Regional Vice President, Enterprise Sales

Summary

Join Headspace as a Regional Vice President (RVP), Enterprise Sales and contribute to their mission of transforming the health and happiness of the world. This role focuses on selling Headspace's mental health and wellbeing solutions to large enterprise employers globally. You will be responsible for exceeding your quota by closing new deals with employers of 7,500+ employees, managing full-cycle enterprise sales processes, cultivating trusted relationships with senior leaders, collaborating with other teams, and serving as a strategic expert in the mental health benefits space. You will also identify and propose solutions to technical sales challenges, provide accurate forecasting and pipeline reporting, design and implement sales excellence processes, proactively identify market trends and customer challenges, represent Headspace at industry events, and contribute to organizational capability building. This role requires 8+ years of experience in enterprise, digital health, or benefits solution sales with a proven track record of exceeding quotas.

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

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
• 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
• Design and implement sales excellence processes that enhance quality and consistency across enterprise deals, ensuring high-impact outcomes for both customers and Headspace
• Proactively identify market trends and customer challenges, leveraging cross-functional expertise to develop innovative solutions that address long-term business opportunities and enhance departmental effectiveness
• 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
• Collaborate with sales leadership to identify departmental growth opportunities and build capabilities through knowledge sharing, skill development, and creating challenging assignments for team members
• Travel as needed (~30%) to advance key deals and attend in-person meetings or events in the East Coast region

Preferred Qualifications

• 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

Benefits

• The anticipated new hire base salary range for this full-time position is $115,000-$150,000 + quarterly variable + equity + benefits
• The annual on-target earnings for this role is $230,000-$300,000 (at 100% quota attainment)
• Our salary ranges are based on the job, level, and location, and reflect the lowest to highest geographic markets where we are hiring for this role within the United States
• Within this range, individual compensation is determined by a candidate’s location as well as a range of factors including but not limited to: unique relevant experience, job-related skills, and education or training
• Your recruiter will provide more details on the specific salary range for your location during the hiring process
• At Headspace, base salary is but one component of our Total Rewards package
• We’re proud of our robust package inclusive of: base salary, stock awards, comprehensive healthcare coverage, monthly wellness stipend, retirement savings match, lifetime Headspace membership, generous parental leave, and more
• Additional details about our Total Rewards package will be provided during the recruitment process