Wayline

AI voice for property managers

Y CombinatorSummer 2025ActiveReal Estate and Construction

What they do

Problem

Property managers miss leads and struggle to handle tenant and prospect calls/messages 24/7 while scaling support across portfolios.

Solution

An AI front desk voice and messaging assistant for real estate that answers and resolves requests around the clock and integrates with existing phone and property management systems.

Who it's for

Property management companies and real estate operators managing leasing and tenant support.

Founders

Jason Okra

Founder

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.

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Eric Rowell

Founder

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.

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