Account Executive - AI Agents
FleetWorks
Location
Chicago; San Francisco
Employment Type
Full time
Location Type
On-site
Department
Sales
Compensation
- The listed OTE range is based on SMB and mid-market coverage. For candidates with enterprise experience, compensation is structured to reflect that level of scope and complexity. We're happy to discuss details during the process. $180K – $220K • Offers Equity
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