Real estate

Wayline

Website
Founded 2025Origin source ↗Checked 2026-09-15

Overview

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.

Company description As recorded 2026-11-08
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Founders & team

Previously Level0, Wayline, WAYLINE

Company history As recorded 2026-11-08

Jason Okra

Founder/CEO

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.

LinkedIn X
Founder profile As recorded 2026-09-15

Eric Rowell

Founder/CTO

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.

LinkedIn X
Founder profile As recorded 2026-09-15
5team members reported
Source-reported As recorded 2026-09-15

Founded 2025 · Source

News & product activity

Sources & observations

Y Combinator

Profile depthverified profile
Website observationwebsite reachable
Last website check2026-11-11
Location · source statedSan Francisco, CA, USA
Pricing evidenceNo pricing page confirmed
Maturity: Not assessed · 3 of 6 areas documented

Source-based assessment · automated evidence rules

The retained text does not establish product availability or customer use.

Maturity is an evidence-based assessment, not a success rating. It may understate the current stage where evidence is limited. Coverage records documented areas, not a complete or independently audited company history.

Stage definitions
independent websitesource corroborationreachable websitedescriptive evidenceclassified market and modelsourced peoplesourced founding year
startup.observe Directory coverage · Sources & method