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

• 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

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 is still being built.
• You are comfortable selling to practical operators as well as executive and finance stakeholders.
• You can work effectively in a remote environment with strong discipline around follow-through, CRM hygiene, and communication.
• You have a bachelor's degree or equivalent college education.

Backgrounds That May Transfer Well

You do not need to come from one exact industry to be credible here. Strong fits may come from environments such as:

• Public sector, local government, or government-adjacent sales
• Fleet, transportation, logistics, delivery, warehouse, or vehicle-intensive operations
• EMS, fire, emergency services, or public safety markets
• Safety, compliance, workforce training, or certification-based solutions
• Vertical SaaS or recurring-revenue products sold into operational teams
• Insurance, risk management, brokers, associations, or member organizations

Why This Role Is Different

This is not a large-company sales management role where every process, enablement asset, and resource already exists. It is a builder role for someone who wants ownership.

You will have the chance to influence the sales motion at a company with an established customer base, a real market need, upgraded technology, and executive attention on growth. For the right person, this can be a step toward broader sales leadership as the team scales.

Compensation The base salary range is $110,000-$120,000 annually, with a 50/50 base-variable structure and target OTE around $220,000.

At Urrly, fairness matters. We use AI to review every application against the same clear requirements for the role. Candidates are evaluated only on job-related factors such as skills, certifications, and experience, not personal attributes.

Apply now and get a response within 24 hours.