Enterprise Sales Director - Majors, Healthcare

The role

You will drive complex enterprise deals end-to-end by managing a broad book of business. You will lead 6- and 7-figure deal cycles and build relationships with C-suite stakeholders.

What you will do

• Independently drive complex enterprise deals end-to-end
• Manage a broad enterprise book with strong autonomy
• Lead 6- and 7-figure deal cycles from prospecting to close
• Multi-thread to the C-suite and build durable relationships
• Identify and manage deal risk early
• Build rigorous stakeholder maps for accounts
• Partner with manager on pricing, escalation, and deal strategy
• Leverage co-founders for exec engagement
• Act as a visible, steady leader on deal teams
• Operate as an AI-native seller using AI tools across the sales cycle

Required qualifications

• 8- 10 years of enterprise customer-facing sales experience
• Experience managing a $1M+ quota
• Experience running end-to-end 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
• Analytical mindset

Nice to have

• Familiarity with the AI landscape, key players, and emerging trends

Benefits

• 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
• Lunch, as well as delicious snacks and coffee when working onsite
• Discretionary benefit stipend
• Free alphorn lessons
• Equity plans for eligible full-time employees

About the company

Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands. The company is primarily an in-person company based in San Francisco.