Enterprise Sales Leader, Healthcare

The role

You will lead and develop a high-performing sales team by hiring, onboarding, and coaching AEs. You will own regional performance and forecast accuracy while participating in complex customer deals.

What you will do

• Hire, onboard, and develop AEs across your region
• Coach reps on deal strategy, pipeline management, and execution
• Create a culture of accountability, learning, and collaboration
• Identify and grow future leaders on your team
• Own regional performance and forecast accuracy
• Inspect pipeline quality and help unblock stalled deals
• Drive consistent execution of sales process
• Partner with RevOps to ensure clean data and clear insights
• Join key customer and prospect conversations
• Support pricing, negotiation, and close strategy

Required qualifications

• 10-15+ years of experience in enterprise customer-facing sales role, identifying and closing large accounts
• 5+ years managing, mentoring, and developing a high-performing enterprise sales team
• Experience running and managing end-to-end complex deals ($1M+)
• Exceptional verbal and written communication abilities
• Ability to analyze market trends, identify opportunities, and make data-driven decisions

Nice to have

• Familiarity with the AI landscape, key players, and emerging trends
• Fluency with AI tooling and workflows
• Experience building GTM strategies, building sales teams and sales motions from scratch, or from early stage growth

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 a platform for customer-facing AI agents. It was co-founded by Bret Taylor and Clay Bavor.