3 years in hibernation, Milestones emerges with $10M in funding – Inman

Milestones’ client retention model is not entirely new, but the company hopes its new funding and team of backers can deliver a unique message to the market.
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After three years of development, testing and product refinement — a growth phase the technology industry calls “stealth mode” — a company called Milestones has emerged from its skunkworks hovel flush with $10.3 million in Series A funding.
The company is pitched as an “all-in-one homeowner portal, making it easier for consumers to buy, move, sell and manage their home,” in an announcement on the launch sent to Inman.
Updater, itself enriched after pocketing $60 million in financing at the end of 2021, was the primary source of funds for Milestones.
Other groups participated in the fundraising namely Second Century Ventures (the strategic investment arm of the National Association of Realtors), Peerage Capital, McLaughlin Ventures, WAV Group Ventures, T3 Partners and Sellers Shield.
Naturally, the company is raring to meet the market.
Milestone’s client retention model is not entirely new, but the company hopes its new funding and team of backers can deliver a unique message to the market.
“The average home has more than 150 systems that need to be maintained and consumers need help keeping it all organized,” said Dustin Gray, Milestones founder and CEO, in the press release. “Gutters need to be cleared, water filters replaced, concrete sealed, dryer vents cleaned and so on. Milestones has checklists for all of it, complete with DIY videos, or access to professionals who will do it for you.”
Claiming in the announcement to be, “the first technology firm to deliver a home ownership portal similar to consumer offerings for managing healthcare, personal finance, and education,” a number of companies crowd this category, including options from significant proptech stalwarts like Inside Real Estate, MoveEasy and MooveGuru among several other players.
The product’s features include home-value monitoring, home search and intrinsic transaction management, which helps Milestones stand out slightly from the crowd, Inside Real Estate’s CORE Home notwithstanding.
While home management apps intend to encourage homeowners to remain in close touch with the upkeep and thus the value and market positioning of their homes, the value to real estate agents is often difficult to sell. Home search tools and transaction tools can help remedy that, however, as they offer a direct line of consistent contact with agents to help bridge the years between sales.
“Milestones is available to consumers at no cost, in partnership with real estate professionals in brokerage, mortgage, title, and insurance,” the release stated.
In a company-produced video introduction, Gray hits all the right notes in explaining the intent of his company, pointing out that a transaction-oriented mindset can hamper an agent’s long-term success.
“[Instead], they should be a fiduciary advisor for all things real estate no matter where someone was in the process of buying, moving, owning or selling.”
Maintaining close contact after closing is a major challenge for the industry. Years of home ownership create new relationships for clients and unseen marketing challenges for agents. Friends become agents, agents move brokerages and alliances shift.
The National Association of Realtors’ Profile of Home Buyers and Sellers found that 75 percent of buyers would use their agents again or recommend their agents to others, yet only a little over half, 53 percent, actually do.
Milestones hopes to tighten that margin and David Greenberg, founder and CEO of Updater, is confident the company’s approach and Updater’s influence will pinch the gap.
“Convenience and simplicity are core to the Updater mission,” Greenberg said in the release. “With
our shared vision for simplifying the complex home ownership processes, Updater’s investment in Milestones is a natural fit.”
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