Sales Executive, Enterprise

Headspace 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.

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

Requirements:

• 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
• 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