About Us

Healthee is on a mission to make access to a healthier life effortless.. With rapid growth and exciting milestones behind us, including a successful Series A and $12M ARR, we're continuing to build a world-class team. We're looking for a passionate, entrepreneurial Sales Director to take ownership of broker and mid-market sales, leading by example as both a front-line manager and a player-coach until the team scales.

Role Overview

We’re looking for a dynamic Sales Manager to lead and grow our Broker and Mid-Market Sales teams. Initially, you’ll manage one sales rep while driving your own deals. You will play a crucial role as a player-coach—actively participating in sales efforts while building out the team. As the organization grows, your focus will evolve from executing deals to scaling, managing, and coaching a larger team. This position will report directly to our VP of Sales.

Key Responsibilities

• Lead and Manage: Manage and mentor a small team, providing day-to-day support, training, and guidance.
• Player-Coach: Close your own deals while guiding the team to exceed quotas and deliver results.
• Team Growth & Hiring: Attract, interview, and onboard top sales talent to scale the team effectively.
• Sales Strategy & Execution: Develop and implement sales strategies to drive growth in the broker and mid-market segments.
• Performance Management: Track key performance metrics, analyze trends, and ensure the team hits revenue targets.
• Forecasting & Reporting: Collaborate with the VP of Sales to provide accurate forecasts and communicate progress to executive leadership.
• Cross-Functional Collaboration: Work closely with Marketing, Product, and Customer Success teams to ensure alignment and optimize the customer journey.
• Process Optimization: Establish scalable processes and best practices to increase efficiency and productivity across the sales organization.

What We’re Looking For

• 5-8+ years of experience in B2B sales, with at least 2 years managing and scaling teams.
• Experience selling to brokers or mid-market clients in the health, benefits, or Human Capital SaaS space is a plus.
• Demonstrated success as a player-coach—capable of closing deals while developing a team.
• Strong leadership and coaching skills to motivate and inspire a growing team.
• Proven ability to hit or exceed revenue targets and manage sales pipelines effectively.
• Hands-on, entrepreneurial spirit with a willingness to roll up your sleeves.
• Excellent communication and collaboration skills, with the ability to thrive in a cross-functional environment.
• Data-driven approach to managing sales operations, forecasting, and decision-making.
• Strong preference for leaders who have used the MEDDPICC process
•  High change orientation is required in a company that is scaling as quickly as we are
• Process-oriented

Why Join Us?

• We grew in excess of 10x in 2024.
• We already have the business sold to minimally double in 2025.
• A unique opportunity to build and scale a sales team from the ground up.
• Competitive compensation package with performance bonuses and equity options.
• Comprehensive benefits package (PTO, health, and wellness offerings).
• A culture that values resilience, personal growth, and work-life balance.
• The plan if for the role and responsibilities of this position to quickly expand
• In only 3 years in the market, we have thousands of business clients and hundreds of thousands of eligible users
• Opportunity to get equity in a rapidly scaling SAAS AI-driven company

Benefits

• Health Care Plan (Medical, Dental & Vision)
• 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
• Hybrid Work
• Wellness Resources
• Stock Option Plan

Salary:

We welcome candidates with varying levels of experience for this role, which is reflected in the flexible salary range. The final salary will be determined through an assessment during the interview process, in line with our internal development levels. 

For New York City-based hires: Compensation Range: 175K-200K base salary, subject to standard withholding and applicable taxes. In addition to base salary, the role includes the opportunity to receive commissions and equity based on the Company’s plans and in accordance with the Company’s policies. Compensation finally awarded to the candidate will be commensurate with the candidate’s skills and experience. Compensation ranges for candidates in locations outside of New York City may differ based on the cost of labor and such additional factors for such other locations.