Enterprise Sales Director - Majors, Healthcare

About the role

Sierra is seeking an Enterprise Sales Director to manage complex, high-stakes deals within the healthcare sector. You will drive end-to-end sales cycles, build relationships with C-suite stakeholders, and leverage AI-native tools to optimize your sales process. This role is critical to expanding the reach of Sierra's AI agents, which currently serve over 50% of U.S. families.

Responsibilities

• Independently drive complex enterprise deals end-to-end from prospecting to close.
• Lead VP-level conversations and build durable C-suite relationships across customer organizations.
• Identify and manage deal risk early while building rigorous stakeholder maps.
• Partner with management on pricing, escalation, and deal strategy.
• Leverage leadership and co-founders for executive engagement when necessary.
• Act as a visible, steady leader on deal teams to elevate performance standards.
• Operate as an AI-native seller by utilizing AI tools for research, outreach, and forecasting.

Required skills

• Enterprise sales
• C-suite relationship management
• Complex deal management
• Analytical mindset
• Communication

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
• Discretionary benefit stipend
• Lunch, snacks, and coffee

About the Company

Sierra is a leading platform for customer-facing AI agents that partners with major global brands to transform customer service and business growth. Founded by industry veterans, the company is guided by values including trust, customer obsession, craftsmanship, intensity, and a commitment to family.