Enterprise Sales Director – Strategic Healthcare

About the role

The Enterprise Sales Director – Strategic Healthcare leads Sierra’s most complex, multi‑business‑unit and multi‑geography deals in the healthcare space. You will partner directly with C‑suite executives, co‑founders, and internal teams to design sophisticated deal structures and drive high‑value outcomes for both customers and Sierra.

Key responsibilities

• Architect Sierra's largest, most complex deals, shaping sophisticated structures and managing risk with precision.
• Build and maintain trusted relationships across the customer C‑suite and working teams, acting as an extension of the client’s organization.
• Engage regularly with Sierra’s co‑founders in front of customers, delivering pitches with founder‑level conviction.
• Maintain exacting craft in messaging, positioning, and timing for every interaction.
• Influence Sierra’s account strategy, setting standards for the broader sales organization.
• Leverage AI tools throughout the sales cycle—from research and outreach to pipeline forecasting and deal execution—to automate low‑value tasks and focus on high‑value relationships.

Required profile

• 10‑12+ years of enterprise/strategic sales experience handling the largest and most complex accounts.
• Proven success closing multi‑million‑dollar, multi‑stakeholder deals across business units and geographies.
• Experience managing a $1M+ quota and leading end‑to‑end 6‑ and 7‑figure ACV transactions.
• Deep, sustained C‑suite relationships with the gravitas to be treated as a peer by executive buyers.
• Mastery of complex deal structuring, risk navigation, and pricing.
• Exceptional executive communication and a reputation for precision and trust.
• Deep familiarity with the AI landscape and ability to speak credibly to technical and business stakeholders.
• Experience operating alongside founders or executives in front of strategic customers.

What we offer

• Flexible (unlimited) paid time off.
• Medical, dental, and vision benefits for you and your family.
• Life insurance and disability benefits.
• Retirement plan dependent on country of employment.
• Parental leave.
• Fertility and family‑building benefits through Carrot.
• Lunch, snacks, and coffee to keep you energized.
• Discretionary benefit stipend for personal priorities.
• Free alphorn lessons.