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Overwatch AI Raises $1.5M to Fix Airline Operations

Key Points
  • Overwatch AI raised $1.5 million in pre-seed funding to expand Wingman, its AI decision-support platform for airline operations teams.
  • The round included Baobab Ventures, United Airlines Ventures, Pegasus Airlines Innovation Lab, Masia, and aviation and AI angel investors.
  • Wingman is live across airlines handling 30,000 monthly flights, reporting 150 hours saved per team member and up to $4 million in annual savings.
May 20, 2026
Overwatch AI founders
Credits: Overwatch AI

Funding details

Overwatch AI, a startup that builds AI tools to help airlines manage flight operations, has raised $1.5 million in pre-seed funding. The round will go toward expanding the company's platform and signing up more airline customers. Overwatch AI was co-founded by Leo Kotil, a former commercial pilot with close to a decade of flying experience, and Nikita Kaeshko, who previously built applied AI products for the self-driving industry.

Flight delays cost money at a scale most people don't see. Industry analyses drawing on regulatory filings and economic studies estimate that disruptions cost U.S. aviation between $30 and $34 billion every year, a figure that researchers increasingly describe as a structural problem rather than a seasonal one. In 2024, U.S. carriers posted an on-time arrival rate of 78.10%, according to the Department of Transportation, meaning roughly one in five flights ran late. Independent analyses suggest performance deteriorated further at several major hubs through late 2024 and into early 2025. The core issue for airline staff is not a shortage of information. It is the time it takes to find the right piece of it, fast enough to matter.

The $1.5 million pre-seed round included Baobab Ventures and United Airlines Ventures, alongside Pegasus Airlines Innovation Lab and Masia, and a group of angel investors with backgrounds in AI infrastructure and aviation.

Why information management is such a difficult problem in aviation

Before a single flight, a pilot might need to check weather, NOTAMs (notices about airspace and airport conditions), fuel levels, runway status, maintenance records, and company procedures, each sitting in a different system with its own login and format. Dispatchers face the same challenge, but for hundreds of flights at once, while also tracking union agreements, airport curfews, and a stack of regulations.

Operations control centers have it worst. These are the teams responsible for keeping an entire airline's schedule running, and they are making time-sensitive decisions without a single unified picture of what is happening across the network. When something slips through, the result is a delay, a diversion, or a regulatory violation, all of which carry real costs.

Generic AI tools, the kind built for general use, are not well suited to this environment. They can produce plausible-sounding answers that turn out to be wrong, which is a serious problem when the stakes include passenger safety and regulatory compliance. Overwatch AI designed its platform for aviation specifically, with the requirement that every answer must be traceable back to an official document or live operational data.

How Overwatch AI plans to use the $1.5 million

The funding is earmarked for three things. The first is hiring, with the company looking to add engineers, product staff, and people with direct aviation experience. The second is expanding what the platform can do, adding integrations and covering more operational scenarios and user groups. The third is rolling out to additional airlines without losing the service quality the company says is essential for a product used in cockpits and control rooms.

The goal is broader coverage across the frontline. Overwatch AI wants Wingman to be useful for pilots, cabin crew, dispatchers, ground staff, and operations managers. With the product already running in live airline environments, the immediate focus is scaling what works rather than rebuilding the concept.

What Wingman does and how it works

Wingman is an AI platform that connects an airline's documents and operational data and makes all of it searchable through plain-language questions. A crew member or dispatcher can type a question in natural language, the way they would ask a colleague, and get an answer in seconds. Critically, every answer comes with a reference to the source material, so the person reading it can verify it immediately.

The platform works on mobile, tablet, and desktop, and is built to function in low-bandwidth environments, which matters in airports and on the ground where connectivity is not always reliable.

Overwatch AI says the platform is already running across multiple airlines that together handle more than 30,000 flights per month. From that live usage, the company reports 150 hours saved per team member per year, a 6.6% increase in overall crew productivity, a 4.6-fold improvement in compliant decision-making, and average annual savings of up to $4 million per airline.

The investors behind the round

This is the first disclosed funding round for Overwatch AI. The investor group covers both financial capital and operational knowledge of the industry.

Pegasus Airlines is involved as a customer, design partner, and investor, a combination that gave the Overwatch AI team access to real operational environments and direct feedback during development. United Airlines Ventures, the investment arm of one of the world's largest carriers, adds industry weight and, according to the company, a higher bar for what the product must be able to do.

Baobab Ventures is led by Carles Reina, an early-stage investor who has backed more than 70 companies, including ElevenLabs and Revolut. The fund focuses on AI, robotics, and defense. Masia rounds out the lineup as Overwatch AI's connection to the Barcelona startup ecosystem and beyond. The angel investors in the round bring experience in AI infrastructure and deploying technology in regulated industries.

Funding details

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