Head of Sales

We’re looking for a Head of Sales to lead and scale JOON’s growing sales organization.

This is a strategic, high-impact role for a player-coach who can own the full sales motion while laying the foundation for future growth. You’ll refine our go-to-market playbook, build repeatable systems, and lead by example through hands-on execution and mentorship.

You’ll work closely with the founders and cross-functional leaders to accelerate JOON’s next stage of growth, driving expansion across the HR tech, wellness, and employee benefits ecosystem. You’ll have significant ownership, a direct line to leadership, and the opportunity to help shape the company’s long-term sales culture and strategy.

What You’ll Do

• Lead and build the sales team — setting direction, process, and performance standards.
• Own the full sales cycle from outreach to close.
• Refine and optimize our sales systems, pipeline management, and reporting for predictable growth.
• Develop scalable sales playbooks and enablement resources that can grow with the team.
• Collaborate cross-functionally with marketing, product, and customer success to ensure alignment across the buyer journey.
• Expand strategic partnerships within the HR, benefits, and PEO ecosystem.
• Analyze performance metrics to identify trends, improve efficiency, and drive continuous improvement.
• Work directly with the founders on revenue goals, GTM strategy, and long-term sales planning.

Who You Are

• 7+ years of B2B SaaS sales experience, with at least 3+ years in a leadership capacity.
• Proven track record of driving growth and closing deals with HR, People, or Benefits leaders.
• Experienced with consultative, solution-based sales and comfortable leading by example.
• A self-starter who thrives in dynamic environments and knows how to be scrappy when needed.
• Adept at building structure and systems while keeping a hands-on approach.
• Comfortable using HubSpot, AmpleMarket, and other modern sales platforms to manage pipeline, outreach, sequences, and performance data.
• Highly collaborative and data-driven with a focus on consistent execution.
• Passionate about employee wellbeing, HR tech, and creating meaningful impact.
• Excited to lead a mission-driven team and help take an established product to its next level of scale.