About
Jason led WeWork's All-Access commercial business and WeLive coliving product, served as head of software development at hospitality provider Jupe, and previously founded and bootstrapped Baker Street property management company and Cribspot, a multifamily property-technology startup that was acquired by ApartmentList in 2018.
OKRA π± @heyokra
For all the venture funding ($1.85B), @Rippling has some terrible UX. So much mental fatigue navigating their flows, hunting for the right screen to edit something as critical as an auto-pay setting. The future is clearly agents retrieving & updating info on-demand with minimal
May 6, 2026 Β· β₯ 4
OKRA π± @heyokra
dear @webflow community, what CMS-related problems and features do you wish we could solve for in 2024?
Jan 1, 2024 Β· β₯ 71 Β· β 9
Founder at CribspotYC W15
Intro paths
Jason went through Y Combinator (Winter 2015) β any YC alum in your network can reach them through the YC community.
In turn, Jason can intro founders to Cribspot's investors below.
Cribspot's investors Β· 1
Co-founders at Cribspot
Founder at WaylineYC S25
Intro paths
Jason went through Y Combinator (Summer 2025) β any YC alum in your network can reach them through the YC community.
Their group partner at YC was Gustaf Alstromer β the partner who ran Wayline's batch and knows the company first-hand. YC profile β
In turn, Jason can intro founders to Wayline's investors below.
Wayline's investors Β· 3
Co-founders at Wayline
