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

About the role

This is a high‑visibility, player‑coach position leading growth for a long‑established, private‑equity‑backed safety‑training and software company. You will sell directly into public‑sector and commercial fleet environments while building the sales process, cadence, and team capability needed to scale recurring revenue nationwide.

Key responsibilities

• Own and close a personal sales book targeting EMS, fire, logistics, warehouse, school bus, and other vehicle‑intensive customers.
• Build a nationwide pipeline across public‑sector and commercial accounts, managing deal sizes from $5,000 to $75,000 and larger government contracts.
• Develop and nurture partnerships with insurance, risk, safety, and industry associations.
• Represent the company at trade shows, industry events, and key customer meetings.
• Lead, coach, and mentor a small sales team of junior sellers and SDRs, improving their prospecting, qualification, and closing skills.

Required profile

• Proven track record of meeting or exceeding sales quotas in B2B environments.
• Experience selling safety, compliance, or training solutions to fleet‑focused organizations.
• Strong ability to navigate complex stakeholder groups, including operations, finance, and executive leadership.
• Demonstrated coaching or leadership experience, preferably with junior sales talent.

Required skills

What we offer

• Base salary $110,000–$120,000 with a 50/50 split and target OTE around $220,000 (stretch to $240,000).
• Remote work within the United States, with travel as needed for events and key meetings.
• Opportunity to shape the go‑to‑market engine and build a repeatable sales motion for a growing company.