One of the hardest parts of being a homeowner is knowing whom to call when something goes wrong with your house—a process that starts with figuring out what’s actually wrong in the first place.  “What if you wake up, you’ve got a wet spot on the ceiling, and you’re like, Oh crap, I’ve got a problem, but I don’t actually know what it is or who to hire ?” says Marco Zappacosta, cofounder and CEO of the home-services marketplace Thumbtack. The 18-year-old platform has made a robust business of helping homeowners navigate the sometimes bewildering process of home improvements and repairs by connecting them with all sorts of service pros—handymen, roofers, electricians, plumbers, and more—faster and more efficiently than traditional methods. Last year, Thumbtack took in nearly $500 million in revenue, according to Zappacosta, up 24% year over year. The company, he says, is “meaningfully profitable.” (Thumbtack makes money by charging professionals a fee for each introduction to a customer.) More than 4.5 million users turned to Thumbtack to help with some 8 million projects over the past 12 months alone, up 15% over the past year. Even so, finding the right person for the right job remains daunting. There are, after all, more than 300,000 pros on Thumbtack, each with a unique set of skills.  Thumbtack has been using AI for years to refine how users search for pros on its platform. But LLMs have unleashed new possibilities for matchmaking, and the company is now launching an entirely redesigned app experience: Instead of searching for service pros, users are guided to them via an AI -driven interface that starts with homeowners simply describing what they’re seeing.  The new UX asks users to describe their problem in plain language, upload photos, and answer a few tailored questions. Thumbtack’s AI then interprets the problem and serves up a handful of pros whose expertise matches the issue. “We can now meet you where you are,” Zappacosta says. “You don’t have to know or be sure of anything.”   An AI guide to home repairs Thumbtack’s new experience builds on a feature the company introduced last year that incorporated natural language processing into search . But instead of acting as a separate chatbot or a stand-alone search feature, AI is now “baked into everything we do,” says Zappacosta, helping users throughout the entire life cycle of working with a pro. For users, the AI-guided UX not only lowers the hurdles to beginning a new project, it also reduces the uncertainty that surrounds the hiring process. Thumbtack now narrows the list of results users see to a curated few pros and explains why each is a good fit. “You can look at the most hired in your neighborhood, the person whose price is most competitive, or maybe the person who has the soonest availability,” Zappacosta explains. “And with that, you make a confident hire.” [Photo: Thumbtack] The new product also eliminates barriers for professionals on the platform. Instead of asking them to fill out rigid questionnaires and checklists to supply Thumbtack with the right metadata to power searches, pros can use natural language to detail their expertise and set nuanced parameters for their work. For example, a pro can tell the AI, “I don’t travel more than 50 miles if it’s less than a $1,000 job, but if it’s over $1,000, game on,” Zappacosta says. The company is preparing to roll out a new communication layer that provides homeowners with Thumbtack phone numbers to keep their information private. Because these conversations happen through Thumbtack, the platform can transcribe them, generate AI summaries, set reminders, and help customers compare quotes side by side. Before this feature, Zappacosta says, Thumbtack had visibility into just the 30% to 40% of communications that happened directly inside the app’s chat feature. [Photo: Thumbtack] These conversations will also provide Thumbtack with another rich vein of unstructured data to refine its AI matchmaking, such as “details around who likes which jobs, what jobs they’re good at, pricing estimates, and how long things are going to take,” Zappacosta explains. “All of that is very context-, neighborhood-, and pro-specific”—and traditionally has been very hard for the platform to track. Thumbtack’s AI can add up to a lot of time saved for contractors, says Jack Marquardt, owner of Electric Avenue in Portland, Oregon, who has been on the app since 2017 and serves on its advisory board. He cites a recent example of a homeowner who wanted a garage door installed and mistakenly reached out to an electrician. Marquardt had to explain that while he could put in an outlet and get power to the door, he couldn’t install the door itself and that other companies specialize in such jobs. Thumbtack’s new tools should be able to weed out these dead-end leads while speeding up communications around pricing and other parameters. “We’re just all on the same page a lot faster,” Marquardt says. Professionalizing the pros Zappacosta hopes the new experience of Thumbtack incentivizes homeowners to be proactive about taking care of their houses, rather than just responding in times of crisis and need. He sees home maintenance, in particular, as an area for growth.  [Photo: Thumbtack] But perhaps the company’s biggest opportunity lies in helping its largely analog service providers further professionalize by becoming, as Zappacosta says, their “business sidekick.” The vast majority of Thumbtack’s pros, he notes, don’t really use any back-office software, beyond QuickBooks. “They don’t otherwise leverage software to delight their customers, to be super responsive, to provide digital invoicing and payments,” he says. “We’ve earned the right to help them do a whole lot more than we do with them today.”  [Photo: Thumbtack] Thumbtack isn’t announcing any back-office software just yet, but its timing would be good. Interest in skilled trades is growing amid concerns about AI’s impact on office jobs. Thumbtack has doubled the number of pros on its platform over the past five years, and Zappacosta notes that 40% of those who have joined since 2024 are younger than 35.   “The arc is often they become an apprentice, they become a technician, and then they’re like, Wait, I can go get my own jobs. I can build my own firm,” he says. “And they turn to Thumbtack to go do that.”  Marquardt, for his part, is happy to have AI assist him without fearing that it’ll replace him. “People can use AI to help educate themselves and maybe diagnose their own [home repair] issues,” he says. “But they’re still going to need skilled electricians to come and actually execute everything right.”