Wayline

Wayline builds an AI-based voice and text assistant for residential real estate operators. Its product, referred to as Operator, answers inbound phone calls and messages 24/7 on behalf of property managers, handling leasing inquiries, maintenance triage and general resident support. The system is described as combining AI with human staff in a collaborative model, working alongside the operator's existing phone systems and property management software rather than replacing them.

Functionally, the company groups the product into three roles: an AI receptionist that answers calls and texts, greets residents with lease context, handles FAQs, policy questions, package and visitor matters, and transfers to human staff with a briefing; an AI leasing agent that qualifies inbound leads, communicates availability and pricing, schedules tours and follows up automatically; and an AI maintenance coordinator that triages requests by severity, generates work orders, schedules vendors, tracks completion, closes tickets and sends status updates to residents. The company also cites weather-triggered maintenance alerts.

Wayline states its longer-term aim is a next-generation property management system — a human-AI collaborative agent able to oversee maintenance, support, leasing and communication for hundreds of units simultaneously. Its stated thesis is that automating property operations lowers cost and expands housing access and supply rather than delivering only marginal efficiency gains.

Founding story

Wayline was co-founded in 2025 by Jason Okra (CEO) and Eric Rowell (CTO). Okra previously led WeWork's $110M All-Access commercial business, ran WeLive's global coliving operations, headed software development at hospitality provider Jupe (YC S21), advised apartment-finder Kopa (W19), founded prop-tech startup Cribspot (YC W15) whose team joined ApartmentList in 2018, and bootstrapped Baker Street Properties, a boutique property management company, to $1M ARR. Rowell was previously founder and CEO of Second (YC W23), co-founder and CTO of Uiflow (YC W21), which was acquired by Workday, Head of Data Visualization at Workday, and a UI architect at LinkedIn and Yahoo, as well as author of the HTML5 Canvas Cookbook. The company describes its tools as shaped by firsthand operational need from that background.

Business model

Wayline sells software to property management companies and real estate operators, providing an AI front-desk service that answers inbound calls and text messages and executes leasing, maintenance and resident-support workflows. The product is positioned as a replacement for robo-menus, call centers and portions of on-site administrative staffing, and is delivered as an always-on service layered on top of the operator's existing phone and property management systems. A customer login portal at app.wayline.com indicates a hosted account-based product.

Sources describe a B2B software service sold to property managers and real estate operators; specific pricing or contract terms are not stated.

Traction

Public materials report that 94% of phone calls are handled automatically, a 99.2% after-hours call handling rate, a 48% increase in lead-to-showing conversion at Baker Street Properties, and 34% of maintenance calls resolved end to end without human input. The company's site displays a 4.8 out of 5.0 user rating and lists integrations and operators including Entrata, Airbnb, RingCentral, RealPage, Buildium, AppFolio and Yardi. Y Combinator lists the team size at five as of its profile.

Latest developments

Wayline completed the Y Combinator Summer 2025 batch and launched its AI voice and text product for property managers, publishing operational figures including 94% of calls handled automatically, 99.2% after-hours call handling, a 48% increase in lead-to-showing conversion at Baker Street Properties, and 34% of maintenance calls resolved end to end. Its Y Combinator profile lists the company as active with a team of five and an open Customer Success Manager role in San Francisco.