GWRE
GUIDEWIRE SOFTWARE, INC.
stock NYSE

Just did some DD on Guidewire Software (GWRE) and boy, if only one SaaS company exists that is AI proof, it could be them. They are the P&C insurance industry's core operating system. Insurance companies run policy, billing, and claims operations through Guidewire's cloud platform. They started their transition from licensing to subscription in 2017 but didn't really accelerate it until 2019. Gross margins on the SaaS segment has gone from 38% in 2021 to 68% in 2025 (their fiscal year ends July 31). ARR is accelerating, RPO has been >33% every year they've reported it (since 2019), including a 55% jump in 2025 (attributed to a very larger insurer that signed a 10-year contract).
Switching costs are measured in years and hundreds of millions of dollars and the idea that an insurance company is going to vibe code a new solution that maintains privacy and security and not jeopardize seamless operations while re-train the remaining staff, it's just crazy in my opinion. And yet, they are in a 53% drawdown, caught up in the SaaSacre.

Just did some DD on Guidewire Software (GWRE) and boy, if only one SaaS company exists that is AI proof, it could be them. They are the P&C insurance industry's core operating system. Insurance companies run policy, billing, and claims operations through Guidewire's cloud platform. They started their transition from licensing to subscription in 2017 but didn't really accelerate it until 2019. Gross margins on the SaaS segment has gone from 38% in 2021 to 68% in 2025 (their fiscal year ends July 31). ARR is accelerating, RPO has been >33% every year they've reported it (since 2019), including a 55% jump in 2025 (attributed to a very larger insurer that signed a 10-year contract).
Switching costs are measured in years and hundreds of millions of dollars and the idea that an insurance company is going to vibe code a new solution that maintains privacy and security and not jeopardize seamless operations while re-train the remaining staff, it's just crazy in my opinion. And yet, they are in a 53% drawdown, caught up in the SaaSacre.