Enterprise Sales Director - Strategic, Healthcare

Highlights

• Lead Sierra's largest multi-BU, multi-geo deals for healthcare customers.
• Healthcare agents already reach over 50% of U.S. families.
• Build AI agents that make care more accessible, human and affordable.

What they offer

• Flexible (unlimited) paid time off
• Medical, dental, and vision benefits
• Life insurance and disability benefits
• Parental leave
• Fertility and family building benefits through Carrot
• Lunch, snacks and coffee
• Discretionary benefit stipend
• Equity plans

Ideal candidate

A strategic enterprise seller who thrives on complex, C-suite-led deals and operates with precision and trust. You care deeply about transforming healthcare and making care more human and accessible.

Requirements

• 10-12+ years of enterprise/strategic sales experience, owning the largest and most complex accounts
• Demonstrated success closing multi-million-dollar, multi-stakeholder deals spanning business units and geographies
• Experience managing a $1M+ quota and running end-to-end complex 6- and 7-figure ACV deals
• Deep, sustained C-suite relationships and the gravitas to be treated as a peer by executive buyers
• Mastery of complex deal structuring, risk navigation, and pricing
• Exceptional executive communication and a reputation for precision and trust