Headspace · 1 day ago
Sales Executive, Enterprise
United States
Full-time
Remote
Senior Level, Lead/Staff
$115K/yr - $140K/yr
8+ years expHeadspace is on a mission to transform mental healthcare to improve the health and happiness of the world. The Sales Executive, Enterprise role focuses on driving growth through enterprise sales, managing full-cycle sales processes, and developing strategic relationships with large employers to promote mental health solutions.
Artificial Intelligence (AI)FitnessHealth CareMental HealthmHealthMobile AppsPsychologyTherapeutics
Responsibilities
Own and exceed your quota by closing new logo deals with employers of 7,500+ employees, selling high-ACV (Six and Seven-Figure) multi-product contracts
Manage full-cycle enterprise sales processes including outbound prospecting, discovery, consultative pitching, product demonstration, proposal development, negotiation, and close
Cultivate trusted relationships with senior leaders across Human Resources, Total Rewards, Benefits, and People teams to deeply understand organizational needs and priorities
Collaborate closely with Account Development Executives (BDRs), Consultant Relations, and Marketing to build pipeline and support coordinated regional go-to-market efforts
Partner with key benefits consultants, brokers, and channel partners to amplify market reach and co-sell effectively
Serve as a strategic expert in the mental health benefits space, leveraging industry trends, buyer insights, and competitive dynamics to shape your sales approach
Lead the development of strategic solutions to technical sales challenges, partnering with Sales Ops and leadership to shape sales methodologies and standards
Provide accurate forecasting and pipeline reporting to support revenue planning and team-wide accountability
Partner with Sales Ops and leadership to refine and implement sales excellence processes that support consistency across enterprise deals
Identify market trends and propose innovative solutions in collaboration with cross-functional teams to support long-term business opportunities
Represent Headspace at high-impact industry events and conferences to enhance brand presence and cultivate new enterprise relationships
Contribute to organizational capability building by sharing best practices, coaching peers, and identifying learning opportunities to strengthen sales team effectiveness
Travel as needed (~30%) to advance key deals and attend in-person meetings or events
Qualification
Required
8+ years of experience in enterprise, digital health, or benefits solution sales with a strong track record of exceeding quotas
Proven ability to sell complex solutions into HR/Benefits departments at large employers, ideally with deal sizes over $500,000 in annual contract value
Deep understanding of the U.S. employer benefits ecosystem, including mental health, employee assistance programs (EAP), and wellbeing trends
Strong consultative selling, negotiation, and executive presence with the ability to navigate long and strategic sales cycles
Ability to manage multiple stakeholders, including HR, Finance, Procurement, and external brokers/consultants
Demonstrated ability to identify process gaps and implement improved sales methodologies that enhance team effectiveness and 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
Comfortable using CRM tools like Salesforce to manage pipeline and forecast accurately
Preferred
Existing relationships within the benefits consulting or brokerage ecosystem
Experience working in a mission-driven or healthcare-focused organization
Familiarity with mental health or behavioral health terminology and delivery models
Benefits
Comprehensive healthcare coverage
Monthly wellness stipend
Retirement savings match
Lifetime Headspace membership
Generous parental leave
Company
Headspace
Headspace is a mental health company offering AI companionship, coaching, therapy, psychiatry, and mindfulness tools for everyday support.
501-1000 employees
Funding
Current Stage
Late StageTotal Funding
$320.85MKey Investors
Oxford Finance LLCBliscePacific Western Bank
2023-07-26Debt Financing· $105M
2022-02-14Series C
2021-10-31Secondary Market
Leadership Team
Tom Pickett
Chief Executive Officer
Andy Puddicombe
Co-Founder
Recent News
2026-01-09
2026-01-08
Company data provided by crunchbase