F
fleetworksvia Ashby
Senior Account Executive
ChicagoPosted 1mo ago
OtherSeniorFull-time#ai-lab
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About the Role
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 https://www.fleetworks.ai/blog/fleetworks-launches-always-on-dispatcher-for-trucking-industry-with-17m-funding!
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 (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 in San Francisco 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
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 https://www.fleetworks.ai/blog/fleetworks-launches-always-on-dispatcher-for-trucking-industry-with-17m-funding!
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 (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 in San Francisco 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
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