Introduction
What happens to a startup pitch when every single submission in the pile says AI on it? Stacey Brown has a useful vantage point on that question, because his Innovation Challenge is one of the few places where carriers actually sit down and read what startups send them. Submissions for the 2026 challenge close on October 7, roughly sixty had come in when this conversation was recorded, and Stacey expects the usual rush at the end.
In this episode, Josh Hollander and Stacey work through how the challenge is judged, what separates a submission that scores well from one that does not, and why Stacey thinks reviewers this year will spend less time looking at the technology than at the problem the technology solves.
Guest Bio
Stacey Brown is the founder and president of InsurTech America. He spent more than twenty years as an insurance IT executive before noticing how much investor money was moving into startups built to disrupt the industry, and started reaching out to people around Hartford to talk about it. That became InsurTech Hartford, and by 2023 it had grown enough that he left the day job for it. InsurTech America now runs six regional communities spanning Hartford, New England, Atlanta, Chicago, Florida and the Carolinas, and its Innovation Challenge is in its third year, having drawn more than three hundred startups from over a dozen countries, with winners from Australia, Germany and Israel.
Key Topics
-AI has stopped being an answer - Everyone is expected to have it now, which means claiming it no longer distinguishes anyone, and Stacey's read is that reviewers will be looking at the problem being solved rather than the tech solving it.
-What the 2026 categories actually want - The Hartford is sponsoring the Future of Customer Protection Award for AI and emerging technologies applied to preventing and quantifying risk, and Travelers is sponsoring a prize for the best emerging product or service addressing technological, societal or economic change.
-A student track, limited to Connecticut - New this year, and constrained to Connecticut students because of how the state support is structured.
-A path to the Startup World Cup - The Innovation Challenge is now an official qualifier for the Pegasus Tech Ventures competition, where the grand prize is a one million dollar investment.
-How submissions are judged - Every submission is read by carriers, at least two reviewers each, scored, then narrowed to three finalists per category who present to a panel of judges.
Why submitting early matters - Reviewers start on early submissions before the deadline crush, so the same material gets better attention if it arrives sooner.
-The new mentor program - Six cycles of two weeks each, with at least one thirty-minute meeting per cycle, structured around product, customer, go-to-market and business strategy, and built to fix the thing that usually goes wrong with mentorship.
-Losing can still be worth it - Carriers read everything, so a submission that does not win can still catch someone's interest, and being named a finalist carries its own recognition.
Notable Quotes
"AI is not the differentiator anymore. You need more than AI."
"People aren't going to be looking at the tech as much as they're going to be looking at the problems that are being solved by the tech."
"It's amazing how many startups are out there that can't actually articulate who their target buyer is."
"If you don't get a strong mentor, you're not going to have a strong experience."
Resources
Guest:
InsurTech America: https://insurtechamerica.com/
Stacey Brown on LinkedIn: https://www.linkedin.com/in/staceybrown/
Host & Organization:
Joshua R. Hollander on LinkedIn: https://www.linkedin.com/in/joshuarhollander/
Horton International (USA): https://www.horton-usa.com/
Insurtech Leadership Podcast (LinkedIn Showcase): https://www.linkedin.com/showcase/insurtech-leadership-show
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