Head of Employer Sales

Role Overview

• Own full-cycle enterprise sales to CHROs, HR Technology 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.

Requirements

• 5-7+ years selling HR tech, digital health, or workforce solutions to senior HR buyers
• Track record closing complex enterprise deals to CHROs, HR Technology 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

Benefits

• 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