Senior Software Development Engineer Jobs in Chicago, IL

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’re expanding our engineering team in Chicago, a major hub for our customers and the heart of U.S. freight operations. In this role, you’ll be a full member of our core engineering team, but deployed directly into the environments where our product meets the real world. You’ll build production features, design integrations inside messy customer systems, and shape the internal tooling and platform components that allow us to scale deployments efficiently.

If you’re a strong software engineer who wants to work hands-on with users, solve ambiguous problems on the ground, and see your code driving live operations within days, this is a uniquely high-leverage role.

Learn about our Series A here!

What You’ll Do:

• Lead technical delivery for customer implementations, integrations, and workflow builds; owning projects from scoping through production rollout.

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  Architect and build workflows that encode real customer processes, integrating directly with their systems and adapting to operational edge cases you uncover in the field.

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  Develop core platform components and integration tooling that standardize common patterns, reduce one-off work, and help the team scale customer deployments efficiently.

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  Navigate complex environments, fragmented data, and real-world constraints, and design solutions that work in practice, not just on paper.

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  Provide field insight to product and engineering, shaping the roadmap with firsthand customer understanding.

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  Travel 20–30% to customer locations and work in-person from our Chicago office.

What we look for:

• 3–6+ years of professional software engineering experience, with clear ownership of complex, production-critical systems.

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  Strong command of TypeScript, Node.js, and REST API design, including debugging and integrating with external systems.

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  Hands-on experience with AI-driven systems, including tuning agent behavior, refining prompts, and shaping workflow logic based on customer feedback.

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  Exceptional communication and judgment, especially when balancing speed, reliability, and real-world constraints.

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  Based in Chicago with willingness to travel 20–30% to customer sites.

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