• 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.