Sales Executive, Enterprise

About the Sales Executive, Enterprise at Headspace 

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.

What you will do:

• 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.
• Identify and propose strategic approaches to technical sales challenges affecting the enterprise team, establish sales standards, and drive adoption of solution-based selling methodologies
• 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 identifying skill gaps, providing mentorship, and creating development opportunities for other team members to enhance overall sales effectiveness.
• Support capability-building across the team by sharing best practices, mentoring peers, and contributing to learning opportunities.
• 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 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 Sk