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This Ex-Pilot Is Building AI for the Cockpit
Aviation safety depends on having the right information at the right moment. The problem is that the information is fragmented, voluminous, and hard to retrieve when no flight is entirely the same. In non-standard situations, crews aren’t short on rules—they’re short on time to find and verify the one that matters.
Leo Kotil built Overwatch AI after spending a decade in the cockpit and airline operations. His bet is simple: GenAI is most valuable in aviation when it turns manuals, NOTAMs, and operational data into fast, source-backed answers that crews can verify—and still use when connectivity drops.
This conversation examines where AI belongs in flight operations. Not in decision authority, but in compressing the time from a non-standard situation to the verified reference that governs it without breaking the safety model that makes aviation work.
What You’ll Learn
- Why aviation’s real bottleneck is retrieval, not knowledge: The documents exist; the problem is locating the right section fast enough when the situation isn’t standard.
- How “digital” still leaves crews doing manual search work: iPads and PDFs replaced paper, but many workflows still rely on folder navigation and keyword search.
- What makes an AI assistant usable in regulated ops: Answers must surface the exact source passages so pilots and frontline teams can confirm and trust the output.
- Why context is the product, not a nice add-on: Pulling in live and structured data (weather, aeronautical publications, flight context) removes extra steps and reduces mistakes.
- How multilingual reality changes system design: Crews ask in their native language while documents stay in English, often mixing aviation terms—retrieval has to handle that reliably.
- How startups ship into aviation within a regulated environment: Deploy as a supplemental layer on top of existing certified tools, then prove value before becoming “core.”
- Why offline capability is mandatory: Aviation software needs a usable fallback when connectivity is unavailable, not just a degraded mode in theory.
- The tradeoffs of using proprietary LLM APIs in airlines: Provider dependency, infrastructure variability, and sensitive data processing create risks beyond normal cloud hosting.
Time-Stamped Highlights
- (00:20) From Airline Pilot to Aviation Founder
- (01:08) Career Path Across Airline and Business Aviation
- (03:01) The Operational Reality of a Pilot’s Day
- (05:54) Pre-Flight Procedures and Checklist Pressure
- (09:10) EFBs, Manuals, and Information Overload
- (12:12) Founding Overwatch AI and Meeting a Co-Founder
- (13:56) Early Traction and the Techstars Accelerator
- (15:41) Networks, Credibility, and Selling Into Airlines
- (20:04) Designing an AI Assistant for Frontline Ops
- (21:29) Native Language, Voice Input, and Real Usage
- (23:01) Regulatory Constraints and Compliance Strategy
- (27:01) Product Roadmap and Near-Term Focus
- (29:09) Contextual Data as the Core Differentiator
- (37:39) Offline AI, Edge Constraints, and Aviation Grade
- (40:52) Model Lock-In, APIs, and Enterprise Risk Tradeoffs
Guest
Leo Kotil — Founder and CEO, Overwatch AI
Leo is the co-founder and CEO of Overwatch AI, where he is building AI systems to support pilots, cabin crew, operations control centers (OCC), and ground staff in managing flight disruptions and non-standard operations. A former airline pilot, he brings firsthand experience of aviation frontline workflows and operational decision-making into the design of practical, regulation-aware AI tools for airlines.
LinkedIn: https://www.linkedin.com/in/leo-kotil/
Company: https://overwatch-ai.com/
About the Podcast
Travel Tech Podcast features long-form conversations with leaders across travel and technology. The show explores how software, data, operations, and distribution come together in real businesses, with an emphasis on tradeoffs, incentives, and lessons that transfer beyond any single company or role.
Host
Alex Brooker — Founder, Airside Labs
Alex is an engineer, technology leader, and founder with deep expertise in mission-critical systems and AI oversight. He leads Airside Labs, an AI business that applies aviation-grade testing and compliance rigor to enterprise AI systems, helping organizations build and test AI agents in regulated environments. Before founding Airside Labs, Alex built and scaled complex software in aviation and safety-critical domains, blending product innovation with disciplined engineering practices. He also invests in early-stage technology ventures and advocates for thoughtful, real-world AI deployment strategies.
LinkedIn: https://www.linkedin.com/in/alex-brooker-2280002/
Links & References
- EASA (European Union Aviation Safety Agency): https://www.easa.europa.eu/
- Electronic Flight Bag (EFB): https://www.easa.europa.eu/en/domains/operations/electronic-flight-bag-efb
- NOTAMs (Notices to Air Missions): https://www.icao.int/airnavigation/information-management/notams/Pages/default.aspx
Brought To You By
Airside Labs — Airside Labs supports aviation and travel operators with tools to test, deploy, and scale modern data and AI systems in safety-critical environments. Learn more at https://airsidelabs.com.
View all episodes
By Airside LabsAviation safety depends on having the right information at the right moment. The problem is that the information is fragmented, voluminous, and hard to retrieve when no flight is entirely the same. In non-standard situations, crews aren’t short on rules—they’re short on time to find and verify the one that matters.
Leo Kotil built Overwatch AI after spending a decade in the cockpit and airline operations. His bet is simple: GenAI is most valuable in aviation when it turns manuals, NOTAMs, and operational data into fast, source-backed answers that crews can verify—and still use when connectivity drops.
This conversation examines where AI belongs in flight operations. Not in decision authority, but in compressing the time from a non-standard situation to the verified reference that governs it without breaking the safety model that makes aviation work.
What You’ll Learn
- Why aviation’s real bottleneck is retrieval, not knowledge: The documents exist; the problem is locating the right section fast enough when the situation isn’t standard.
- How “digital” still leaves crews doing manual search work: iPads and PDFs replaced paper, but many workflows still rely on folder navigation and keyword search.
- What makes an AI assistant usable in regulated ops: Answers must surface the exact source passages so pilots and frontline teams can confirm and trust the output.
- Why context is the product, not a nice add-on: Pulling in live and structured data (weather, aeronautical publications, flight context) removes extra steps and reduces mistakes.
- How multilingual reality changes system design: Crews ask in their native language while documents stay in English, often mixing aviation terms—retrieval has to handle that reliably.
- How startups ship into aviation within a regulated environment: Deploy as a supplemental layer on top of existing certified tools, then prove value before becoming “core.”
- Why offline capability is mandatory: Aviation software needs a usable fallback when connectivity is unavailable, not just a degraded mode in theory.
- The tradeoffs of using proprietary LLM APIs in airlines: Provider dependency, infrastructure variability, and sensitive data processing create risks beyond normal cloud hosting.
Time-Stamped Highlights
- (00:20) From Airline Pilot to Aviation Founder
- (01:08) Career Path Across Airline and Business Aviation
- (03:01) The Operational Reality of a Pilot’s Day
- (05:54) Pre-Flight Procedures and Checklist Pressure
- (09:10) EFBs, Manuals, and Information Overload
- (12:12) Founding Overwatch AI and Meeting a Co-Founder
- (13:56) Early Traction and the Techstars Accelerator
- (15:41) Networks, Credibility, and Selling Into Airlines
- (20:04) Designing an AI Assistant for Frontline Ops
- (21:29) Native Language, Voice Input, and Real Usage
- (23:01) Regulatory Constraints and Compliance Strategy
- (27:01) Product Roadmap and Near-Term Focus
- (29:09) Contextual Data as the Core Differentiator
- (37:39) Offline AI, Edge Constraints, and Aviation Grade
- (40:52) Model Lock-In, APIs, and Enterprise Risk Tradeoffs
Guest
Leo Kotil — Founder and CEO, Overwatch AI
Leo is the co-founder and CEO of Overwatch AI, where he is building AI systems to support pilots, cabin crew, operations control centers (OCC), and ground staff in managing flight disruptions and non-standard operations. A former airline pilot, he brings firsthand experience of aviation frontline workflows and operational decision-making into the design of practical, regulation-aware AI tools for airlines.
LinkedIn: https://www.linkedin.com/in/leo-kotil/
Company: https://overwatch-ai.com/
About the Podcast
Travel Tech Podcast features long-form conversations with leaders across travel and technology. The show explores how software, data, operations, and distribution come together in real businesses, with an emphasis on tradeoffs, incentives, and lessons that transfer beyond any single company or role.
Host
Alex Brooker — Founder, Airside Labs
Alex is an engineer, technology leader, and founder with deep expertise in mission-critical systems and AI oversight. He leads Airside Labs, an AI business that applies aviation-grade testing and compliance rigor to enterprise AI systems, helping organizations build and test AI agents in regulated environments. Before founding Airside Labs, Alex built and scaled complex software in aviation and safety-critical domains, blending product innovation with disciplined engineering practices. He also invests in early-stage technology ventures and advocates for thoughtful, real-world AI deployment strategies.
LinkedIn: https://www.linkedin.com/in/alex-brooker-2280002/
Links & References
- EASA (European Union Aviation Safety Agency): https://www.easa.europa.eu/
- Electronic Flight Bag (EFB): https://www.easa.europa.eu/en/domains/operations/electronic-flight-bag-efb
- NOTAMs (Notices to Air Missions): https://www.icao.int/airnavigation/information-management/notams/Pages/default.aspx
Brought To You By
Airside Labs — Airside Labs supports aviation and travel operators with tools to test, deploy, and scale modern data and AI systems in safety-critical environments. Learn more at https://airsidelabs.com.