Customer Support Engineer

FleetWorks • Chicago, IL

1d

About The Position

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 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 our first Support Engineer to build FleetWorks’ 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 runbooks and processes that will scale as we grow. This is a 0-to-1 role based in Chicago or SF, working core hours of 8 AM–5 PM CT.
Learn about our series A here!

Requirements

• 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
• A 0-to-1 builder 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

Responsibilities

• Own first-line technical support for FleetWorks’ 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, freeing our Forward Deployed Engineers to focus on complex TMS connectivity, API field mapping, and data flow architecture
• Handle day-to-day configuration changes, API key updates, agent phrasing adjustments, 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

Benefits

• 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

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Education Level: No Education Listed