Enterprise Sales Director – Strategic, Healthcare

This is a fully remote position, open to applicants in United States.

📋 Description

• Oversee the most extensive and intricate opportunities involving multiple business units and geographic locations.

• Create advanced deal frameworks and manage associated risks.

• Establish and nurture trusted relationships within customer C-suites and operational teams.

• Collaborate with and engage Sierra’s co-founders during customer interactions.

• Propel accurate messaging, positioning, and timing throughout all engagements.

• Shape Sierra’s strategy for key accounts and set benchmarks for the wider sales team.

• Utilize AI tools for account research, tailored outreach, call summarization, pipeline forecasting, and deal execution.

• Streamline low-value sales activities to dedicate more time to high-value customer interactions.

• Regularly explore and implement new AI solutions.

⛳️ Requirements

• 10–12+ years of experience in enterprise/strategic sales, managing the largest and most intricate accounts.

• Proven track record of successfully closing multi-million-dollar deals involving multiple stakeholders across various business units and regions.

• Experience managing a quota of $1M or more.

• Proficiency in handling complex 6- and 7-figure ACV deals from start to finish.

• Established, long-term relationships at the C-suite level.

• Presence and gravitas to be regarded as a peer by executive buyers.

• Expertise in complex deal structuring, risk management, and pricing strategies.

• Outstanding executive-level communication skills.

• A strong reputation for accuracy and reliability.

• In-depth knowledge of the AI landscape.

• Capability to engage credibly with both technical and business stakeholders.

• Experience collaborating with founders and executives in front of strategic clients.

• Legally eligible to work in the United States.

• Must indicate whether United States visa sponsorship is necessary.

🏝️ Benefits

• Flexible (unlimited) paid time off.

• Medical, dental, and vision benefits for you and your family.

• Life insurance and disability coverage.

• Retirement plan based on the country of employment.

• Parental leave.

• Fertility and family-building benefits through Carrot.

• Lunch, tasty snacks, and coffee provided.

• Discretionary benefit stipend.

• Complimentary alphorn lessons.

• Equity plans available for eligible full-time employees.

• Commission opportunities.

• Equity.