Remote Player-Coach Head of Sales — Fleet Safety Training

Remote Genie; Northern (KY); Hybrid; USD 110,000 - 120,000; Full time

Job summary

Urrly is seeking a Head of Sales (Player-Coach) to lead national growth in fleet-safety training and software. You will own a substantial book, coach junior sellers, and design a scalable go-to-market engine while closing new business directly.

This is a hands-on leadership role with a strong personal quota and the freedom to shape processes, cadence, and partnerships with industry groups. Remote within the United States, you’ll manage a nationwide territory and build a high-performance team.

Qualifications

• 5+ years of AE or sales-leadership experience in public-sector, SaaS, or safety/training.
• Owned multi-stakeholder deals and built pipeline and close strategy.
• Experience coaching junior sellers and creating repeatable processes.

Responsibilities

• Build a nationwide pipeline across public-sector and commercial accounts.
• Prospect, qualify, run discovery, navigate stakeholders, and close.
• Sell safety training and software-enabled training solutions.
• Manage deal sizes from $5K–$20K, with larger opportunities up to $75K.
• Engage buyers from operators to executives and finance leaders.
• Represent the company at trade shows and industry events.
• Keep CRM clean and forecast-ready.

Skills

Account Executive experience

Sales leadership

Public-sector sales

SaaS sales

Remote selling

Education

Bachelor's degree

Tools

HubSpot

Job description

Urrly is seeking a Head of Sales (Player-Coach) to lead national growth in fleet-safety training and software. You will own a substantial book, coach junior sellers, and design a scalable go-to-market engine while closing new business directly.

This is a hands-on leadership role with a strong personal quota and the freedom to shape processes, cadence, and partnerships with industry groups. Remote within the United States, you’ll manage a nationwide territory and build a high-performance team.