Head of Sales

The Path • San Francisco Bay Area, CA

7d • Hybrid

About The Position

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.

Requirements

• 10+ years personally sourcing and closing six- and seven-figure deals, selling digital health or benefits products into employers.
• Generate your own pipeline; you are not a sales ops person or an account manager.
• Know where these deals die (security review, legal, clinical scrutiny, budget cycles) and address those risks early.
• Credible and composed with Fortune 500 CEOs, celebrity founders, and billionaire investors, and you convert those rooms into next steps and contracts.
• Can pressure-test pricing and channel strategy in the morning and send thirty researched outreach emails in the afternoon.
• Operate at high velocity in ambiguity with zero hand-holding, and your pipeline stages, forecasts, and follow-ups are always real.
• Have hired and managed sellers and can build the team once the motion is proven.
• Care about mental health and it shows. Buyers can sense whether it is real.

Nice To Haves

• 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.

Responsibilities

• 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.
• Take CEO-level introductions from founders and advisors and personally run them to signature without hand-holding.
• Establish from real deal evidence which channels convert, at what price, and on what sales cycle within 12 months.
• 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.

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed