Homeowner.ai

We are Homeowner.ai

You serve homeowners, we serve you.

We partner with industry to make homeownership easier, at every step of the journey.

Our mission is to enable long-term, profitable homeowner relationships that benefit both homeowners and the industry as a whole.
We have pioneered homeowner portals, private hubs designed to help consumers build wealth and efficiently manage their homes, all while working hand in hand with trusted advisors.
Through our innovative solutions, our customers benefit from increased lead conversion, client satisfaction, loyalty, and cross-sale opportunities.
Homeownership Timeline

Our Story

Made with 🧡 in Austin, TX

Getting a home is exciting, however, owning a home is challenging.

Homeowners struggle to manage maintenance, repairs, improvements, and finance. For many, the journey is a series of unpleasant surprises and unplanned expenses, which gets stressful quickly. Unfortunately, trustworthy and reliable help is hard to find.

Meanwhile, industry professionals face their own challenges including high customer acquisition costs, low loyalty, and limited information about what’s under each roof.

Inspired by the healthcare sector’s personalized approach to an expensive industry with complex issues, we founded Milestones in 2019 to bridge the gap between homeowners and industry professionals.

"If you visit a doctor, you get a patient portal, so why isn't there something similar for your home?"

Initially only serving clients in real estate, mortgage, and title companies, our platform has since expanded to include insurance, home warranty, home services, mortgage servicers, and homebuilders. 

In 2024, we renamed our platform Homeowner.ai, a Milestones company, reflecting our commitment to modernizing and enhancing the homeownership journey in collaboration with consumers and industry.

Our Leadership Team

Dustin Gray

Founder, Chief Executive Officer

Mike Malinowski

Chief Operating Officer

Mike Silkett

Chief Product Officer

Mishu Vlad

Founder, Chief Technology Officer

Celeste Filiatrault

Founder, Chief Experience Officer

Shannon Baldwin

Chief Marketing Officer

Bill Sperry

Head of Real Estate

Robert Houser

Head of Mortgage

Our Board of Directors

Dustin Gray

Homeowner.ai

Mark McLaughlin

McLaughlin Ventures

Brian Maughan

Fidelity National Financial

Scott Gordon

Open Mortgage

Tony Meola

West Coast Advisory, LLC

Our Strategic Advisors

Victor Lund

Jeremy Foster

David Garland

Jack Miller

David Lykken

York Baur

Sue Woodard

Tristan Ahumada

Simon Chen

Jim Black

Smokey Garrett