Enterprise Sales Director – Healthcare Majors

About the role

The Enterprise Sales Director will own complex, high‑value enterprise deals in the healthcare sector, driving end‑to‑end sales cycles from prospecting to close. You will work closely with C‑suite executives, manage risk, and leverage AI tools to accelerate the sales process.

Key responsibilities

• Independently drive complex enterprise deals end‑to‑end, managing 6‑ and 7‑figure cycles.
• Multi‑thread to the C‑suite, building durable relationships with VP‑level and executive stakeholders.
• Identify and manage deal risk early, creating rigorous stakeholder maps.
• Partner with managers on pricing, escalation, executive alignment, and deal strategy.
• Engage Sierra’s co‑founders for executive involvement when it moves a deal forward.
• Raise the bar as a visible leader on deal teams, proactively elevating standards.
• Operate as an AI‑native seller, using AI tools for research, outreach, summarization, forecasting, and execution.

Required profile

• 8–10 years of enterprise customer‑facing sales experience, closing large accounts.
• Experience managing a $1M+ quota and handling complex 6‑ and 7‑figure ACV deals.
• Proven ability to multi‑thread and build trusted relationships across customer C‑suites.
• Exceptional verbal and written communication skills.
• Analytical mindset with data‑driven decision making.
• Familiarity with the AI landscape, key players, and emerging trends (preferred).

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.
• Free alphorn lessons.