[Hiring] Head of Sales (Player-Coach) @Urrly

Role Description

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 includes:

• 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.

Qualifications

• 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.

Requirements

• 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.

Benefits

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

Company Description

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.