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

Urrly • Tallahassee, FL

58d • Remote

About The Position

This is a high-visibility opportunity to lead growth for a long-established, PE-backed safety training and software company. The role involves selling directly into public-sector and commercial fleet environments while building the process, cadence, and team capability needed to scale recurring revenue nationwide. The company has served safety-focused organizations for decades and supports over 3,000 active customers. Following a recent private-equity acquisition, the business has upgraded its technology and launched a recurring training platform designed for larger fleets, and is now 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, owning meaningful revenue directly while helping junior sellers improve their sales skills.

Requirements

• 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.
• Experience owning complex, multi-stakeholder sales cycles with evidence of creating pipeline, advancing deals, and closing business.
• Directly managed or meaningfully coached BDRs, SDRs, junior AEs, or early-career sales talent.
• Energized by selling yourself, not just inspecting forecasts.
• Experience operating in a small-team, resource-conscious environment where the playbook is still being built.
• Comfortable selling to practical operators as well as executive and finance stakeholders.
• Ability to work effectively in a remote environment with strong discipline around follow-through, CRM hygiene, and communication.
• Bachelor’s degree or equivalent college education.

Nice To Haves

• Backgrounds from public sector, local government, or government-adjacent sales.
• Experience in fleet, transportation, logistics, delivery, warehouse, or vehicle-intensive operations.
• Experience in EMS, fire, emergency services, or public safety markets.
• Experience with safety, compliance, workforce training, or certification-based solutions.
• Experience with vertical SaaS or recurring-revenue products sold into operational teams.
• Experience in insurance, risk management, brokers, associations, or member organizations.

Responsibilities

• Carry and close your own book of business.
• 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.
• Manage deal sizes ranging from $5,000–$20,000, with larger opportunities reaching roughly $75,000.
• 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 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.

Benefits

• Base salary range: $110,000–$120,000 annually.
• 50/50 base-variable compensation structure.
• Target OTE around $220,000, with stretch potential around $240,000.
• Remote within the United States.
• Travel as needed for industry events, trade shows, and key customer meetings.
• Opportunity to influence the sales motion at a company with an established customer base, a real market need, upgraded technology, and executive attention on growth.
• Potential step toward broader sales leadership as the team scales.

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level