Head OF Sales

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 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

Who You Are

You are a Hunter

• 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 Real Freight Experience

• 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 Can Coach and Build

• 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 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 — not just what you’re paid to show up

Compensation

This role is structured as a 50/50 base and variable split. We want you to have real skin in the game, and we want the upside to reflect the value you create.

Component

Structure

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.

Variable structure:

Commission is tied to the gross margin generated by accounts you personally bring in. The more you build, the more you earn — and that income stream continues as accounts are retained. We will work through the specifics with the right candidate.

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. Your wins will matter.

• 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

About CloudTrucks

CloudTrucks is a virtual trucking carrier in the multi-billion dollar trucking space. Core to this industry are over 3.5M truck drivers. They move more than 70% of all goods transported around the U.S., yet operate in a highly fragmented industry with huge opportunities for products, services and automation. We strive to deliver solutions that help truck drivers operate with much greater efficiency, increase their revenue, and offload business complexity. We are looking for uniquely exceptional people to join us on our journey as we massively scale into an industry-defining business.

We provide equal employment opportunities to all employees and applicants for employment and prohibits discrimination and harassment of any type without regard to race, color, religion, age, sex, national origin, disability status, genetics, protected veteran status, sexual orientation, gender identity or expression, or any other characteristic protected by federal, state or local laws.