Enterprise Sales Director - Majors, Healthcare

About the role

Sierra is a leading platform for customer-facing AI agents that partners with major brands to transform customer service and business growth. As an Enterprise Sales Director, you will independently drive complex enterprise deals, manage high-value accounts, and build relationships with C-suite stakeholders. You will leverage AI tools to optimize the sales cycle and contribute to the company's mission of making healthcare more accessible and human.

Responsibilities

• Manage a broad enterprise book with strong autonomy, leading 6- and 7-figure deal cycles from prospecting to close.
• Lead VP-level conversations and build durable C-suite relationships across customer organizations.
• Identify and manage deal risk early and build rigorous stakeholder maps for accounts.
• Partner with management on pricing, escalation timing, executive alignment, and deal strategy.
• Bring in co-founders effectively for executive engagement when it moves a deal.
• Act as a visible, steady leader on deal teams and proactively elevate the team's standard.
• Leverage AI tools across the full sales cycle to automate low-value tasks and focus on high-value customer relationships.

Required skills

• Enterprise sales
• Account management
• C-suite relationship building
• Deal strategy
• Pipeline forecasting
• Analytical mindset

Nice to have

• AI landscape knowledge

Benefits

• Flexible unlimited paid time off
• Medical, dental, and vision benefits
• Life insurance
• Disability benefits
• Retirement plan
• Parental leave
• Fertility and family building benefits
• Lunch and snacks
• Discretionary benefit stipend
• Alphorn lessons

About the Company

Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands to transform how they serve customers and grow their businesses. The company is guided by values including Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing family.