Join Date
March 2026
Gender
Not Specified
Age
Not Specified
About Jason Okra
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.
Companies & Work
Wayline
Wayline is an AI front desk assistant purpose-built for real estate to answer calls and messages 24/7. It’s like an always-on property manager that can convert leads and resolve issues better than any human, day or night. Our AI can be setup in as little as 24 hours and works seamlessly with existing phone/management software. Uniquely, our AI knowledge base is domain-specific to learn and handle the most complex real estate workflows. For property operators, Wayline instantly replaces robo-menus and call centers, while centralizing and scaling back-office teams.
