# Senior Software Engineer - Forward Deployed

**Company:** [FleetWorks](https://hotfix.jobs/companies/fleetworks)
**Location:** Chicago, IL, San Francisco, CA
**Role:** Solutions Architecture
**Experience:** 3+ years
**Skills:** TypeScript, Node.js, REST APIs, AI Agents, Prompt Engineering, System Integration, Debugging, Production Systems
**Posted:** 2026-05-27

> Own end-to-end customer deployments of AI voice agents for freight logistics. Embed with operators in Chicago to build integrations, resolve live issues, and shape product roadmap based on real workflows.

## Job Description

## 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

## 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

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**Apply:** https://hotfix.jobs/jobs/cc752748-1de4-46b9-a146-056d97bcd564
**Canonical:** https://hotfix.jobs/jobs/cc752748-1de4-46b9-a146-056d97bcd564