Head of Sales

About the role

This private‑equity‑backed driver‑safety and training company serves over 3,000 customers and has launched a new recurring‑revenue platform. You will report directly to company leadership and build its first repeatable outbound engine while carrying an individual quota of approximately $300,000‑$400,000. The role starts with a roughly 50/50 split between selling and coaching a junior AE (with SDR support) and should evolve toward a 40/60 split as the team grows. You will have existing market insights and training materials but the freedom to develop the sales playbook.

Responsibilities

• 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.
• Generate your own pipeline while leveraging SDR support.
• Execute outbound calls and emails as the primary driver of new business, supplemented by conference leads.

Requirements

• 5+ years of full‑cycle B2B sales with recent personal quota ownership and clear performance evidence.
• Proven ability to create outbound pipeline and repeatedly close SMB or mid‑market deals (not solely large enterprise contracts).
• Experience managing or meaningfully coaching an SDR, BDR, or junior seller while remaining hands‑on.
• Comfort operating in a lean, fast‑moving organization.
• College education.
• Willingness to travel selectively.
• Background in fleet, public safety, local government, LMS, EdTech, safety, compliance, or training‑software is a plus but not required; the right sales motion matters most.

Pay

Base salary $110,000‑$120,000; target OTE approximately $220,000 with stretch potential around $240,000.

Schedule

Full‑time, remote position with a nationwide territory.