Demo

Account Executive - AI

FleetWorks
Chicago, IL Full Time
POSTED ON 4/14/2026
AVAILABLE BEFORE 5/8/2026
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.

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 (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

What we offer

  • 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

Compensation Range: $180K - $220K

Salary : $180,000 - $220,000

If your compensation planning software is too rigid to deploy winning incentive strategies, it’s time to find an adaptable solution. Compensation Planning
Enhance your organization's compensation strategy with salary data sets that HR and team managers can use to pay your staff right. Surveys & Data Sets

What is the career path for a Account Executive - AI?

Sign up to receive alerts about other jobs on the Account Executive - AI career path by checking the boxes next to the positions that interest you.
Income Estimation: 
$109,535 - $156,850
Income Estimation: 
$168,296 - $226,155
Income Estimation: 
$103,275 - $152,386
Income Estimation: 
$55,240 - $79,001
Income Estimation: 
$104,545 - $161,038
Employees: Get a Salary Increase
View Core, Job Family, and Industry Job Skills and Competency Data for more than 15,000 Job Titles Skills Library

Job openings at FleetWorks

  • FleetWorks Chicago, IL
  • 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, an... more
  • 14 Days Ago

  • FleetWorks Chicago, IL
  • 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, an... more
  • 14 Days Ago

  • FleetWorks San Francisco, CA
  • 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, an... more
  • 14 Days Ago

  • FleetWorks Chicago, IL
  • 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, an... more
  • 4 Days Ago


Not the job you're looking for? Here are some other Account Executive - AI jobs in the Chicago, IL area that may be a better fit.

  • Eightfold AI Chicago, IL
  • About Eightfold AI Eightfold was founded with a vision to solve for employment in our society. For decades, the connection between individuals and opportun... more
  • 23 Days Ago

  • FleetWorks Chicago, IL
  • 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, an... more
  • 4 Days Ago

AI Assistant is available now!

Feel free to start your new journey!