Regional Vice President, Health Plan Sales

About the Regional Vice President, Health Plan Sales at Headspace:

Headspace is on a mission to transform mental healthcare to improve the health and happiness of the world. Through our integrated mental health and wellbeing platform, we provide evidence-based care and engaging experiences to individuals and organizations everywhere. Our products make it easier for people to access care, build resilience, and thrive — at home, at work, and beyond.

The Regional Vice President (RVP), Health Plan Sales sits on our Health Plan Sales team, which focuses on bringing Headspace’s full suite of mental health and wellbeing solutions to Commercial and Managed Medicare and Medicaid health plans nationally. This team leads our efforts to expand access to evidence-based behavioral health across payer populations, helping plans drive member engagement, improve outcomes, and achieve value-based care goals.

With growing demand for integrated, outcomes-driven behavioral health solutions, we’re expanding our health plan sales organization to deepen relationships with health plans and deliver measurable impact across populations. This role operates at a senior level while focusing on market development. The position requires company-wide influence, cross-functional leadership, and the ability to mentor junior sellers as part of developing sales capabilities across the organization. This is an exciting opportunity to shape how leading health plans design and deliver behavioral health solutions that improve access, affordability, and outcomes for their members.

What you will do:

• 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.

What you will bring:

Required Skills:

• 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.

Preferred Skills:

• Existing executive relationships within regional and national health plans, PBMs, or health system partners.
• Experience working in a mission-driven or healthcare-focused organization.
• Familiarity with mental health or behavioral health terminology and delivery models.

Location:

We are currently hiring this role remotely in the US and Hybrid for San Francisco (SF). Candidates must permanently reside in the US full-time.
For candidates with a primary residence in the greater SF area, this role will follow our hybrid model. You’ll work 3 days per week from our office, allowing for impactful in-office collaboration and connection, while enjoying the flexibility of remote work for the rest of the week. Your recruiter will share more details about our hybrid model.

Pay & Benefits:

The anticipated new hire base salary range for this full-time position is $136,800-$165,000 base + quarterly variable + equity + benefits.

Our salary ranges are based on the job, level, and location, and reflect the lowest to highest geographic markets where we are hiring for this role within the United States. Within this range, individual compensation is determined by a candidate’s location as well as a range of factors including but not limited to: unique relevant experience, job-related skills, and education or training.
Your recruiter will provide more details on the specific salary range for your location during the hiring process.

At Headspace, base salary is but one component of our Total Rewards package. We’re proud of our robust package inclusive of: base salary, stock awards, comprehensive healthcare coverage, monthly wellness stipend, retirement savings match, lifetime Headspace membership, generous parental leave, and more. Additional details about our Total Rewards package will be provided during the recruitment process.

About Headspace

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.

Why You’ll Love Working Here:

• 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

How we feel about Diversity, Equity, Inclusion and Belonging:

Headspace is committed to bringing together humans from different backgrounds and perspectives, providing employees with a safe and welcoming work environment free of discrimination and harassment. We strive to create a diverse & inclusive environment where everyone can thrive, feel a sense of belonging, and do impactful work together.

As an equal opportunity employer, we prohibit any unlawful discrimination against a job applicant on the basis of their race, color, religion, gender, gender identity, gender expression, sexual orientation, national origin, family or parental status, disability*, age, veteran status, or any other status protected by the laws or regulations in the locations where we operate. We respect the laws enforced by the EEOC and are dedicated to going above and beyond in fostering diversity across our workplace.

*Applicants with disabilities may be entitled to reasonable accommodation under the terms of the Americans with Disabilities Act and certain state or local laws. A reasonable accommodation is a change in the way things are normally done which will ensure an equal employment opportunity without imposing undue hardship on Headspace. Please inform our Talent team by filling out this form if you need any assistance completing any forms or to otherwise participate in the application or interview process.

---

Headspace participates in the E-Verify Program.

Privacy Statement

All member records are protected according to ourPrivacy Policy. Further, while employees of Headspace (formerly Ginger) cannot access Headspace products/services, they will be offered benefits according to the company's benefit plan. To ensure we are adhering to best practice and ethical guidelines in the field of mental health, we take care to avoid dual relationships. A dual relationship occurs when a mental health care provider has a second, significantly different relationship with their client in addition to the traditional client-therapist relationship—including, for example, a managerial relationship.

As such, Headspace requests that individuals who have received coaching or clinical services at Headspace wait until their care with Headspace is complete before applying for a position. If someone with a Headspace account is hired for a position, please note their account will be deactivated and they will not be able to use Headspace services for the duration of their employment.

Further, if Headspace cannot find a role that fails to resolve an ethical issue associated with a dual relationship, Headspace may need to take steps to ensure ethical obligations are being adhered to, including a delayed start date or a potential leave of absence. Such steps would be taken to protect both the former member, as well as any relevant individuals from their care team, from impairment, risk of exploitation, or harm.

For how how we will use the personal information you provide as part of the application process, please see: https://www.headspace.com/applicant-notice