Account Executive

• 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.

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