(Guidewire CEO Mike Rosenbaum on stage at Connections 2025. Source: Guidewire.)

Mike Rosenbaum opened his keynote at Guidewire Connections 2025 at The Fontainebleau in Las Vegas with characteristically self-deprecating humor. Gesturing toward the vast new theater, he quipped that the company had signed the event contract before the hotel was even built—and had worked with the designers “to make it as complicated as possible to get from breakfast to the session hall” so attendees would experience something akin to implementing PolicyCenter. “But it all worked out great,” he said.

He described the occasion as both his “favorite” and “most stressful” day of the year. “Now we have four levels of balconies to be stressed about,” he added, pausing for laughter before turning sincere. “Thank you for being here. And thank you for the opportunity to do work that matters, on behalf of an industry that matters.”

A Mission of Trust and Agility

Rosenbaum said Guidewire’s (San Mateo, Calif.) mission has remained unchanged for 25 years and would continue unchanged for 25 more—to create a platform insurers can trust, providing the agility to innovate, expand, and operate efficiently. The company’s impact, he noted, now spans more than 500 customers across 43 countries, with 150 cloud implementations running in production and 2,400 cloud environments in total.

He credited that progress to the community that surrounds Guidewire: 200 technology partners, 500 marketplace apps, 41 consulting partners, and 28,000 certified consultants. “We shouldn’t be bashful,” he told the audience. “Together we’ve built the world’s leading platform for insurance.” He turned to a slide crowded with customer logos and asked attendees to find their own. “Thank you very much for permission to use your logo,” he said.

From the Filing Cabinet to Generative AI

After celebrating the company’s global reach, Rosenbaum turned to the next phase of transformation: generative AI. He called the technology “a miracle,” marveling that a computer could “trick us into thinking it thinks.” The technology, he admitted, had already helped him write his speech.

Tracing the industry’s evolution, he asked the audience to picture a filing cabinet in an insurer’s basement—where policy numbers were once retrieved by turning a mechanical crank—and then to picture a fully modernized Guidewire implementation. The leap from one to the other, he said, was profound, and the leap ahead with large language models would be just as great.

He described a sequence of change already taking shape. Developer productivity is increasing as AI assists in writing and deploying code. Underwriting—long considered an art form rather than a process—is beginning to open to automation, as large language models can now synthesize vast amounts of data to support judgment-based decision-making. Claims, he said, will evolve more gradually, given the higher stakes and need for prudence, but even there, AI will augment human capability. And, ultimately, customer experiences will transform as conversational systems enable people to interact naturally with intelligent agents.

“I can’t tell you exactly how long this will take,” Rosenbaum said. “But if anyone tells you they know, you shouldn’t believe them. This will take hard work, care, and study—and we’re committed to making it happen.”

A Platform Strategy for the AI Era

Rosenbaum framed Guidewire’s approach to this new phase around three enduring principles: a trusted and open core system, insurance-specific context for AI applications, and a collaborative ecosystem that includes partners and customers. “These systems are useless without context,” he explained. “They need the data that lives in Guidewire. They need to understand workflows, policies, claims. That’s where we come in.”

He stressed that Guidewire’s AI evolution will not be proprietary but open and extensible. “We’re not going to lock up Guidewire and sell you back the key,” he said. “We got here because of the ecosystem, and that’s how we’ll move forward.”

Key Developments Defining 2025

Rosenbaum then detailed four major developments shaping Guidewire’s 2025 roadmap.

PricingCenter reimagines the rating process by uniting pricing and actuarial modeling within a single environment. By integrating the new application with core data and the Advanced Product Designer, Guidewire aims to eliminate bottlenecks and enable faster pricing innovation.

UnderwritingCenter introduces a core system optimized for underwriting, built around a submission workflow designed for the era of generative AI. The platform enables underwriters to ingest, evaluate, and prioritize submissions with efficiency, while integrating seamlessly with PolicyCenter and other core systems.

Generative AI services will be incorporated directly into the Guidewire Cloud Platform, giving developers access to tools for building intelligent workflows. Customers on the latest cloud release will be able to deploy these AI features quickly and safely across their organizations.

The acquisition of ProNavigator, announced the night before Rosenbaum’s speech, will add new capabilities for knowledge automation. The Toronto-based company has developed technology that pairs large language models with contextual data to make every user “as good as your best employee,” Rosenbaum said. “Three weeks, and you’re in production with a system that turns every single person into an expert.”

He closed by acknowledging the uncertainty that comes with transformation but expressed confidence in the foundation that has carried Guidewire from its beginnings. “Doing things as a platform, doing things in an open way, and doing things in a way that brings the community and the ecosystem along for the ride,” he said.

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