Regional Vice President, Health Plan Sales at Headspace

San Francisco, California, United States

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Not SpecifiedCompensation

Senior (5 to 8 years), Expert & Leadership (9+ years)Experience Level

Full TimeJob Type

UnknownVisa

Healthcare, Mental Health, Health InsuranceIndustries

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

Responsibilities

Own and exceed 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

Skills

Key technologies and capabilities for this role

Health Plan SalesPayer SalesSales Quota ManagementStrategic PartnershipsConsultative SellingNegotiationContractingMarket Trend AnalysisCross-Functional LeadershipMentoringValue-Based CareMedicare AdvantageManaged Medicaid

Questions & Answers

Common questions about this position

What is the salary or compensation for the Regional Vice President, Health Plan Sales role?

This information is not specified in the job description.

Is this Regional Vice President role remote or does it require office presence?

This information is not specified in the job description.

What key skills are required for the Regional Vice President, Health Plan Sales position?

The role requires expertise in health plan sales, cross-functional leadership, consultative pitching and negotiation, building executive relationships, and strategic knowledge of behavioral health payer landscape including VBC trends and reimbursement models.

What is the team structure or company culture like for this role at Headspace?

The role sits on the Health Plan Sales team focused on expanding access to mental health solutions for health plans, involves company-wide influence, cross-functional leadership, and mentoring junior sellers to develop sales capabilities.

What makes a strong candidate for the Regional Vice President, Health Plan Sales role?

Strong candidates will have senior-level experience in market development, ability to secure multi-million-dollar contracts with health plans, lead scalable sales processes, and provide strategic expertise in behavioral health payer trends while collaborating cross-functionally.

Headspace

Digital health platform for mindfulness and meditation

About Headspace

Headspace is a digital health platform focused on mindfulness and meditation, aimed at helping individuals improve their mental and physical well-being. The platform offers guided meditation sessions, daily mini-meditations, and exercises tailored for various needs such as sleep, stress, and anxiety. Users can access a limited selection of content for free, but a subscription to Headspace Plus unlocks the full range of services. This subscription model not only provides a steady revenue stream but also allows users to access comprehensive tools for mental health improvement. Headspace distinguishes itself from competitors by offering free access to its premium service for unemployed individuals, showcasing its commitment to supporting mental health during difficult times. The company's goal is to enhance the overall well-being of its users through accessible mindfulness practices.

Santa Monica, CaliforniaHeadquarters

2010Year Founded

$170.6MTotal Funding

DEBTCompany Stage

Consumer Software, HealthcareIndustries

1,001-5,000Employees

Benefits

Unlimited Vacation

Catered Lunch

Fully Paid Health Care

Competitive Salaries

Free gym membership

Risks

Increased competition from fitness apps with mental health features.

Recent layoffs may indicate financial instability or restructuring challenges.

Partnership with TikTok could expose Headspace to reputational risks.

Differentiation

Headspace offers a unique AI companion, Ebb, for personalized mental health support.

The platform provides free premium access to unemployed users, showcasing social responsibility.

Headspace's partnership with Uwill expands its reach into the higher education sector.

Upsides

Growing demand for digital mental health solutions boosts Headspace's user base.

Partnership with TikTok enhances visibility among younger demographics.

Fertility journey collection taps into a niche market, attracting new users.

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