Pilot (pilotplans.com)

Pilot is multiplayer consumer AI for travel: the free web & mobile app where groups plan, decide, & book trips together

  • Stage $1M in TTM Revenue
  • Industry Travel
  • Location San Francisco, CA, USA
  • Currency USD
  • Founded September 2021
  • Employees 10
  • Incorporation Type Other
  • Website pilotplans.com

Company Summary

Multiplayer consumer AI for travel: groups plan, decide, & book trips together. Founded by a 3x founder w/ a $30M bootstrapped SaaS exit and early travel unicorn experience. Now centralizing everything needed to make trips happen in one place, and with it the intent and group data needed to power AI that incumbent OTAs covet but weren’t built for. Went from ~pre-rev to US$1.51M gross booking run rate in 8mo on just $13K in spend. CA$2.2M raised.

Team

  • Founder, CEO

    Connor Wilson has worked in and around travel his whole career, from his first job at a hotel and an early role at a travel unicorn, to bootstrapping a marketing-software company (NiceJob) that served the travel industry to a $30M exit in 2021. He’s been a startup growth leader (his core discipline) for over 12 years: the same instinct took Pilot to a $1.51M run rate on roughly ~$13K of ad spend. He was also VP Growth at a $90mil/yr Fintech.

  • Co-Founder, Head of Product

    Yu-Wei Hung leads technical product across web and mobile, spanning end to end from design through shipped code. He built Pilot's LLM-powered data pipelines and the recommendation systems that turn a planned trip into a booking, and led the product work that secured 3.2M merchant-of-record listings and Pilot's technical approval into Google Travel.

  • Avinash VK
    Co-Founder, Head of Engineering

    Avinash built the initial core platform and runs engineering. He took Pilot from the first prototypes to a live product across web, iOS, and Android, built the hotel booking engine it monetizes through, and owns the data infrastructure and back-end the AI runs on. He has been building software for over 10 years, since his teens, with published IEEE research on transformer-based summarization.

Advisors

Previous Investors

  • AngelList Quant Fund
    Unconfirmed
    Next Canada (via Ajay Agrawal, Founder of Creative Destruction Lab, & Reza Satchu, Senior Lecturer at Harvard Business School)
    Unconfirmed
    RealTech Capital Group
    Unconfirmed
  • TMR Capital
    Unconfirmed
    Edward Chiang (Founder of Moment Energy, $116M raised)
    Unconfirmed
    Neil Wainwright (Founder of Nexonia, $100M+ exit)
    Unconfirmed
  • Tosh Rayadhurgam (User who loved Pilot so much he invested $70k)
    Unconfirmed
    Almost every former teammate who worked with Connor at NiceJob
    Unconfirmed
    Grant Sorensen, ex-Palantir (Enterprise Execution Lead), Office of the President at Etched
    Unconfirmed

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