Andy Szybalski

sha · ’ball · ski

Designer and Engineer · andyszy@gmail.com · Honolulu

Founding designer of Google Street View, first designer on the project that became Waymo, co-founder of Uber Eats, co-founder of Cove AI which I designed and built from the first commit and which was acquihired by Microsoft in 2026. Now building new experiences at Microsoft and building a new school in Honolulu.

Experience

Partner Product Design Director · Microsoft AI

  • Building brand new AI experiences, continuing the work of Cove AI.

2026 — Present

Co-Founder & Board Chair · Tradewinds School

  • Founding Hawaiʻi’s first school designed for gifted minds (grades K–5), opening in Kaimukī in 2026.
  • Building Rabbithole, an open-source AI learning platform where students, teachers, and an AI thought partner explore ideas through Socratic dialogue and hands-on projects—activity management, generative mastery tracking, exploration seeds, and learner profiles.

2025 — Present

Co-Founder, Designer & Engineer · Cove

  • Co-founded a startup unlocking new ways for people to work together with AI; raised $6M from Sequoia Capital, Elad Gil, Homebrew, and other world-class investors.
  • Led design and built product end-to-end, from the first prototype to a launched app. Team acquired by Microsoft in 2026.

2023 — 2026

Design Advisor, Builder & Investor · Independent

  • Advised founders in the earliest stages of building their businesses. Highlights: Regrello (acq. Salesforce), Pepper (now Series C), Cottage (acq. RenoFi), Doorstead, Office Hours, Mighty Health, The Pill Club, Flexspace, and Flowly.
  • With a team of three, self-funded and built an AI powered travel booking tool called Osito. Booked some revenue, abandoned to work on Cove.
  • Launched an experimental generative music project.
  • Angel invested alongside Sequoia and Greylock.

2019 — 2024

Sr Director of Product Design, Uber Eats · Uber

  • On the founding team of Uber Eats; built from nothing into a $25B+ GMV business and a significant second line of business alongside rides.
  • Built and led an all-star design org in the era of large human teams—50+ product designers, researchers, and UX writers—across the eater, restaurant, and courier sides of the marketplace.

2014 — 2020

Staff User Experience Designer · Google

  • Founding designer of Street View, and the first designer on the self-driving car project (now Waymo).
  • Led design on early AI products in the pre-LLM era like Google Now and Schemer, and designed key parts of Google Earth and Google Maps.

2006 — 2014

Education

Stanford University — B.S. and M.S. Computer Science (with Honors and Distinction)

Earlier

  • GV — Entrepreneur in Residence (2014)
  • Apple — Software Engineering Intern, Final Cut Pro family; Objective-C (2005)
  • Firaxis Games — Software Engineering Intern, Sid Meier’s Civilization IV (2004)

Skills

Designing AI personalities · Shaping the editorial point of view of AI products · Product & interaction design · Zero-to-one product building · Prototyping & front-end engineering · AI product design