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:

• 8+ years of experience growing and expanding digital health, behavioral health, or population health partnerships within payer organizations, with a proven record of exceeding multi-million-dollar quota targets through renewals, upsells, and new business acquisition.
• Proven ability to expand and cross-sell complex digital health solutions to senior health plan executives — including Network, Behavioral Health, Product, and Clinical Operations leaders — with demonstrated success driving renewals and new multi-million-dollar contracts.
• Deep understanding of the U.S. payer ecosystem — including Commercial, Medicare Advantage, and Medicaid — with expertise in behavioral health parity, value-based care models, and reimbursement mechanisms that inform expansion and integration strategies across existing plan partnerships.
• Strong consultative selling, negotiation, and executive presence with the ability to manage renewal and expansion discussions, navigate long contracting cycles, and maintain trusted relationships across payer stakeholders.
• Ability to navigate complex payer stakeholder landscapes, managing cross-functional relationships and collaborating with internal teams to identify expansion opportunities, strengthen existing partnerships, and drive cross-functional alignment.
• Demonstrated ability to identify renewal and contracting barriers within payer organizations, and to design scalable, compliant sales methodologies that accelerate expansion, improve adoption, and strengthen payer relationships.
• Experience applying design thinking principles to refine and expand payer relationships, continuously improving sales approaches to maximize renewal rates, customer satisfaction, and expansion outcomes.
• Excellent communication and storytelling skills, with the ability to frame compelling expansion business cases and deliver persuasive presentations to payer executives and internal cross-functional teams.
• Highly motivated and goal-driven, with a growth mindset focused on nurturing long-term payer partnerships, driving expansion, and thriving in a fast-paced, high-growth environment.
• Proficient in CRM tools like Salesforce to manage expansion and renewal pipelines, forecast growth opportunities, and maintain visibility across payer relationship stages.

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) 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. 

Pay & Benefits:

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.

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.

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Headspace participates in the E-Verify Program.

Privacy Statement

All member records are protected according to our Privacy 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