Regional Vice President, Health Plan Sales

8+ years of experience selling digital health, behavioral health, or population health solutions into payer organizations. Proven ability to sell complex solutions into health plan executives. Deep understanding of the U.S. payer ecosystem, including Commercial, Medicare Advantage, and Medicaid lines. Strong consultative selling, negotiation, and executive presence. Ability to navigate complex payer stakeholder landscapes. Demonstrated ability to identify process, contracting, and implementation gaps within payer organizations. Experience applying design thinking principles to sales challenges. Excellent communication skills—both written and verbal. Highly self-motivated, organized, and goal-oriented.

Own and exceed quota by securing new strategic partnerships with regional and national health plans. Proactively identify market trends and customer challenges to develop innovative solutions. Design and lead scalable, end-to-end payer sales processes. Build and maintain trusted relationships with senior executives across health plan organizations. Collaborate with teams to build regional go-to-market plans and advance pipeline opportunities. Partner with ecosystem partners to co-develop pilots and expand shared-savings arrangements. Serve as a strategic expert in the behavioral health and digital health payer landscape. Provide accurate forecasting and pipeline analytics. Represent Headspace at key payer and digital health industry events. Collaborate with sales leadership to identify departmental growth opportunities and provide mentorship.