Built by airline operations practitioners
Founded in 2023, Tailsight grew from years spent seeing regional fleets lose revenue when maintenance coordination failed and better data could have prevented it.
Keep aircraft flying on schedule
Regional airlines operate on tight margins. A surprise grounding, missed maintenance window, or parts shortage that could have been anticipated earlier carries an outsized cost at this scale.
We built Tailsight for this segment because existing planning tools serve large flag carriers with dedicated planning teams. Regional operators need the same intelligence with a fraction of the complexity and cost.
The gap we are closing
Scheduling maintenance for a 15 to 50 aircraft fleet is hard. Regulatory deadlines, flight assignments, and parts inventory sit in separate systems, while planners coordinate them with spreadsheets and calendar reminders.
That coordination gap creates AOG events. An AD deadline slips because a busy flying weekend hides the conflict. A parts order misses its window because the planner does not know a component is nearing its limit.
Tailsight reads all three sources at once and shows planners what their spreadsheet misses.
Team
James works across airline operations and maintenance planning. He founded Tailsight to address scheduling gaps that ground smaller operators and leads commercial and customer work.
Tom builds data integration systems for operationally intensive work. At Tailsight, he designs the connector layer and engineering infrastructure, including links to MRO and flight-ops systems.
Priya has worked on operational data problems in transportation and logistics. At Tailsight, she leads product and customer onboarding, shaping workflows around how maintenance planners actually work.
How we work
We start with a planner's real problem. We meet customers, observe planners, and see how decisions happen before we build.
We do not claim support for systems we have not tested. If your MRO setup is not reliable for us, we tell you before you commit.
AI assists, it does not replace planners. They can override every recommendation, and each decision is logged for a complete audit trail.
Boston headquarters
Tailsight, Inc. was incorporated in 2023 and is based in Boston, MA. We work closely with early access operators on maintenance scheduling.