Wayline
Summer 2025AI voice for property managers
About Company
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.
Active Founders
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.
Co-founder & CTO of Wayline (YC S25). I was previously the founder & CEO of Second (YC W23) where I raised $1.9M to build enterprise codebase maintenance tools. Before that, I was the co-founder and CTO of Uiflow (YC W21) where I raised $21M, built a no-code platform for enterprises, and was acquired by Workday. Before that, I was the Head of Data Visualization at Workday, UI architect at LinkedIn and Yahoo, author of HTML5 Canvas Cookbook, and created several popular open source libraries.