Head of Strategic Sales

About the role

Reports to: CEO

Location: Remote (US) or Burlington, VT (hybrid)

Why this role exists

OhMD is patient communication software for physician practices. Two-way texting, digital forms, automated workflows - and OhMD AI, our AI voice agent. It picks up on the first ring, handles the routine calls a front desk shouldn't have to take, and hands the conversation to a human the second it needs one, with full context attached.

We've spent years making OhMD AI work inside the messiest systems in healthcare.

Multi-site groups, MSOs, and large specialty practices have exactly the problem we solve, multiplied across every location they run. Our customers are buying a front desk that stops turning over, a schedule that stays full, and a patient who doesn't leave for the practice down the road.

You'll carry your own number against the largest accounts we go after, and you'll raise the level of how the account executives beside you sell.

The best version of this person has founded something, or has run a territory as if they had. Builds pipeline from nothing. Someone who builds relationships and is an exceptional listener. Someone who builds trust through value. If that's you, we'd like to talk.

What your first 90 days look like

Weeks 1-4: Learn the product cold. Sit on go-lives. Listen to real calls OhMD AI handles. Shadow every live deal the AEs are running. Talk to ten customers about why they bought and what changed after. Build your target account list.

Weeks 5-8: Pipeline built and moving. First strategic opportunities in discovery. Running weekly deal reviews with the AEs. Rewriting how we do discovery and demo so it starts with the buyer's pain and ends with a number.

Weeks 9-12: First strategic deal closed or on a clear path. A forecast the CEO can trust. A point of view on what's broken in our sales motion and what you're changing first.

Essential Duties - What You'll Own

• Strategic new logo.
• Multi-site groups, MSOs, and large specialty practices.
• Deals of $100K+ ACV on three-to-six-month cycles, signed by a COO, CIO, or CEO.
• You source the pipeline yourself.
• You multi-thread the account, run the evaluation, bring in the right people at the right moment, negotiate, and close.

• Expansion.
• Customers with more locations, more service lines, or OhMD AI not yet turned on.
• You know the base, find the whitespace, and build the case for the next phase in the CEO's language.

• Selling value, not features.
• Discovery that gets to the real cost of the problem: hold times, abandoned calls, front-desk turnover, no-shows, patients who leave.
• A proposal that puts a dollar figure on it.
• A demo you run yourself, built around their workflow instead of our menu.
• A story the buyer repeats internally without you in the room.

• Coaching AEs.
• A small team of account executives, and their number is part of yours.
• Weekly deal reviews.
• Call reviews.
• Joint calls on the ones that matter.
• Cadence discipline, follow-up that doesn't quit, and closing.
• You set the standard by doing it, then hold the team to it.

• Building the motion while running it.
• Account plans, sequences, mutual action plans, a forecast that means something.
• What works for you becomes how we sell.
• You write it down, and the team adopts it.

• Being the voice of the market.
• What you hear from COOs and CIOs goes straight to product and marketing.
• The objections, the competitors in the room, the words buyers use.
• You're the shortest path from the market to the roadmap.

Non-Essential Duties

• Representing OhMD externally. Industry conferences and partner events, including our EHR partners, where the audience is the people you sell to.
• Helping build the sales team. As the motion proves out, you'll shape what the next sales hires look like and sit in on those interviews.
• Other duties as assigned.

Qualifications

Required

• 5+ years selling B2B software, with 3+ years closing $100K+ ACV deals to executive buyers.
• Healthcare software, sold into physician practices, multi-site groups, MSOs, or the ambulatory side of health systems.
• You know what a practice administrator's day looks like and what a COO's board deck looks like.

• A track record you can show us.
• Your quota attainment for the last three years.
• The biggest deal you closed and how it happened, start to finish.
• Consistent top-of-stack performance, not one good year.

• Founder energy.
• You've started something, or you've run a territory like you owned it.
• You build pipeline from nothing, you don't wait for marketing, and you're comfortable being the reason a deal exists.

• Value selling, proven.
• You can describe a deal where you changed what the buyer thought they were buying.
• You run discovery that finds cost, not pain points on a slide.
• Familiarity with MEDDIC, Challenger, or similar is expected; evidence you've done it matters more.

• A closer.
• Relentless cadence and follow-up.
• Comfortable asking for the business, negotiating with a CFO, and walking a deal through procurement and security review without losing momentum.

• Executive poise.
• Credible in the room with a COO, CIO, or CEO of a multi-site group.
• Enterprise professionalism in how you write, present, and handle pressure.

• You've made other sellers better. Formal management, player-coach, or informal mentoring with results the reps could point to.
• Hands-on with the product. You run your own demos and you're comfortable getting deep on EHR integrations, workflows, and how OhMD AI actually behaves on a call.
• Active use of AI in your own work. Research, account planning, drafting, prep.

Preferred

• Experience selling AI, voice, contact center, or patient engagement technology into healthcare
• Existing relationships with multi-site groups, MSOs, or PE-backed physician platforms
• Founder or early employee at a startup that had to find its first fifty customers
• Working knowledge of the EHR landscape
• Prior player-coach experience at a Series A-C company

Pay and benefits

Pay range $200,000—$300,000 USD