My dad was a roofing contractor, and growing up, I watched him fight through thousands of insurance claims.
Eventually, his company stopped doing insurance work altogether. It wasn’t because there wasn’t demand. It was because getting paid became too much of a fight. The back-and-forth, documentation requirements, revisions, delays, and constant negotiation reached a point where they decided the work simply wasn’t worth the headache.
Years later, after leaving college during COVID and finding my own way into restoration, I started seeing the same problem firsthand.
And after talking with hundreds of restoration business owners, I’ve realized my dad’s experience wasn’t unusual.
Some contractors are still doing a tremendous amount of insurance work, but many feel like they have to fight tooth and nail to get paid for work they’ve already completed. Others have intentionally moved toward self-pay work or abandoned certain types of insurance jobs altogether.
That is one reason I’m so optimistic about AI.
There is obviously a lot of conversation about AI in restoration right now. Much of it focuses on how quickly we can write an estimate, generate a report, or automate another individual task.
Those things are useful. But I think the bigger opportunity is not simply doing the same work faster. It is questioning why we are doing so much of that work in the first place.
My generation is entering restoration without the same attachment to how the work has always been done. That creates an opportunity, but also a risk. We are probably more willing to question a workflow simply because it feels inefficient. But if we use AI only to automate the workflows we inherited, we may miss the chance to rethink why those workflows exist at all.
What if AI could make insurance work less painful?
What if better technology could help contractors document a loss correctly from the beginning, identify missing information before it becomes a problem, build a defensible estimate, organize the evidence supporting it, and respond when something gets questioned?
Maybe a contractor who previously decided insurance work wasn’t worth the headache could reconsider.
Maybe an owner could spend less time fighting over claims and more time building their company and developing their people. Or even spend more time with their kids…
That is the kind of AI adoption I want to see.
I’ve always been optimistic about what AI will bring. I believe it will create opportunities for people who previously didn’t have them. I also believe the next decade will be difficult for businesses that choose not to adapt.
But adopting AI shouldn’t mean automating things simply because we can.
There is a big difference between improving a process and simply accelerating it. If a frustrating workflow has ten steps, using AI to complete all ten faster may be progress. But the better question might be whether all ten steps should exist.
We should be looking at the work that frustrates us, slows us down, and keeps talented people buried behind a computer, and asking whether technology can take more of that burden.
One thing I’ve learned from great restoration contractors is that most of them care deeply about what they do. They aren’t just drying buildings or rebuilding houses. They are walking into someone’s life after a fire, flood, hurricane, or other disaster and helping put things back together during one of that person’s worst moments.
If my generation can bring anything useful to this conversation, I hope it is a willingness to keep asking why. Why does this take so long? Why are we entering the same information multiple times? Why does a contractor have to fight so hard to support work they’ve already performed? And if we were designing the process today, would we build it the same way?
AI gives us the chance to do more than speed up the work we inherited. It gives us a chance to reconsider the work itself. I think that is where the real opportunity is.
Dalton Gregory
Dalton Gregory is the co-founder and CEO of Plentitude, a technology company building the next generation of tools for the restoration industry, starting with estimating and claims intelligence. With a background in restoration, AI, and helping contractors adopt new technology, Dalton is focused on rethinking how restoration companies use technology to reduce friction and scale their operations.
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