Overwatch AI
Techstars '25Barcelona, ES · Founded 2024 · 5 employees on LinkedIn · 6 known investors
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Overwatch AI develops AI tools for airline operations. The company applies machine learning to support frontline aviation challenges.
Also known as Overwatch AI Corp.
Founders & leadership
Overwatch AI was founded in 2024 by Nikita Kaeshko.

Investors · 6
How we know: Masia's portfolio page · research · techstars.com · open dataset · 5k.vc investor directory · Not right? Tell us
How we know: Techstars's portfolio page · the Techstars portfolio · open dataset · Top 3000 Accelerator Startups (no YC) 2026-08 · open dataset · 5k.vc investor directory · Not right? Tell us
How we know: funding news · research · techstars.com · Not right? Tell us
Also in the syndicate · 3
Funding
SEC filings, press & company announcements$3.2M disclosed across 2 rounds · 2025–2026
- $1.5MPre-SeedMay 2026 · 3 sources
Alex Brooker, Baobab Ventures, David Bennett, Masia, Pegasus Innovation Lab, United Airlines Ventures
Source ↗
▶$1.7MraisedSep 2026 · 12 investors · OtherRule 506(b)
- Leo KotilExecutive Officer, Director
- Nikita KaeshkoDirector
- Offering amount
- $1.7M
- Amount sold
- $1.7M
- First sale
- Aug 2025
- Incorporated
- Corporation, Delaware, 2024
- Federal exemptions
- 06b
Source: SEC EDGAR Form D. Amounts as filed; amended filings shown once at their latest values.
Company profile
researched Sep 2026Overwatch AI is an aviation technology company that develops an AI-based operational intelligence and decision-support platform for airlines. Its product, Wingman, ingests and unifies airline data sources — including operating manuals, maintenance and aircraft records, flight data and external feeds such as weather and NOTAMs — and makes them queryable in natural language so that pilots, cabin crew, ground and ramp staff and operations control centre teams can retrieve information relevant to technical issues, airport and airline requirements, and weather assessments. Answers are grounded in official documentation or data and sourced, and the platform includes continuous automated evaluations intended to detect hallucinations and non-compliance.
The platform is distributed across mobile, tablet and desktop, including for low-bandwidth environments, and provides managers with analytics on knowledge gaps, compliance and return on investment. The company positions the product around reducing the time frontline aviation workers spend searching across fragmented legacy systems, which it describes as more than 30 minutes per shift on average. It is headquartered in Barcelona, Spain, and reports live use across multiple airlines.
Founding story
Co-founders Leo Kotil, a commercial airline pilot who moved into aviation software innovation, and Nikita Kaeshko, a technology entrepreneur who worked on self-driving products in the United States, met through the Y Combinator community in 2023. Kotil's experience navigating over 12,000 pages of flight manuals and checklists, and Kaeshko's observation of frontline workers in enterprise self-driving deployments struggling with procedural documentation, led them to identify a shared problem. After more than 70 customer conversations they concluded frontline professionals needed an AI copilot that works offline, is tailored to their industry and keeps sensitive data on-premises or on-device, and founded the company in 2025 to build it.
Business model
Overwatch AI sells its Wingman platform to airlines as enterprise software, deploying it to frontline operational teams and airline management, with security-oriented deployment that leaves customers in control of proprietary data. Company materials also reference on-premises or on-device handling of sensitive company data.
Traction
The platform is in live use across multiple airlines, supporting more than 30,000 flights per month. Reported outcomes include 6.6% crew productivity increase, a 4.6x increase in compliant decision-making, roughly 150 hours saved per team member per year and up to $4M in annual savings per airline on average, as well as a stated 10x annual ROI and 53% higher accuracy than generic AI. Pegasus Airlines has begun using the platform in its operations.
Latest developments
In May 2026 Overwatch AI closed a $1.5M pre-seed round from United Airlines Ventures, Baobab Ventures, Pegasus Innovation Lab and Masia, plus angel investors David Bennett and Alex Brooker, to be used to grow the team, expand platform capabilities and roll out to additional airline customers. In the same month Pegasus Airlines announced its collaboration with the company and that it had begun using the platform operationally.
▸Full profile — market position, technology, go-to-market, geography, history, risks & controversies
Market position
Overwatch AI positions itself as an aviation-specific alternative to general-purpose assistants such as ChatGPT or Copilot, claiming higher accuracy on airline operational questions than generic AI. It reports use across multiple airlines and more than 30,000 flight operations per month, and counts United Airlines Ventures and Pegasus Innovation Lab among its backers.
Domain specialisation in aviation operations, answers grounded in and traceable to official airline documentation and data, continuous automated evaluation for accuracy and compliance, offline and low-bandwidth deployment for frontline environments, and customer control over proprietary data.
Technology
Wingman is a full-stack AI platform combining data ingestion and unification of unstructured and structured aviation data (manuals, maintenance records, flight data, weather and NOTAM APIs), a natural-language query interface with sourced answers grounded in official documentation, automated continuous evaluation and monitoring against public and proprietary benchmarks to mitigate hallucination and non-compliance risk, multi-device distribution including low-bandwidth environments, and analytics for managers. The founders have described a design goal of offline operation and keeping sensitive customer data on-premises or on-device.
Go-to-market
The company markets directly to airlines through demo requests on its website and works with airline innovation arms; Pegasus Innovation Lab, the Silicon Valley-based innovation unit of Pegasus Airlines, both collaborates with the company and participated in its pre-seed round. It also participated in Techstars (2025 class), whose startup spotlight channel covered the company.
Airlines and their frontline and operational staff: pilots and flight crew, cabin crew, maintenance engineers, ground and ramp operations personnel, and operations control centre (OCC) and operations managers.
Geography
Headquartered in Barcelona, Spain, with airline deployments described as global; the company works with Türkiye-based Pegasus Airlines via its Silicon Valley-based Pegasus Innovation Lab.
History
The company was founded in 2025 by Leo Kotil and Nikita Kaeshko (Techstars 2025 class) and published its founding rationale in a June 2025 blog post. In May 2026 it announced a $1.5M pre-seed round and Pegasus Airlines publicly disclosed a collaboration under which it had begun using the platform in operations.
Risks & controversies
Published performance figures — including productivity gains, compliance improvements, ROI and annual savings — originate from the company and its funding announcement rather than independent verification. Third-party aggregator listings for the round differ from primary reporting on amount and location, and the company name overlaps with unrelated businesses using "Overwatch".
Compiled by commissioned research from 9 cited public sources — announcements, filings, and press listed under research sources below.
Key figures
latest reportedCompany-reported or press-reported figures, each dated to when it was claimed — not independently audited.
Related companies · 4
Companies working in the same space as Overwatch AI.
Timeline · 2
launches, deals, and filingsPegasus Innovation Lab, the Silicon Valley-based innovation unit of Pegasus Airlines, announced a collaboration with Overwatch AI, and Pegasus stated it had begun actively using the natural-language operations platform within its operations.
Overwatch AI announced a $1.5M pre-seed round backed by United Airlines Ventures, Baobab Ventures, Pegasus Innovation Lab and Masia, with angel investors David Bennett and Alex Brooker. Proceeds are earmarked for team growth, expanding operational platform capabilities and deployments with additional airlines.
$1.5M source ↗
Dated company events from announcements, filings, and press; legal rows summarize public dockets and regulator releases.
In the news
▸Research sources · 9
primary sources listed
- Overwatch AIoverwatch-ai.com · web
9 public sources were cited for this profile; the first-party ones are listed here.
Frequently asked questions
- What does Overwatch AI do?
- Overwatch AI builds Wingman, an AI decision-support platform for airline operations and frontline aviation teams.
- Who founded Overwatch AI?
- Overwatch AI was founded by Nikita Kaeshko in 2024.
- Who are Overwatch AI's investors?
- Overwatch AI's investors include Masia, Techstars, Baobab Ventures.
- How much funding has Overwatch AI raised?
- Overwatch AI has disclosed $3.2M raised across 2 rounds.
- Where is Overwatch AI headquartered?
- Overwatch AI is headquartered in Barcelona, ES.





