Senior Director, Health Plan Sales

About the Senior Director, Health Plan Sales at Headspace :

The Senior Director, 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 individual contributor level, with a focus on strategic deal execution, cross‑functional collaboration, and contribution to scalable growth within the payer vertical. 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 expanding and deepening partnerships within existing regional and national health plans across Commercial, Medicare Advantage, and Medicaid lines of business, while pursuing new strategic opportunities that drive multi‑million‑dollar contracts focused on digital behavioral health integration and value‑based outcomes.
• Proactively identify growth opportunities within existing payer partnerships by leveraging cross‑functional expertise to co‑develop innovative solutions that address customer needs, strengthen plan relationships, and drive long‑term business impact.
• Execute and continuously improve scalable payer sales processes — including consultative pitching, negotiation, and contracting — in alignment with payer procurement standards and supported by sales leadership.
• Strengthen and expand trusted relationships with senior executives across Network, Behavioral Health, Medical Management, and Clinical Strategy teams within payer organizations to drive deeper integration, renewals, and expansion opportunities aligned with member and plan priorities.
• Partner with Market Development, Health Plan Strategy, and Product teams to support development of go‑to‑market strategies and contribute to expansion planning by surfacing customer needs and market insights.
• 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 data‑driven forecasting and pipeline analytics to inform expansion strategy within existing payer accounts, optimize contract renewal timing, and identify new revenue opportunities across Commercial and Government lines.
• Represent Headspace at select payer and digital health industry events (e.g., AHIP, HLTH, Medicaid Innovation Forum), in coordination with sales leadership, to support visibility and foster external relationships that advance priority deals.
• Provide insights and best practices with sales peers and cross‑functional teams to support collective learning. Collaborate with sales leadership by providing input on market trends and expansion opportunities to refine team‑wide sales strategies.
• Travel as needed (~30%) to advance key deals and attend in‑person meetings or events.

What you will bring

Required Skills

Preferred Skills

Location

We are currently hiring this role remotely in the US and Hybrid for San Francisco (SF) and Los Angeles (LA). Candidates must permanently reside in the US full‑time. For candidates with a primary residence in the greater SF and LA areas, 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.

Compensation

The anticipated new hire base salary range for this full‑time position is $101,300 - $138,000 + 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.

Benefits

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

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

Accommodations

Applicants who need assistance completing the application or interview process, or who are ineligible to complete certain sections of the application or interview process due to a disability, can contact our Talent team by completing this form to receive reasonable accommodations.

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

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