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

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

Remote, United States | Full-time | Nationwide territory

$110,000-$120,000 base | Approximately $220,000 target OTE, with stretch potential around $240,000

Your first Head of Sales seat

Ready to lead a sales function without stepping away from selling? This private-equity-backed driver-safety and training company has more than 3,000 customers and a new recurring-revenue platform. You will report directly to company leadership and build its first repeatable outbound engine. For a strong performer, the role can grow toward VP of Sales or CRO scope as the business scales.

You will carry an individual quota of approximately $300,000-$400,000 while coaching a junior AE and working with SDR support. A second AE is planned. The role starts close to a 50/50 selling/coaching split and should move toward 40/60 as the team grows. You will have existing market insights and training materials, but real freedom to build the playbook.

The sales motion

Outbound calls and emails drive most new business, with some conference leads. Junior sellers handle faster, higher-volume deals averaging about $2,000 in annual contract value; your own mid-market deals average around $10,000, with occasional larger opportunities. Buyers include fleet, safety, training, operations, EMS, fire, and local-government leaders. You will receive SDR support but still generate your own pipeline.

What you'll do

• Personally prospect, run discovery, and close new and recurring-revenue business.
• Coach junior sellers through call reviews, deal strategy, and direct feedback.
• Build practical messaging, cadences, pipeline standards, and forecasts; help grow the team.

What you'll bring

• 5+ years of full-cycle B2B sales, recent personal quota ownership, and clear performance evidence.
• Experience creating outbound pipeline and repeatedly closing SMB or mid-market deals, not only large enterprise contracts.
• Experience managing or meaningfully coaching an SDR, BDR, or junior seller while staying hands-on.
• Comfort building in a lean organization, college education, and willingness to travel selectively.

Fleet, public safety, local government, LMS, EdTech, safety, compliance, or training-software experience helps, but the right sales motion matters more than an exact industry match.

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.