hirly

Fleetworks

Senior Software Engineer

Chicago

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Role family
Engineering
Seniority
Senior
Country
US
Work mode
On-site / unstated
First seen by hirly
10 Sept 2026

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the posting

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 have a small, high-agency team working out of our offices in SF and Chicago. As an early engineer, you will be a true owner of your work, developing features end to end, interacting directly with our customers, and shaping our culture.

Learn about our series A here !

What you'll do

Own end-to-end feature development, working directly with a high-ownership team including our founders, customers, and other engineers

Make product and technical decisions that will shape the future of FleetWorks

Ship new work every day

Learn from others and teach those around you

What we look for

Professional experience owning end-to-end feature development on customer-facing products

At least 4 years of professional full-time software development, including at least one 2 years or more at one company (or a company and its acquirer)

Comfort working in our stack or picking it up quickly—we use TypeScript across the stack

A healthy appreciation for hard problems—we already handle tens of thousands of phone calls and emails per day and we’re just getting started

Empathy for your users and your colleagues

How we'll get to know each other

Quick call with Megan, our Talent lead, for you to share your goals and motivations, what you’ve worked on that you’re proud of and to figure out together how that might fit in with what we’re working on at FleetWorks

45-min live-coding interview with an engineer who you'll work with if you join, so that we can get to know how you think about technical challenges

Paid onsite work trial so that we can get to know how you work and you can get to know us

Well talk with your references to help us understand how to best support your development at work—we might do this after you've signed your offer

Transparent offer process that clearly outlines how we came to the compensation package we’re offering, including the current and potential value of your equity

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

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Senior Software Engineer at Fleetworks — hirly