Regional Vice President – Health Plan Sales

Role Overview

• Own and exceed your quota by securing new strategic partnerships with regional and national health plans across Commercial, Medicare Advantage, and Managed Medicaid lines of business, driving multi-million-dollar contracts focused on digital behavioral health integration and value-based outcomes.
• Proactively identify market trends and customer challenges, leveraging cross-functional expertise to develop innovative solutions that address long-term business opportunities and enhance departmental effectiveness.
• Design and lead scalable, end-to-end payer sales processes — including consultative pitching, negotiation, and contracting — optimized for payer procurement standards, long contracting cycles, and consistent execution across partnerships.
• Build and maintain trusted relationships with senior executives across Network, Behavioral Health, Medical Management, Clinical Strategy, and Product teams within payer organizations to deeply understand plan priorities and member population needs.
• Collaborate closely with Market Development, Health Plan Strategy, and Product teams to build regional go-to-market plans and advance pipeline opportunities across payer segments.
• Partner with ecosystem partners and health plan innovation teams to co-develop pilots, expand shared-savings arrangements, and amplify reach within payer networks.
• Serve as a strategic expert in the behavioral health and digital health payer landscape, leveraging insights into VBC trends, parity regulations, and emerging reimbursement models to shape Headspace’s health plan sales approach.
• Provide accurate forecasting and pipeline analytics to inform payer growth strategy, contract cycle timing, and revenue forecasting across Commercial and Government lines.
• Represent Headspace at key payer and digital health industry events (AHIP, HLTH, Medicaid Innovation Forum, Sales Advantage, etc.) to enhance visibility, strengthen plan relationships, and drive thought leadership in behavioral health innovation.
• Collaborate with sales leadership to identify departmental growth opportunities and organizational skill gaps, providing mentorship, facilitating knowledge sharing, and creating challenging development opportunities for team members to enhance overall sales effectiveness.
• Travel as needed (~30%) to advance key deals and attend in-person meetings or events.

Requirements

• 8+ years of experience selling digital health, behavioral health, or population health solutions into payer organizations, with a strong track record of exceeding multi-million-dollar quota targets.
• Proven ability to sell complex solutions into health plan executives — including Network, Behavioral Health, Product, and Clinical Operations leaders — ideally with deal sizes exceeding $1M in annual recurring revenue.
• Deep understanding of the U.S. payer ecosystem, including Commercial, Medicare Advantage, and Medicaid lines, as well as behavioral health parity, value-based care models, and digital health reimbursement mechanisms.
• Strong consultative selling, negotiation, and executive presence with the ability to navigate long and strategic sales cycles.
• Ability to navigate complex payer stakeholder landscapes, managing internal cross-functional relationships across Medical Directors, Provider Networks, Behavioral Health, Quality, and Contracting teams.
• Demonstrated ability to identify process, contracting, and implementation gaps within payer organizations, and to design scalable, compliant sales methodologies that enhance team effectiveness, accelerate adoption, and improve customer outcomes.
• Experience applying design thinking principles to sales challenges, with the ability to challenge assumptions and continuously improve sales approaches.
• Excellent communication skills—both written and verbal—and comfort developing business cases and delivering compelling presentations.
• Highly self-motivated, organized, and goal-oriented with a bias for action in a fast-paced, high-growth environment.

Benefits

• Health insurance
• 401(k) matching
• Flexible work hours
• Paid time off
• Remote work options
• Monthly wellness stipend
• Stock awards
• Lifetime Headspace membership
• Generous parental leave