Senior Software Engineer - Forward Deployed
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Key skills for this role
Key Skills for This Role
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What You’ll Do:
Own customer deployments end-to-end, from initial scoping to integration design to production rollout.
Work directly with customer operators and leaders to understand real workflows, pain points, and edge cases, translating them into clear, high-quality technical solutions.
Build production features and integrations that allow our AI agents to operate inside complex customer environments.
Diagnose and resolve issues in the field, often in real time and with incomplete information, owning outcomes all the way through.
Travel 20–30% to customer sites nationwide to unblock deployments, map operational processes, and ensure successful go-lives.
Collaborate closely with product and core engineering to shape the roadmap based on what you observe directly on the ground.
Develop tools and reusable workflows that improve deployment speed and reduce friction for future customers.
Operate with extreme ownership, ensuring customers experience immediate and measurable value from our platform.
What we look for:
- 3–6+ years of professional software engineering experience, with clear ownership of complex, production-critical systems.
- Strong command of TypeScript, Node.js, and REST API design, including debugging and integrating with external systems.
- Hands-on experience with AI-driven systems, including tuning agent behavior, refining prompts, and shaping workflow logic based on customer feedback.
- Exceptional communication and judgment, especially when balancing speed, reliability, and real-world constraints.
- 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
About FleetWorks
Automates freight brokerage operations using AI voice and email agents.
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