Head of Sales, Brokerage (CTX)

Head of Sales, Brokerage (CTX)

Player-Coach | All Modes | Remote

The Opportunity

We are a growing freight brokerage operating across all modes — truckload, LTL, drayage, and intermodal. We move freight for real customers, we have a solid operational foundation, and we are ready to grow. What we have not yet cracked is a repeatable sales motion.

This role exists because we need someone who can build that motion from scratch — not inherit a brand, not manage a team that already exists, but come in, sell, figure out what works, and then scale it. That means you will be carrying a bag yourself while simultaneously developing the system, the playbook, and eventually the team that makes us a sales-driven company.

This is not a role for someone who needs a big logo behind them to open doors. It is a role for someone who is good enough at selling to win without one.

What this is not: If your track record is built on inbound leads at a large national broker, a recognized brand, this is probably not the right fit. We need someone who knows how to build relationships and close business on the strength of service and hustle, not name recognition.

What You Will Do

In the First 90 Days — Sell

• Take over active prospecting immediately. You will carry a personal quota from day one.

• Identify the most winnable customer segments for our business and develop a target account list

• Build relationships through outbound — cold calls, warm introductions, in-person visits where it matters

• Close new accounts across any mode we can service: TL, LTL, drayage, intermodal

• Work closely with our operations team to make sure early wins are serviced well and retained

Ongoing — Build

• Develop the sales playbook: ideal customer profile, outreach approach, pitch, objection handling, and close process

• Define what ‘good’ looks like for a salesperson at this company — activity metrics, pipeline standards, conversion benchmarks

• Identify where our current...