Account Executive - AI

FleetWorks • Chicago, IL

1d

About The Position

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're working with some of the biggest brokers in the country and building fast.
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. As one of our early hires on the sales team, 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.

Requirements

• 4+ years of closing experience (freight-tech experience is great but not required!)
• Strong track record of exceeding quota in outbound-heavy roles
• Comfortable selling technical products and communicating business value
• Startup-minded: resourceful, proactive, and excited to build from 0→1

Responsibilities

• 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

Benefits

• Top tier cash and equity compensation—we aim to be above 75th %ile for companies who have raised a similar amount of cash
• Competitive medical, dental, and vision benefits
• Fully covered lunches and dinners
• The opportunity to learn quickly, grow fast, and be rewarded for your contributions

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Education Level: No Education Listed
• Number of Employees: 1-10 employees