# Jason Okra

> Jason Okra is the CEO and co-founder of Wayline, a San Francisco company building AI voice and text tools for property managers. His career began with Cribspot, a University of Michigan housing search project that entered Y Combinator in 2015 and expanded into property management. He later founded Baker Street, worked on WeLive and WeWork’s All-Access product, and led product work at Jupe and Webflow before returning to Y Combinator with Wayline in Summer 2025.

- **Role:** CEO & Co-founder at Wayline
- **Organizations:** Wayline, Cribspot, Baker Street Properties, WeLive, WeWork, Jupe, Webflow, Kopa, Y Combinator
- **Education:** Bachelor of Business Administration, University of Michigan - Stephen M. Ross School of Business, Y Combinator
- **Known for:** Co-founded Cribspot, a YC W15 company that expanded from housing search to property management., Baker Street passed $1 million in annual recurring revenue, according to his founder biography., Led technology rollout for WeWork All-Access and On-Demand; he reports approximately $110 million in annual revenue by 2022.

## Career timeline

- **2012** — Housing search project a2cribs.com launches while the founders are University of Michigan students.
- **2013** — Project relaunches as Cribspot; Okrasinski graduates from Michigan Ross.
- **2014** — Cribspot participates in Bizdom and places second in the Accelerate Michigan Innovation Competition.
- **2015** — Cribspot joins Y Combinator Winter 2015 and begins managing properties.
- **2018** — Cribspot team joins Apartment List; Baker Street Properties is founded.
- **2019** — Joins WeLive at WeWork, working on flexible housing.
- **2022** — WeWork All-Access and On-Demand product lines reach roughly $110 million in annual revenue, according to Okra; later product work includes Jupe and Webflow.
- **2025** — Co-founds Wayline with Eric Rowell and returns to Y Combinator in its Summer batch.

## Achievements

- Co-founded Cribspot, a YC W15 company that expanded from housing search to property management.
- Baker Street passed $1 million in annual recurring revenue, according to his founder biography.
- Led technology rollout for WeWork All-Access and On-Demand; he reports approximately $110 million in annual revenue by 2022.
- Co-founded Wayline, accepted into YC Summer 2025.

## Latest updates

- **2025-08** — Announces his return to Y Combinator with Wayline and Eric Rowell; reports thousands of units under management after six weeks.
- **2026-10** — At the research date, Wayline markets an AI and human operations service covering leasing, maintenance, billing and communication; Baker Street lists Okra on its advisory team.

## Links

- Website: https://www.wayline.com/
- LinkedIn: https://www.linkedin.com/in/okra/
- Twitter/X: https://x.com/heyokra

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Profile page: https://yespress.io/jason-okra
Published by YesPress — https://yespress.io
Last updated: 2026-10-12