Enterprise Sales Director - Strategic, Healthcare

Highlights

• Lead Sierra's largest multi-BU, multi-geo healthcare deals.
• Healthcare agents already reach over 50% of U.S. families.
• Partner with health plans and providers to make care more human.

What they offer

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

Ideal candidate

A seasoned strategic seller with C-suite gravitas and precision who thrives on complex, high-stakes healthcare deals and cares deeply about making care more accessible and human.

Requirements

• 10-12+ years of enterprise/strategic sales experience owning largest, most complex accounts
• Demonstrated success closing multi-million-dollar, multi-stakeholder deals across BUs and geographies
• Experience managing $1M+ quota and running end-to-end 6- and 7-figure ACV deals
• Deep, sustained C-suite relationships with executive presence as a trusted peer
• Mastery of complex deal structuring, risk navigation, pricing and executive communication