Startups

Head of Sales, Brokerage (CTX)

Cloudtrucks · Remote · Remote

← All jobs
About Cloudtrucks

CloudTrucks is a new way to manage your trucking business. Maximize revenue and minimize headaches with technology-driven products that give you everything you need to make the most of your trucking business. Backed by Menlo.

About the role

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.

What they're looking for

  • You have built a book of business from cold or near-cold outreach — not from inheriting accounts or riding inbound leads at a large broker
  • 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’ — not ‘here’s our brand recognition’
  • You know how to sell service, reliability, and relationships — not just price
  • You have sold freight brokerage services — you 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
More about this role

Player-Coach | All Modes | Remote

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.

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

Read the full posting on Cloudtrucks's site ↗

Sales

Build your edge while you search

Free tools for founders and investors, plus VC Unfiltered, our take on startups, venture and the people who build them.