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One in Three Prospects Never Get a Follow-Up: Inside Grace Hill Data │ Jen Tindle, VP of Partnerships & Strategic Initiatives at Grace Hill

Summary

Jen Tindle is VP of Partnerships and Strategic Initiatives at Grace Hill, the multifamily training, compliance, and performance measurement company. Before Grace Hill, she led data and analytics at private equity firm Pennybacker Capital, then co-founded CREx, a commercial real estate technology company she ran as CEO. Outside of her day job, she writes a personal Substack on AI in commercial real estate and co-created Build Order, a podcast and essay series about how systems shape cities. She sits down with host Jacob Kosior to talk about what Grace Hill's data is actually showing across thousands of properties, including why one in three prospects never gets contacted after their tour, the fastest proptech consolidation she's seen in her career, and why AI adoption is often driven from the wrong seat of the org.

Despite all of the AI chatbots that are out there today to communicate with residents, our Grace Hill Mystery shopping data actually shows that one third of prospects are never contacted after the tour.

In This Episode

Takeaways

  • One in three prospects never gets contacted after a tour. Grace Hill's mystery shopping data shows that even with AI chatbots and automated communication tools widely available, a third of prospects still aren't being followed up with at all. Jen's view is that the fix isn't one thing. Leasing teams need more training, clearer policies, and AI working together to stop dropping the most basic step in the funnel.
  • The question operators are asking has completely flipped. Jen has been preaching for five years that consolidation needed to happen in proptech. Now it's happening faster than she's ever seen, and the driving force is AI. The panel question used to be "how do I get my team to use the products we're buying?" Today it's "how do I roll out AI safely and securely?" That flip is changing how every proptech company is thinking about M&A.
  • The number one priority for operators in 2026 is embedding AI into actual workflows. Giving everyone access to an LLM and dropping it on a knowledge base is impactful but it's not the win. Jen sees small real estate firms gaining a real margin advantage by embedding AI directly into how work gets done, automating processes and removing human error. The tools will keep leapfrogging each other. It doesn't matter which one you use. It matters whether you actually put it to work.‍
  • AI adoption has to be driven from the top, but it usually isn't. Jen's view is that executives should be the ones pioneering AI use, because if leadership isn't using it the rest of the organization won't either. The mistake is treating AI like a calculator and expecting consistent outputs every time. It's more like a junior analyst that reasons through problems and still needs a human in the loop on certain types of work. The operators who get that distinction move faster than the ones who don't.