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.