Sales Executive, Enterprise

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.

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The anticipated new hire base salary range for this full-time position is

$115,000-$140,000

+ quarterly variable + equity + benefits. The annual on-target earnings for this role is

$230,000-$280,000

(at 100% quota attainment)

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.

Headspace exists to provide every person access to lifelong mental health support. We combine evidence-based content, clinical care, and innovative technology to help millions of members around the world get support that’s effective, personalized, and truly accessible whenever and wherever they need it.

At Headspace, our values aren’t just what we believe, they’re how we work, grow, and make an impact together. We live them daily:

Make the Mission Matter, Iterate to Great, Own the Outcome, and Connect with Courage.

These values shape our decisions, guide our collaborations, and define our culture. They’re our shared commitment to building a more connected, human-centered team—one that’s redefining how mental health care supports people today and for generations to come.