Enterprise Sales Executive, Headspace Health

• 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
• Candidates must permanently reside in the US full-time

Desirable

• The Sales Executive, Enterprise Sales sits on our Employer Sales team, which is focused on bringing Headspace’s full suite of mental health and wellbeing solutions to large enterprise employers globally
• This team is on the frontlines of advancing our mission to transform the health and happiness of the world, one workplace at a time
• Over the past year, we’ve deepened our market presence through impactful partnerships with organizations committed to employee mental health
• With growing demand for integrated, evidence-based benefits, we’re expanding our enterprise sales force to drive meaningful growth
• This enterprise role operates at a senior level while focusing on market development
• The position requires enterprise-wide influence, cross-functional leadership, and the ability to mentor junior sellers as part of developing sales capabilities across the organization
• This is an exciting opportunity to shape how the largest employers in the world support their people—and to directly contribute to the continued success of Headspace’s B2B business
• 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