined up to build with us. You're ready to go.

Day 60. You're executing against your plan. The first design partners are onboarding, the first partner conversations have a number and a next step, and we hear from you every week: what moved, what's blocked, and what you need. The early signs of traction are there, and the plan has already changed because of what you learned.

Day 90. A design partner is live and transacting. The model is working and you can show it: the first merchants, the first revenue, the early signs of product-market fit. You've set the KPIs for the business unit and you report against them every week. Telehealth at Reign.com is rolling, and it's yours to grow.

Who You Are

You live in telehealth. You've spent time selling into, building for, or operating DTC telehealth or digital health businesses. You know the operators, the platforms, the pharmacy and provider partners, and the events.
An entrepreneur at heart. You've started something from zero: a company, a business unit, a vertical, or a market, with no playbook handed to you, and you can show the before and after with numbers. You'd rather write the plan and run it.
A self-starter who finishes. You don't wait for direction, and you don't need much of it. You figure out what the business needs, you go get it, and you see it through. Nobody has to check whether it got done.
You know the rulebook. You understand what it takes for a telehealth merchant to get approved and stay approved, and you can explain it clearly to a founder and to an underwriter.
A closer and a host. You can run a discovery call, demo a product, and close a founder who makes decisions on the call. And you can fill a room with the right people and turn it into pipeline.
Fluent in the merchant's business. Offers, funnels, subscriptions, retention, approval rates, chargebacks, LTV, CAC, and margin. Our merchants can tell within thirty seconds whether you understand their business.
A missile, not a passenger. You operate with a lot of autonomy and solve problems instead of escalating them. You don't bring us problems; you bring solutions and the resources you need to execute.
AI-fluent. You use AI in your work every day: research, prospecting, market mapping, building your playbook. You know where it makes you faster and better, and you'll put the tools the rest of the company already runs on to work from day one.
Startup-forged. You've thrived in fast, resource-constrained, high-intensity environments in the last few years, or you've built something of your own.
No tolerance for mediocrity. The people who 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 sold payments, checkout, or merchant services to telehealth or other high-risk healthcare merchants, and some of them would take your call today.
You've taken a telehealth brand through its approvals yourself: LegitScript, card network registration, or the provider and pharmacy setup.
You've run, marketed, or bought media for a DTC telehealth brand, and you know what a frozen merchant account or a rejected ad account feels like on a Friday night.
You've launched a new vertical or business unit for a company that was new to it, and it's still growing.
You've run a P&L.

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.