# Jason Chicola

> Jason Chicola is the founder and CEO of Rev, the Austin-based speech-to-text company that pairs 50,000 freelance transcriptionists with best-in-class AI to turn spoken words into searchable text. An MIT-trained engineer who became the third employee at oDesk (now Upwork), he built Rev on a simple bet: people will pay for curated quality, and people everywhere want to work from home. Today Rev serves over 100,000 clients including 60% of the Fortune 500, and Chicola is steering the company toward AI tools for the legal system, where accuracy is not optional.

- **Role:** Founder & CEO at Rev
- **Organizations:** Rev, Temi, Upwork (formerly oDesk), H.I.G. Capital, Globespan Capital Partners, McKinsey & Company
- **From:** Miami, Florida, United States
- **Nationality:** American
- **Education:** High school, Miami Palmetto Senior High School, B.S. in Electrical Engineering, Computer Science, and Economics, Massachusetts Institute of Technology (MIT)
- **Known for:** Founded and scaled Rev to over 100,000 clients, including roughly 60% of the Fortune 500, Built a global network of about 50,000 freelance transcriptionists and captioners, Was the third employee (and first non-engineer) at oDesk, now the publicly traded Upwork

## Career timeline

- **1996** — Arrives at MIT, gravitates toward computer science; joins Kappa Sigma fraternity
- **2000s** — Works at McKinsey (consulting), Globespan Capital Partners (venture capital), and H.I.G. Capital (private equity)
- **2004** — Meets the founder of oDesk and becomes its third employee - and first non-engineer - later serving as Director of Marketing & Sales
- **2010** — Founds Rev alongside MIT fraternity brothers to create quality-guaranteed work-from-home jobs
- **2018** — Launches Temi, an automated (AI-only) transcription service
- **2025** — Rev acquires SmartDepo to power AI deposition summaries; named first AI partner of the State Bar of Texas
- **2025** — Publishes CEO note repositioning Rev as an AI investigative platform for the legal system

## Achievements

- Founded and scaled Rev to over 100,000 clients, including roughly 60% of the Fortune 500
- Built a global network of about 50,000 freelance transcriptionists and captioners
- Was the third employee (and first non-engineer) at oDesk, now the publicly traded Upwork
- Earned an 82/100 CEO approval rating from employees, placing him in the top 10% of similarly sized companies (Comparably)
- Led Rev's acquisition of SmartDepo and its selection as the first AI partner of the State Bar of Texas
- Earned three undergraduate degrees at MIT in EECS and Economics

## Latest updates

- **2025-03** — Rev acquired SmartDepo to build next-generation AI for legal testimony analysis and deposition summaries.
- **2025-10** — Rev named the first-ever AI partner of the State Bar of Texas.
- **2025-11** — Chicola published a CEO note framing Rev's future as an AI investigative platform for the legal system.
- **2026-03** — Featured in Law.com discussing how Rev addresses the legal 'discovery bottleneck and burnout crisis.'

## Links

- Website: https://www.rev.com
- LinkedIn: https://www.linkedin.com/in/jasonchicola/
- Twitter/X: https://twitter.com/rev
- Facebook: https://www.facebook.com/revdotcom

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Profile page: https://yespress.io/jason-chicola
Published by YesPress — https://yespress.io
Last updated: 2026-07-01