Barriers and Breakthroughs: What 61 Insurance Leaders Told Us About Why Transformation Really Stalls

Insurance Business has spent years in conversation with the people actually building transformation inside this industry, carriers, brokers, MGAs, the leaders making the buying decisions. So when we set out to understand why so many technology programs stall while others pull ahead, we didn’t ask vendors. We asked their buyers.

61 senior leaders, most of them C-suite, told us directly what separates the tools that stick from the tools that get shelved. If you sell into this industry, it’s worth hearing in their own words.

A few things came up again and again. Access to good technology stopped being the differentiator a while ago; every serious buyer can find a capable model or a credible vendor now. What they’re actually screening for is whether you’ll be there in three years, whether you understand their process well enough to build to it instead of forcing them into yours, and whether you can prove your accuracy claims rather than just make them. One leader told us plainly: they don’t fall in love quickly.

We also heard, unprompted, exactly how the best vendor relationships in this industry actually got built. Not through a polished pitch deck. Through small pilots, real colleagues vouching for the product, and a willingness to be evaluated against ground truth instead of a demo.

None of this is guesswork. It’s drawn from named conversations with leaders at Travelers, Swiss Re, AXA XL, Sedgwick, Amwins, Texas Mutual and dozens more, organized into six findings on how insurance actually buys, adopts, and stays with technology.

If you’re building for this market, this is what your buyers are telling each other when you’re not in the room.