Head of Sales (Player-Coach)
New
U
UrrlyFleet Safety Training
Remote within the United StatesFull-TimeManager
Salary$110,000–$120,000 base salary with a 50/50 split; target OTE around $220,000, with stretch potential around $240,000
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Job Details
- Experience
- 5+ years
- Required Skills
- Stakeholder managementHubSpotCRM
Requirements
- 5+ years of Account Executive or sales leadership experience in B2B environments such as public sector, SaaS, compliance, fleet, or safety.
- Proven experience owning complex, multi-stakeholder sales cycles.
- Direct experience managing or coaching BDRs, SDRs, or junior AEs.
- Experience operating in a small-team, resource-conscious environment where processes are being built.
- Strong CRM hygiene discipline, specifically using HubSpot.
- Bachelor's degree or equivalent college education.
- Ability to travel for industry events and key customer meetings.
- Comfort selling to a broad range of stakeholders from day-to-day operators to fleet and finance executives.
Responsibilities
- Build a nationwide pipeline across public-sector and commercial accounts.
- Prospect, qualify, manage discovery, and close new business for safety training and software-enabled solutions.
- Coach junior AEs and SDRs through call reviews, deal strategy, and timely feedback.
- Develop a practical sales playbook, operating cadence, scripts, and repeatable processes.
- Maintain HubSpot data for accurate forecasting and team visibility.
- Report pipeline, revenue progress, and forecasts to executive leadership.
- Represent the company at trade shows and industry events.
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