Director of Health Systems Sales

Building Healthcare That Remembers

Every time you call a doctor's office, the system forgets you the moment you hang up. You wait on hold, explain everything from scratch, get bounced between lines, and hope someone follows up. Everyone has felt this. No one should have to.

At Assort Health, we're building one continuous conversation for every patient. An AI agent that knows who you are, remembers how you like to be reached, and carries that context from your first symptom to your full recovery. What began as the first voice AI agent to schedule a specialty appointment has become the largest proprietary specialty dataset in healthcare: 210 million patient interactions, 62,000 care protocols, 1.6 million decision pathways.

We went from 15 people in 2025 and will cross 250 by the end of 2026. Revenue is up 20x in 15 months and we've raised $222 million, including a recent $120 million Series C at a $1.2 billion valuation. We've also been named to the Forbes Cloud 100 and the 2026 Enterprise Tech 30 as the only healthcare AI company on the list!

Healthcare spends $1.1 trillion a year on administration instead of care.

We're looking for a Director of Health Systems Sales to lead and grow our go-to-market efforts across health systems, clinics, and digital health partners. As an early member of the GTM leadership team, you'll play a critical role in shaping our sales motion, refining playbooks, and driving new business as we scale to the next stage of growth.

You’ll manage a team of Account Executives. The ideal candidate combines sales leadership experience and a deep passion for AI-driven innovation in patient engagement.

We value clarity, accountability, and execution. If you're energized by impact and thrive in fast-paced, mission-driven teams, join us.

• Own pipeline growth and revenue targets across assigned territories or verticals.

• Lead and mentor the sales team
  , providing coaching on discovery, objection handling, and closing strategies.

• Develop and optimize sales playbooks
  , processes, and enablement tools for scalable growth.

• Partner cross-functionally with Marketing, Customer Success, and Product to ensure strong alignment across the GTM funnel.

• Represent Assort Health externally at conferences, webinars, and customer meetings.

• Collaborate with the executive team on pricing, positioning, and market expansion strategy.

• Track and report key metrics
  , including conversion rates, pipeline velocity, and ARR attainment.

• Handle ambiguity and turn order into chaos for the benefit of your team.

• Willingness and ability to travel up to 25% of the time

• 6+ years of experience in B2B SaaS sales
  , with at least 3+ years in a sales leadership or management role
  .

• Experience scaling sales teams at Series A-C stage startups
  .

• Proven success in healthcare technology or a closely related field (EHRs, patient engagement, or digital health).

• Track record of meeting or exceeding team revenue targets in fast-paced environments.

• Selling into health systems

• Excellent communication, leadership, and relationship-building skills.

• Data-driven approach to sales strategy and forecasting.

• Comfortability with CRM tools and sales analytics platforms.

• Strong understanding of the healthcare buyer journey
  .

• Familiarity with AI-driven SaaS or conversational AI products.

• Strong network within healthcare provider, payer, or health tech ecosystems.

• Competitive Compensation - Including salary and employee stock options so you share in our success.

• Lifelong Learning - Annual budget for professional development, plus training opportunities to help you grow.

• Office Setup Stipend - We'll outfit your in-office workspace so comfy as it's productive.

• Top-Tier Health…