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.

Role Snapshot

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Location: Remote within the United States

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Territory: Nationwide U.S.

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Employment Type: Full-time

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Compensation: $110,000–$120,000 base salary with a 50/50 split; target OTE around $220,000, with stretch potential around $240,000

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Travel: As needed for industry events, trade shows, and key customer meetings

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Team Scope: Lead and coach a small sales team, including junior sellers and SDR support

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Individual Quota: Expected around $300,000–$400,000

What You Will Own

Carry and Close Your Own Book

- Build a nationwide pipeline across public-sector and commercial accounts.

- Prospect, qualify, run discovery, navigate stakeholders, and close new business.

- Sell safety training, compliance, and software-enabled training solutions into EMS, fire, fleet, logistics, warehouse, transportation, and related environments.

- Manage deal sizes that commonly range from $5,000–$20,000, with larger opportunities reaching roughly $75,000 and some government deals requiring longer procurement cycles.

- Engage buyers ranging from day-to-day safety and training operators to fleet executives, finance leaders, and other senior stakeholders.

- Develop partnerships with insurance, risk, safety, membership, and industry organizations.

- Represent the company at trade shows and industry events.

Coach and Build the Sales Team

- Coach junior AEs and SDR-level talent through call reviews, deal strategy, shadowing, and timely feedback.

- Help sellers improve qualification, objection handling, stakeholder mapping, follow-up, and close strategy.

- Support recovery plans for stalled deals and complex multi-stakeholder opportunities.

- Create a practical sales playbook, operating cadence, scripts, messaging, and repeatable process.

- Keep HubSpot clean, accurate, and useful for forecasting and team visibility.

- Report pipeline, forecast, and revenue progress to executive leadership.

- Help hire and onboard future sellers as the function grows.

What Makes You a Strong Fit

- You have 5+ years of Account Executive or sales leadership experience in public-sector, government-adjacent, commercial SaaS, training, compliance, fleet, transportation, safety, risk, or another transferable B2B environment.

- You have owned complex, multi-stakeholder sales cycles and can show evidence of creating pipeline, advancing deals, and closing business.

- You have directly managed or meaningfully coached BDRs, SDRs, junior AEs, or early-career sales talent.

- You are still energized by selling yourself—not just inspecting someone else’s forecast.

- You know how to operate in a small-team, resource-conscious environment where the playbook i