Head of Sales

About this role

MISSION

Build The Path's B2B revenue engine from zero. You personally take our first deals from initial conversation to signature across employers, providers, and strategic partners, converting warm introductions and outbound hustle alike into signed six- and seven-figure contracts. Because we are early, every deal is also evidence: you work with the founders to figure out which channels convert, at what price, and on what cycle, so the company knows where to double down. As the motion proves out, you document the playbook and hire the team that scales it.

WHO YOU ARE

You were an early or senior sales leader at a digital health or behavioral health company that grew from zero to real revenue. You sold into employers, you know the benefits consultants and brokers, and you have personally closed six- and seven-figure contracts for a product that was new to its buyers. You are comfortable being the entire sales function for a while: sourcing your own pipeline, running your own process, and closing without support. You want to run that arc again from the beginning, with more ownership, in a category that matters.

OUTCOMES

- Close the first contracts: Personally sign our first customers within 12 months, a mix of paid pilots and six- and seven-figure contracts, including at least one flagship account that expands.

- Convert VIP introductions into contracts: Take CEO-level introductions from founders and advisors and personally run them to signature without hand-holding.

- Determine where we win: Within 12 months, establish from real deal evidence which channels convert, at what price, and on what sales cycle.

- Build the repeatable motion: Maintain an honest pipeline with real forecasts, and document the playbook (targeting, pitch, pricing, proposal, close) so the reps you later hire can run it.

COMPETENCIES

- Proven Digital Health Hunter: 10+ years personally sourcing and closing six- and seven-figure deals, selling digital health or benefits products into employers. You generate your own pipeline; you are not a sales ops person or an account manager.

- Deal-Risk Savvy: You know where these deals die (security review, legal, clinical scrutiny, budget cycles) and you address those risks early.

- Comfortable at Altitude: Credible and composed with Fortune 500 CEOs, celebrity founders, and billionaire investors, and you convert those rooms into next steps and contracts.

- Strategic and Operational on the Same Day: You can pressure-test pricing and channel strategy in the morning and send thirty researched outreach emails in the afternoon.

- Autonomous and Disciplined: You operate at high velocity in ambiguity with zero hand-holding, and your pipeline stages, forecasts, and follow-ups are always real.

- Team Builder: You have hired and managed sellers and can build the team once the motion is proven. A path to revenue leadership exists if you earn it, but you are hired to sell.

- Genuine Conviction: You care about mental health and it shows. Buyers can sense whether it is real.

GREAT TO HAVE

- Sold into, against, or through EAPs; relationships with benefits consultants and brokers.

- Breadth beyond employers: providers, health systems, payers, or distribution partnerships.

- Sold clinical or evidence-based products where outcomes data is part of the sale.

- First sales hire at an early-stage startup.

- Personal connection to therapy, coaching, or mental health.

LOGISTICS

- San Francisco, hybrid (Tue-Thu in office). Not remote. Full-time.

- Reports to the CEO.

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