Head of Sales – Brokerage (Player‑Coach)

About the role

We are a growing freight brokerage operating across all modes—truckload, LTL, drayage, and intermodal—seeking a player‑coach to build a repeatable sales motion from the ground up. You will sell from day one while designing the playbook, metrics, and eventually leading a sales team.

Key responsibilities

• Take a personal sales quota immediately, prospecting and closing new accounts across all freight modes.
• Develop the sales playbook, define ideal customer profiles, outreach approaches, and performance metrics.
• Collaborate with operations to ensure early wins are serviced well and retained.
• Identify and fix breakdowns in the current sales process.
• Recruit, hire, and coach additional salespeople once the playbook is proven.
• Set team quotas, conduct pipeline coaching, and report forecasts to leadership while staying on personal quota.

Required profile

• Proven hunter who builds business through cold or near‑cold outreach, not inbound leads.
• 3–5 years of freight brokerage sales experience with knowledge of TL, LTL, drayage, and intermodal.
• Ability to sell service, reliability, and relationships rather than price alone.
• Understanding of brokerage margins and ability to sell value without excessive discounting.
• Ready to coach and build a repeatable sales system, comfortable with ambiguity.

What we offer

• 50/50 base‑variable compensation structure.
• Base salary $90,000+ depending on experience.
• Variable commission tied to gross margin of new accounts, target equal to base at quota.
• On‑target earnings $180,000+ with uncapped upside.
• Remote work with flexibility to run your territory.