3x founder

Jason Okra

3x PropTech Founder | Ex WeLive/WeWork | AI x Real Estate (YC S25)

Founder

Wayline· Summer 2025 🇺🇸 San Francisco, California, United States

in LinkedIn 𝕏 @heyokra

2025Founder· Wayline

Founder · since 2013

Company

Wayline

Role

CEO & Founder

current

Stage

—

no public source

Raised

—

no public source

Based

—

Founder / co-founder — the company's markEmployee / research role

Source: LinkedIn work history

Profile coverage5 of 7 · missing posts, contact

Wayline

AI voice for property managers

Summer 2025

Experience

Career

Wayline
Founder
CEO & Founder · 2025 – Present
2025
Baker Street Management
Founder
CEO & Founder · Ann Arbor, Michigan, United States · 2018 – Present
2018
Webflow
Product · 2023 – 2025
2023
Itana
Advisor · 2022 – 2024
2022
JUPE
Head of Product · San Francisco Bay Area · 2022 – 2023
2022
WeWork
Director of Product · New York, New York, United States · 2020 – 2022
2020
WeWork
Welive, Product Owner · 2019 – 2020
2019
Apartment List
Soft Landing · 2018
2018
Cribspot (YC W15)
Founder
CEO & Founder · Ann Arbor, MI · 2013 – 2018
2013
SeatGeek
Marketing Intern · New York City Metropolitan Area · 2012 – 2013
2012

Bio

CEO and Co-founder of Wayline. Jason formerly led WeWork’s commercial $110M All-Access business, ran the WeLive coliving product, headed software development at the hospitality provider Jupe (YC S21, Initialized-backed), and advised apartment-finder Kopa (W19). Previous to that, he founded and bootstrapped Baker Street, a boutique property management company to $1M ARR. In addition, Jason founded the multi-family prop-tech startup Cribspot (YC W15), with the team joining Apartmentlist in 2018.