Roles › Senior Software Engineer
Chicago, IL
Senior Software Engineer jobs in Chicago, IL
10 open roles from 9 employers. Checked Oct 6, 2026.
What these openings look like
9 employers are hiring here: Caterpillar, DRW, Project44 and TransUnion. 6 of the 10 publish a pay range, running $78,750 to $250,000 a year. The rest do not say. Every posting is full time. The most recent went up on Oct 2, 2026.
Every listing links to the employer's own application. Nothing is posted here on their behalf, and nothing is reposted from anywhere else.
Open roles
Senior Software Engineer
Posted Oct 2 · Verified Oct 6
Senior Software Engineer
Posted Sep 30 · Verified Oct 6
Senior Software Engineer (Options)
Posted Sep 22 · Verified Oct 6
Senior Software Engineer
Posted Sep 21 · Verified Oct 6
Senior Software Engineer
Posted Sep 11 · Verified Oct 6
Senior Software Engineer
Posted Sep 3 · Verified Oct 6
Senior Software Engineer (Databricks Platform Engineer)
Posted Aug 17 · Verified Oct 5
Senior Software Engineer
Posted Aug 5 · Verified Oct 6
Senior Software Engineer
Posted Aug 4 · Verified Oct 6
Senior Software Engineer
Posted May 26 · Verified Oct 6
What it pays here
Only some employers publish a range. These are the ones that did, as written in their own postings:
- $112,710–$183,140 a year
- $175,000–$250,000 a year
- $78,750–$131,250 a year
- $80,000–$120,000 a year
- $102,400–$179,000 a year
What they ask senior software engineer candidates here
Drawn from the 10 open postings on this page. The ones that come up across several employers are near the top.
You'd help build a cloud-based Global Warranty Management solution replacing legacy systems. How would you approach migrating data and logic from an old system you didn't write?
What they are checking: Whether they plan for hidden business rules and data quality issues in legacy migrations.
Walk me through how you'd design an API that dealers use to submit warranty claims.
What they are checking: Whether they think about validation, idempotency, versioning and partner usability in a real integration.
Tell me about a time you worked through a large transformation on an Agile team. What made it hard?
What they are checking: Whether they can stay productive and steady through long programs with shifting requirements.
How do you make sure a cloud service stays reliable when dealers around the world depend on it?
What they are checking: Whether they think about monitoring, failover and graceful failure, not only features.
The business wants warranty data to drive product quality insights. How would you design the system so that data is usable for analytics?
What they are checking: Whether they design data models with downstream reporting and quality analysis in mind.
A product owner wants a feature fast, but you see it creating technical debt. What do you do?
What they are checking: Whether they can explain tradeoffs clearly and negotiate a path that serves both speed and quality.
Tell me about a code review where you pushed back on something. How did it go?
What they are checking: Whether they give useful feedback respectfully and raise team standards as a senior engineer.
How do you test a system that has a lot of complex business rules, like warranty eligibility?
What they are checking: Whether they use thoughtful automated testing so rule changes do not break existing behavior.
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