Sales Director, Enterprise

Location: New York / Remote
 Reports to: VP of Sales
 Role Type: Full-time

About Healthee

At Healthee, our mission is simple: to make access to a healthier life effortless. In just three years, we’ve achieved rapid growth, including a successful Series B, thousands of business clients, and hundreds of thousands of users. As we continue to scale our AI-driven SaaS platform, we’re looking for an entrepreneurial Sales Director to lead and grow our Enterprise sales team.

Role Overview

This is a unique opportunity to build and scale an enterprise sales team from the ground up. Initially managing 2–3 sales reps with the plan to build the headcount as business demands, you will be directly participating in your team's deals while coaching and mentoring your team. Reporting to the VP of Sales, you’ll shape strategy, refine processes, and drive results in a fast-paced, high-growth environment.

What You’ll Do

• Lead & Manage: Inspire and develop a small, high-performing team through hands-on coaching, training, and support.
  
   
• Team Growth: Attract, hire, and onboard top talent to expand the team as the company scales.
  
   
• Sales Strategy & Execution: Develop and implement strategies to grow our enterprise customer base.
  
   
• Performance Management: Monitor key metrics, analyze trends, and meet targets.
  
   
• Forecasting & Reporting: Deliver accurate forecasts and communicate progress to executive leadership.
  
   
• Cross-Functional Collaboration: Partner with Marketing, Product, and Customer Success to align on goals and optimize the customer journey.
  
   
• Process Optimization: Establish scalable sales processes and best practices to drive efficiency and effectiveness.
  
   

What We’re Looking For

• 5–8+ years of B2B sales experience, with at least 3 years managing and scaling teams.
  
   
• Proven success selling to enterprise clients, ideally in health, benefits, or Human Capital SaaS.
  
   
• Strong leadership and coaching skills to motivate and grow a team.
  
   
• Demonstrated ability to exceed revenue targets and effectively manage pipelines.
  
   
• Hands-on, entrepreneurial mindset with a willingness to travel to clients and conferences.
  
   
• Excellent communicator and collaborator, thriving in a cross-functional environment.
  
   
• Data-driven, process-oriented, and experienced in managing sales operations and forecasting.
  
   
• Familiarity with MEDDPICC methodology strongly preferred.
  
   
• Comfortable navigating change and ambiguity in a fast-scaling organization.
  
   

Why Join Us?

• Opportunity to build and scale a sales team in a rapidly growing, AI-driven SaaS company.
  
   
• Competitive compensation, including performance bonuses, equity, and comprehensive benefits.
  
   
• A culture that values resilience, personal growth, and work-life balance.
  
   
• Clear path for the role and responsibilities to expand quickly as we grow.
  
   

Benefits

• Medical, dental & vision plans
  
   
• Retirement plan (401k, IRA)
  
   
• Life insurance (basic, voluntary & AD&D)
  
   
• Paid time off (vacation, sick & public holidays)
  
   
• Family leave (maternity & paternity)
  
   
• Short-term & long-term disability
  
   
• Training & development resources
  
   
• Hybrid work options
  
   
• Wellness programs
  
   
• Stock option plan
  
   

Compensation

For New York City-based hires: Base salary range of $200K, plus commissions and equity, commensurate with experience and skills.
For candidates in other locations, compensation may vary based on market factors.
We are committed to pay equity and transparency and will assess final compensation during the interview process in alignment with internal development levels and our commitment to fairness.