Senior Software Engineer
FleetWorks
Chicago, IL · Posted May 27, 2026
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Where Chicago, IL ranks
Where Chicago, IL placed in our monthly rankings, month by month. Each month stays online at its own address.
November 2026
- #1Best cities for government pay after cost of living$146k · of 18
- #1Cities with the most jobs that do not need a four-year degree in the Midwest684 jobs · of 51
- #1Cities with the most jobs that do not need a four-year degree in the Great Lakes684 jobs · of 36
- #1Best cities for software and engineering jobs in the Midwest1,140 openings · of 59
- #1Best cities for software and engineering jobs in the Great Lakes1,140 openings · of 48
- #1Best all-round cities for mid-career professionals in the Midwest80 / 100 · of 20
Rankings about engineering jobs
- Best cities for software and engineering jobs #1 San Francisco (3,412 openings)
- Best cities for engineering pay after cost of living #1 San Mateo ($216k)
- Most requested AI skills in engineering jobs #1 AI tools in daily work (6.1%)
- AI tools named most often in engineering jobs #1 Claude (1.7%)
- Employers with the most engineering jobs #1 Amazon (2,992 roles)
Pay compared with the market
This listing does not state pay. Across 1,097 open senior software engineer listings that state pay, the middle half runs $170,000 to $222,500 and the median is $200,000.
Listed pay is what employers advertise, not what people are paid.
Senior Software Engineer salaries by state · Check your own pay
How AI is used in this kind of work
Among software developers, AI is already used for some of the tasks. Measured exposure for software developers: 29% (some).
Share of this job’s tasks that AI is already used for at work, from real usage. It is not a forecast of job loss, and a low number means no use seen yet. Source: Anthropic Economic Index.
Skills this job asks for
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About the job
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 products that transform the chaotic freight booking process into a modern, intelligent, agentic 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 office in SOMA. 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.
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 3 years of professional full-time software development experience
- Comfort working in our stack or picking it up quickly, we use TypeScript across the stack
- A healthy appreciation for hard problems, we orchestrate thousands of agents and are 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
- 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