Forward Deployed Engineer

Chicago, Illinois

Alexander Chapman
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YC S'23 AI Startup Backed by A16Z & First Round

A rapidly growing, profitable startup is transforming the $900B freight logistics industry with voice AI agents - automating the 50+ phone calls, emails, and texts it takes to move a single truckload.


They're doing 7-figure ARR, growing 50% month-over-month, and used by many of the top 100 freight brokers nationwide.


Role: Forward Deployment Engineer

This is a hybrid engineering + operations role - perfect for someone who wants to own real-world deployments and work directly with customers.


Key Responsibilities:

  • Lead end-to-end deployment of AI agents
  • Triage issues, integrate systems, and ensure smooth rollouts
  • Act as technical POC for customers
  • Translate real-world feedback into product improvements
  • Build internal tools, docs, and onboarding workflows

Ideal Candidate:

  • Background in software/field engineering or technical consulting
  • Strong problem-solver in high-stakes, fast-moving environments
  • Comfortable working in production
  • Communicates well with both technical and non-technical teams
  • Based in Chicago or open to relocating
  • Thrives in early-stage, high-autonomy environments

Why Join:

  • Real product, real users, and rapid growth
  • Work directly on greenfield AI deployments
  • Small team of elite builders (ex-CTOs, Waymo, Meta, TikTok)
  • Huge opportunity for ownership and impact

Interested or know someone who'd be a great fit?

Reach out:

Date Posted: 02 May 2025
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