Regional Vice President, Health Plan Sales

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.

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A mission that matters—with impact you can see and feel

A culture that’s collaborative, inclusive, and grounded in our values

The chance to shape what mental health care looks like next

Competitive pay and benefits that support your whole self

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.

Headspace exists to provide every person access to lifelong mental health support. We combine evidence-based content, clinical care, and innovative technology to help millions of members around the world get support that’s effective, personalized, and truly accessible whenever and wherever they need it.

At Headspace, our values aren’t just what we believe, they’re how we work, grow, and make an impact together. We live them daily:

Make the Mission Matter, Iterate to Great, Own the Outcome, and Connect with Courage.

These values shape our decisions, guide our collaborations, and define our culture. They’re our shared commitment to building a more connected, human-centered team—one that’s redefining how mental health care supports people today and for generations to come.