Senior Software Engineer

Chicago on site Until 8/21/2026 First posted March 27, 2026 Last posted March 27, 2026
Job description

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

About this role

Summary

Develop end-to-end features for customer-facing freight marketplace, working directly with users and stakeholders.

Job title

Senior Software Engineer

Experience level

4+ years

Industry

software

Location requirements

Chicago-based; remote work not specified.

Salary

Not specified

Management role

No

Skills & keywords

Required skills

typescriptsoftware developmentfull-stackownership

Preferred skills

None specified

Specializations

typescriptfull-stackcustomer-facingvoice agents
Locations

Structured locations inferred from the posting.

Chicago, IL, USA

On-site City