2023 HW Vanguard: Dustin Gray

Dustin Gray

Dustin Gray, CEO of Milestones, started a career in real estate technology in 1996. He apprenticed at a local commercial real estate brokerage as a sales agent for five years during college, then went on to earn his CCIM designation. He joined the CCIM Institute and concurrently co-founded a commercial MLS, Catylist. Catylist scaled into 80 metros and was later acquired by Moody’s. After business school, Gray joined Deloitte’s global real estate group and worked extensively with real estate data to drive large-scale real estate CAPEX projects. From there, he led the consumer products division of RealPage and served as the head of operations at Realtor.com following its acquisition of Opcity. This background led to the founding of Milestones, a comprehensive homeownership platform to modernize the real estate experience in a way that makes it more profitable for professionals and more seamless for consumers. Gray’s contribution to the organization is to help articulate a vision, attract talent and make sure that Milestones is capitalized for success. Gray’s vision is for companies to ruthlessly focus on the homeowner or rest assured that someone else will. Gray took on the challenge to build a homeownership portal for consumers that is delivered through real estate professionals, mortgage professionals and title professionals. The company was deployed by 250,000 real estate professionals within the first 160 days of launch.

What’s the best advice you’ve ever received?

Time is not our friend. Focus on what you can get done by five o’clock today, because you never know what tomorrow will bring.


Dustin Gray



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3d rendering of a row of luxury townhouses along a street

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