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WAYLINE

AI voice for property managers

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
Jason Okra
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.
Eric Rowell
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.
Company Launches
Wayline: AI voice and text for property managers
See original launch post

TL;DR
Wayline is voice AI and text for property managers that automates all tasks traditionally handled by receptionists, leasing agents, and maintenance coordinators. Imagine staffing an always-on property assistant that can convert leads and resolve issues instantly, day or night. Instead of robo-menus or call centers, every call and text is answered instantly by AI that knows the property better than the onsite teams.

We bring a decade of property tech and real estate operations experience, having bootstrapped a management company to $1M ARR, run WeLive’s global operations, and oversaw WeWork’s $110M All-Access product. We’re also multi-time founders, having raised $25M+ across three YC-backed companies, and built platforms at LinkedIn and Workday. Together, we combine deep real estate expertise with repeat founder experience in AI and enterprise software.

https://www.youtube.com/watch?v=csrPXRzr6zU

The Problem

Property management is human-intensive, low-margin, and full of repetitive communication. Operators juggle endless leasing calls, maintenance triage, and support inquiries - all while managing constant staff turnover and fragmented tools like AppFolio, Yardi, and spreadsheets. The result: overworked teams, missed opportunities, and reactive service.

The Solution

Wayline is the new front desk for real estate. Property management is largely administrative work - phone calls, coordination, and repetitive workflows - and we automate all of it with AI and a property-specific knowledge base. We pull in data from hundreds of public and proprietary sources to resolve issues in real-time and automate follow-up workflows. For tenants and prospects, calling or texting the building is the interface. For operators, Wayline centralizes and scales what used to take teams of on-site managers and assistants.

Why Now

Real estate has resisted disruption for decades with fragmented platforms, duct-taped point solutions, and thin margins. However, AI changes the labor equation: for the first time, the administrative side of property management can be run largely by software. And unlike human teams, AI never sleeps or churns.

The Team

  • Jason Okra previously led WeWork’s $110M All-Access product, ran WeLive’s global operations, and bootstrapped a property management company to $1M ARR.
  • Eric Rowell is a 3x YC founder who has previously raised $23M+, architected the LinkedIn homepage, and was the Head of Data Visualization at Workday.

We’re building the AI operator for the 46M rental units in the US. Learn more at wayline.com

Jobs at WAYLINE
San Francisco, CA, US
$190K - $240K
1.00% - 3.00%
3+ years
San Francisco, CA, US
$190K - $240K
1.00% - 3.00%
3+ years
WAYLINE
Founded:2025
Batch:Summer 2025
Team Size:2
Status:
Active
Primary Partner:Gustaf Alstromer