Head of Sales, Brokerage (CTX)

CloudTrucks • San Francisco, CA

10d • Remote

About The Position

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. 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.

Requirements

• 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
• 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, ideally some of it at a smaller or mid-size shop where you had to figure things out yourself
• You have either managed salespeople before, or you are clearly ready to — you can articulate how you would develop someone
• You are a systems thinker: you don’t just want to sell, you want to build something repeatable
• You give honest feedback and hold people accountable without burning relationships
• You are comfortable with ambiguity — there is no polished playbook waiting for you. You are writing it.
• 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 — not just what you’re paid to show up

Responsibilities

• 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
• 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
• 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

Benefits

• 50/50 base and variable split
• 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
• Direct access to company leadership and real influence over how the sales org is built
• Opportunity to lead the sales organization if built well
• Wins will matter
• 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

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Education Level: No Education Listed