Head of Enterprise Sales (AI Healthcare)

TL;DR

Head of Enterprise Sales (AI Healthcare): Building and scaling enterprise revenue for an AI-native healthcare platform with an accent on strategic account acquisition, complex health-system sales, and enterprise sales team development. Focus on closing seven-figure deals, navigating multi-stakeholder procurement and executive relationships, and creating a predictable go-to-market engine.

Location: San Francisco Bay Area or remote within the United States

Salary: $250,000 base plus $250,000 commission; $500,000 OTE

Company

Healthcare technology company building an AI operating system for care delivery, clinical documentation, patient workflows, and revenue cycle management.

What you will do

• Own the enterprise revenue quota, strategic deals, new-logo acquisition, and expansion revenue across health systems and large healthcare organizations.
• Hire, develop, and coach enterprise account executives while establishing standards for pipeline management, discovery, executive engagement, and deal execution.
• Define the enterprise go-to-market motion, including ICP targeting, outbound strategy, sales-cycle architecture, competitive positioning, and deal structure.
• Build C-suite relationships with clinical and administrative leaders, including CMOs, CFOs, CIOs, CNOs, and COOs.
• Partner with Marketing, RevOps, Product, Clinical, and Implementation teams to improve pipeline predictability, product-market alignment, and post-sale execution.
• Lead complex multi-product opportunities through proposal development, procurement, legal and security reviews, forecasting, and close.

Requirements

• 10+ years of enterprise sales experience, including 3–5 years leading an enterprise sales function.
• Proven success closing seven-figure enterprise healthcare deals and navigating complex health-system procurement cycles.
• Experience building and scaling an enterprise sales team through hiring, ramping, coaching, and quota attainment.
• Established relationships with C-suite clinical and administrative leadership at health systems.
• Background in a high-growth health tech, digital health, or enterprise SaaS company.

Nice to have

• Experience with AI, ambient documentation, revenue cycle management, or clinical workflow technology.
• Experience at a company that scaled through a significant fundraise, acquisition, or IPO preparation.
• Existing C-suite relationships at major US health systems.
• Experience running direct and channel or partnership-driven enterprise sales motions in parallel.
• Experience collaborating with clinical implementation and customer success teams on complex post-sale delivery.

Culture & Benefits

• Work directly alongside clinicians and see the impact of shipped products on patient care.
• Fast-paced environment with daily deployments and end-to-end ownership.
• Opportunity to influence healthcare transformation and reduce administrative burden.
• Employees must follow information security policies and report confirmed or potential security events.