Founding Forward Deployed Engineer / Integrations

TrueMile is the operating layer for mid-market trucking carriers.

We build AI agents that run day-to-day operations: sourcing and planning loads, assigning them to drivers, handling driver and broker communications, and replanning in real time when something changes. This is the work that keeps a fleet moving, and we are building the system that does it around the clock.

Our founder grew up in a family trucking business and ran a fleet before starting TrueMile. That background shapes everything we build. We understand how carriers actually operate, what breaks in the yard, and what a dispatcher's day really looks like. We build alongside carriers as live design partners, so the product stays grounded in real operations.

Where we are:

• Backed by Y Combinator.
• Live with real fleets, with seven figures in contracted revenue.
• Early, growing fast, and building the foundation of the company right now.

Why you would want to be here:

• Real ownership from day one. You own meaningful parts of the product, and your work goes live with real operators the same week you ship it.
• Hard, tangible problems worth solving. The agents make real operational decisions for real trucking businesses.
• A small team with high standards that moves fast and cares about the work and the operators we build for.

If you want to build software that operators depend on every day, we would love to talk.

TrueMile builds AI agents that run day-to-day operations for mid-market trucking carriers. This role owns the last mile between a signed pilot and a fleet running on TrueMile in production.

You will sit with carriers, wire TrueMile into the systems they already run, tune the agents against live fleet data, and turn pilots into production. It is the highest-leverage seat at the company. Nothing ships to a customer without you.

What you will own:

• Carrier go-lives end to end, from kickoff to live in the yard.

• Integrations with the ELDs, TMS, and telematics systems carriers run every day.

• Tuning the agents against real fleet data so they make the right calls in production.

• The first-line technical relationship with customers. You find the real pain and turn it into shipped fixes.

• The playbook that makes every future go-live faster.

You might be a fit if:

• You have done hard technical work at a startup or big tech, founded something, or obsess over projects you have shipped and kept live.

• You are comfortable in front of customers and can turn a messy operational problem into a clear plan.

• You ship fast, finish what you start, and care that it keeps working.

• You can learn a complex industry quickly. Trucking experience is a plus, not a requirement.

• You are comfortable with Python and TypeScript.

Stack: TypeScript and Python, LLM-driven agents, a cloud-native backend. Modern and pragmatic. We optimize for reliable systems that operators depend on, not novelty.

This is an in-office role in San Francisco. If you want to build software that real operators rely on, let's talk.

We build reliable AI agents on top of real operational data. The interesting problems sit at the intersection of language models, real-time systems, and messy real-world logistics data.

A few of the challenges:

• Getting agents to make consequential operational decisions reliably, with the right checks in place.
• Integrating with the systems carriers already run, and making sense of inconsistent real-world data.
• Real-time operations: conditions change constantly, and the system has to keep up.

Our stack is modern and pragmatic: TypeScript and Python, LLMs, and a cloud-native backend. We care more about shipping reliable systems than chasing novelty.