Customer Support Engineer

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. Fleet Works is fixing that.

We’re building AI voice and email 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 hiring a Founding Support Engineer to build Fleet Works’ technical support function from the ground up. You’ll be the front line of defense for our customers—triaging issues, debugging across our stack, resolving tickets independently, and creating the run-books and processes that will scale as we grow. This is a 0-to-1 role based in Chicago, with focus on supporting our EST and CST customers.

Learn about our series A here!

• Own first-line technical support for Fleet Works’ customers—diagnosing issues across AI agent logic, data, integrations, and configuration without needing an engineer to hand-hold you
• Build the support engineering function from scratch: ticketing workflows, triage criteria, escalation paths, runbooks for known issues, and documentation standards
• Resolve 80%+ of routine technical tickets independently within your first 90 days.
• Handle day-to-day configuration changes, API Health Monitoring, agent behavior updates (prompting, routing rules, and call/email flows), compliance policy settings, and standard integration setup for customers and partners
• Communicate directly with customers’ technical teams to troubleshoot and test integrations, translating complex issues into clear, actionable language for both technical and non-technical stakeholders
• Surface patterns and recurring issues to Product and Engineering so that common problems get permanently fixed in the product rather than repeatedly triaged

• 3+ years of professional experience in a technical support, support engineering, or similar hands‑on debugging role
• Strong debugging instincts—you can take a vague report like “the agent isn’t working right” and systematically narrow it to root cause across application logic, data, integrations, and configuration
• Comfort reading logs, navigating APIs, and working across cloud infrastructure without needing hand‑holding
• Experience communicating with both technical and non‑technical audiences—you can write a bug report that Engineering can act on immediately and explain an issue to an operations manager in plain language
• 0-to-1 builder experience and mindset—you thrive in ambiguity, create structure where none exists, and feel ownership over building processes, not just following them
• High agency—you see what needs to be done and do it, surface the state of things proactively, and handle urgent issues when freight is moving and customers need you
• Curiosity about freight and logistics—you’re eager to learn loads, rates, TMS integrations, and the operational context that makes support issues time‑sensitive

• Quick call with Megan, our Recruiter, for you to share your background, what draws you to support engineering at an early‑stage startup, and to figure out together how that might fit in with what we’re building at Fleet Works
• 90‑minute take‑home exercise: a realistic debugging scenario where you’ll analyze logs, write a root cause analysis, make an escalation decision, and draft customer communications—no Leet Code, just the actual work
• 45‑minute technical interview with an engineer to walk through your debugging approach and how you think about triage and escalation
• Onsite interview where you’ll triage simulated support tickets, diagnose issues, and present your findings—so we can see how you work and you can get to know us
• We’ll 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

• 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
• The opportunity to build a critical function from the ground up at a high‑growth startup
• The opportunity to learn quickly, grow fast, and be rewarded for your contributions