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Head of Employer Sales (Hybrid)

Boston, MA

At Wellist, we’ve spent the last 10 years helping people navigate life’s most challenging moments. After a decade of proven impact serving health systems, we have pivoted into the employer space —and we’re now scaling rapidly. Our platform empowers employers to deliver the right resources at the right time, so employees feel supported through every life moment and HR leaders can maximize the value of their benefit investments. 

It’s an exciting inflection point: you’ll be joining a company with the stability of a seasoned organization and the momentum of a high-growth expansion. As our Head of Employer Sales, you'll lead Wellist's rapid commercial expansion into the large, enterprise employer market through a combination of relationship building, dealmaking and market positioning.

What You’ll Do

  • Own full-cycle enterprise sales to CHROs and Total Rewards leaders at mid-to-large employers—from prospecting through close.
  • Manage and build on an existing pipeline while developing targeted prospecting strategies to open new employer relationships.
  • Close multi-million-dollar ACV deals with typical sales cycles of 6–9 months.
  • Partner directly with the CEO and Senior Commercial Advisors on high-stakes enterprise opportunities while independently driving key deals.
  • Refine and scale our employer sales playbook by identifying what works, improving it, and making it repeatable.
  • Bring timely market intelligence to Product and Marketing to strengthen our employer positioning and inform our GTM evolution.

What Success Looks Like

3 months in: Pipeline healthy and growing, confidently leading discovery through close, momentum building

6 months in: Multiple enterprise deals advancing through negotiation, forecasting reliable pipeline

12 months in: Closed 3-5 enterprise clients, established scalable sales approach for extended sales team

What You Bring

  • 5-7+ years selling HR tech, digital health, or workforce solutions to senior HR buyers
  • Track record closing complex enterprise deals to CHROs and Total Rewards leaders
  • Experience in pivot/expansion mode—you've taken early traction and built it into consistent revenue
  • Comfortable being the solo sales hire who doesn't need constant direction
  • Natural credibility with HR executives; you speak their language
  • Excited to shape a sales motion, not just execute someone else's playbook
  • Willingness to travel as needed

Why Work Here

  • Ownership of an entire market for an established company
  • Real infrastructure and support (Product, Marketing, Client Success, Leadership)
  • Direct partnership with CEO and deep advisor network on strategy
  • Excellent comp, strong benefits, mission-driven team
  • Room to grow into sales leadership as we scale

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