Why we started Overwatch AI

Jun 1, 2025

What do airline pilots and utility field workers have in common?

Background

Leo and I met through the YC community in 2023 and quickly developed an interest in each other’s “tech stacks”. 

Leo was a commercial pilot turned aviation software innovation director, while I was working on self-driving products in the Valley. 

We both operated at the intersection where software meets real-world operations, and we noticed a huge gap between how we did our work and how frontline folks managed their knowledge and tasks.

Leo experienced this firsthand while flying commercial airliners, dealing with over 12,000 pages of flight manuals and checklists on a regular basis. Quite demanding for any modern human.

I observed a similar challenge when rolling out self-driving tech for major enterprises in the U.S. Frontline workers were drowning under intense performance expectations and overwhelming stacks of procedural documentation.

Problem

We realised that unlike folks in sales, marketing, or back-office roles, these frontline professionals can’t just whip out their phones and use AI to simplify their work. Or can they?

After having 70+ customer conversations we discovered there is a need for a frontline AI Copilot that can:

  • Work offline, since connectivity is not stable

  • Be tailored to their industry, understand the complexity of a specialized environments

  • Keep sensitive company data on-prem or on-device

In early 2025, we founded Overwatch AI to build exactly that. Our first goal is to put an on-demand 10-year veteran in every frontline worker's pocket whenever they're stuck navigating a complicated manual or a tricky situation.

Vision

Our vision doesn’t stop there. As we deploy AI to frontline workers, we’ll also capture the critical “how things are really done in the physical world” knowledge. Over time, the AI models will evolve into proactive AI sidekicks for every frontline professional. Initially, as an AI copilot on device, and eventually as an embodied AI working alongside the most skilled experts in the field.

Now let's get to work.