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Amazon Catalytic Capital

Account Executive with Freight Brokerage Experience

FleetWorks

FleetWorks

Sales & Business Development
Chicago, IL, USA
USD 100k-150k / year + Equity
Posted on Oct 14, 2025

Location

Chicago

Employment Type

Full time

Location Type

On-site

Department

Sales

Compensation

  • $100K – $150K • 0.01% – 0.1% • Offers Commission

Every year, companies spend over a trillion dollars moving freight across the U.S. — but the system for matching trucks with jobs is still slow, manual, and fragmented. FleetWorks is fixing that.

We’re building voice agents that transform the chaotic freight booking process into a modern, intelligent marketplace. Our agents replace the endless phone calls, texts, and emails and match truckers who want to get paid with loads that need to be moved. We've gone from 0 to $2m ARR in 8 months and we're just getting started.

Learn about our series A here!

The Role
We're looking for a high-impact Account Executive to help drive the next wave of FleetWorks’ growth. You’ll own the full sales cycle—from outbound to close—targeting top domestic freight brokerages. This role is ideal for a hungry, scrappy closer who thrives in fast-moving environments and knows how to break into complex accounts.

What You’ll Do

  • Own end-to-end sales for new freight brokerage customers

  • Prospect and qualify leads through cold outreach, LinkedIn, email, and industry events

  • Lead compelling product demos that show how FleetWorks unlocks real ROI

  • Navigate complex deals with multiple stakeholders, from operators to executives

  • Partner cross-functionally with Product and Customer Success to deliver a world-class onboarding experience

  • Maintain clean CRM hygiene and contribute to forecasting and pipeline strategy

What We’re Looking For

  • 4+ years of closing experience in freight tech

  • Existing relationships with freight brokerage clients

  • Strong track record of exceeding quota in outbound-heavy roles

  • Deep familiarity with the freight brokerage space

  • Comfortable selling technical products and communicating business value

  • Startup-minded: resourceful, proactive, and excited to build from 0→1

Compensation Range: $100K - $150K