[Hiring] Head of Sales, Brokerage @CloudTrucks

Role Description

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. This role exists because we need someone who can build a repeatable sales motion from scratch.

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 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 ensure 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 sales effort is breaking down and fix it.
  • Collaborate with account management to ensure new accounts are handed off cleanly and retained.
• As We Scale — Coach & Hire
  • Recruit and hire additional salespeople once the playbook is proven.
  • Coach and develop the sales team — ride-alongs, deal reviews, pipeline coaching.
  • Set team quotas and hold people accountable to them.
  • Report on pipeline, forecast, and performance to leadership.
  • Stay on a personal quota even as the team grows — this is a player-coach role indefinitely.

Qualifications

• You are a Hunter.
• You have built a book of business from cold or near-cold outreach.
• You are comfortable picking up the phone, walking into a shipper’s office, and building a relationship over time.
• You have closed freight accounts where the pitch was ‘trust us, we’ll take care of you’.
• You know how to sell service, reliability, and relationships — not just price.
• You have real freight experience.
• You have sold freight brokerage services and understand modes, lanes, carrier relationships, and shipper needs.
• You can speak credibly about TL, LTL, drayage, and intermodal to a transportation manager or VP of logistics.
• You understand how margin works in brokerage and can sell value without giving away the deal.
• You have at least 3–5 years of freight brokerage sales experience.
• You can coach and build.
• You have either managed salespeople before, or you are clearly ready to.
• You are a systems thinker.
• You give honest feedback and hold people accountable without burning relationships.
• You are comfortable with ambiguity.
• You are wired for this environment.
• You thrive in a smaller, scrappier organization where you have real ownership and real impact.
• You do not need a large support infrastructure to be effective.
• You manage your own time, hit your own deadlines, and don’t wait to be told what to do.
• You want to be compensated based on what you produce.

Compensation

• This role is structured as a 50/50 base and variable split.
• Base Salary: $90,000+ depending on experience.
• Variable: Commission on new accounts you bring in — target variable equal to base at quota.
• OTE: $180,000+ at quota. Uncapped above that.
• Commission is tied to the gross margin generated by accounts you personally bring in.

Why This Role

• You will have direct access to company leadership and real influence over how the sales org is built.
• There is no ceiling — if you build it well, you lead it.
• You will not be selling a commodity at a company with 10,000 other salespeople.
• The operational foundation is real — you will not be selling something we cannot deliver.
• Remote with flexibility to run your territory the way you need to.