Head of Sales; Player-Coach Fleet Safety Training

Head of Sales (Player-Coach) – Fleet Safety Training

If you are a hands-on sales builder who still wants to carry a number, coach rising sellers, and shape the go-to-market engine—not just inherit someone else’s playbook—this is a high-visibility opportunity to lead growth for a long-established, PE-backed safety training and software company. You’ll sell directly into public-sector and commercial fleet environments while building the process, cadence, and team capability needed to scale recurring revenue nationwide.

The Opportunity This company has served safety-focused organizations for decades and supports more than 3,000 active customers across commercial fleets, state and local government, EMS, fire departments, logistics, warehouses, school bus operators, and other vehicle-intensive environments. Following a recent private-equity acquisition, the business has upgraded its technology and launched a recurring training platform designed for larger fleets. Now the company is ready to expand new-customer growth, increase share of wallet, and build a more repeatable sales motion.

This role is part seller, part coach, and part architect: you’ll own meaningful revenue directly while helping junior sellers improve how they prospect, qualify, navigate stakeholders, and close.

• Location:
  
  Remote within the United States
• Territory:
  Nationwide U.S.
• Employment Type:
  
  Full-time
• Compensation: $110,000–$120,000 base salary with a 50⁄50 split; target OTE around $220,000, with stretch potential around $240,000
• Travel:
  As needed for industry events, trade shows, and key customer meetings
• Team Scope:
  Lead and coach a small sales team, including junior sellers and SDR support
• Individual Quota:
  Expected around $300,000–$400,000

• Build a nationwide pipeline across public-sector and commercial accounts.
• Prospect, qualify, run discovery, navigate stakeholders, and close new business.
• Sell safety training, compl