# Jessica McKellar

> Jessica McKellar is the CEO of Pilot.com, the largest accounting firm for startups in the US, which she co-founded in 2017 alongside longtime collaborators Waseem Daher and Jeff Arnold. A MIT computer science alumna, she previously co-founded Zulip (acquired by Dropbox) and served as Director of Engineering at Dropbox. Beyond building companies, she has been a transformative force in the Python open source community, growing Boston's Python user group to the world's largest, and teaching Python inside San Quentin State Prison. Pilot reached unicorn status in 2021 with a $1.2B valuation and over $222M raised from Sequoia, Index Ventures, and Bezos Expeditions.

- **Role:** CEO at Pilot.com
- **Organizations:** Pilot.com, Python Software Foundation, The Last Mile
- **From:** Cambridge, Massachusetts, United States
- **Nationality:** American
- **Education:** Bachelor's and Master's in Computer Science, Massachusetts Institute of Technology (MIT)
- **Known for:** Co-founded Pilot.com, the largest accounting firm for startups in the US, valued at $1.2B, Raised $222M+ from Sequoia Capital, Index Ventures, and Bezos Expeditions, Grew Boston Python user group from 700 to 4,000+ members, making it the world's largest

## Career timeline

- **2009-2011** — Engineering manager at Ksplice, building rebootless Linux kernel updates; company acquired by Oracle in 2011
- **2012** — Co-founded Zulip, a group messaging and collaboration platform
- **2012-2014** — Director on the Python Software Foundation board; grew Boston Python user group from 700 to 4,000+ members
- **2014** — Zulip acquired by Dropbox
- **2014-2017** — Director of Engineering and Chief of Staff to VP of Engineering at Dropbox
- **2017** — Co-founded Pilot.com with Waseem Daher and Jeff Arnold, serving as CTO
- **2021** — Pilot raised $100M Series C, achieving unicorn status at $1.2B valuation
- **2024** — Transitioned from CTO to CEO of Pilot.com

## Achievements

- Co-founded Pilot.com, the largest accounting firm for startups in the US, valued at $1.2B
- Raised $222M+ from Sequoia Capital, Index Ventures, and Bezos Expeditions
- Grew Boston Python user group from 700 to 4,000+ members, making it the world's largest
- Increased women's participation in Boston Python from 0-2% to 15%
- O'Reilly Open Source Award, 2013
- Frank Willison Award from the Python Software Foundation, 2015
- Red Hat Women in Open Source Community Award, 2016
- Senior technical advisor for 16 episodes of HBO's Silicon Valley
- Co-founded Zulip (acquired by Dropbox in 2014)
- Director of the Python Software Foundation (2012-2014)
- Keynote speaker at PyCon 2019

## Latest updates

- **2024-07** — Transitioned from CTO to CEO of Pilot.com
- **2024-01** — Pilot launched AI Accountant, a fully autonomous virtual worker for bookkeeping and financial reporting
- **2021-03** — Pilot raised $100M Series C at $1.2B valuation, achieving unicorn status

## Links

- Website: https://pilot.com
- LinkedIn: https://www.linkedin.com/in/jesstess
- Twitter/X: https://twitter.com/jessicamckellar
- GitHub: https://github.com/jesstess
- Facebook: https://facebook.com/PilotHQ/

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Profile page: https://yespress.io/jessica-mckellar
Published by YesPress — https://yespress.io
Last updated: 2026-05-26