Guidewire CEO Coaxes Customers to Embrace Cloud

At the Connections customer conference on Oct. 24, Mike Rosenbaum stressed the logic of Guidewire innovating in the cloud and the ‘illogical’ choice to invest in innovation on-premise.

(Mike Rosenbaum, CEO, Guidewire, during Connections 2022 keynote on Monday, Oct. 24. Source: Guidewire.)

In his keynote address during the general session at Connections 2022 at the Aria Resort in Las Vegas on Oct. 24, Guidewire CEO Mike Rosenbaum stressed the importance of customers embracing consumption of the vendor’s software in the cloud. During the address, Rosenbaum introduced Flaine, the latest Guidewire Cloud release. Since Rosenbaum took on the CEO role at Guidewire in 2019, he has driven the company’s commitment to new cloud releases ever six months. As Guidewire CMO Brian Desmond noted later during the general session, the cloud releases transform use of Guidewire’s software “from upgrades to updates.”

“We see, with 100 percent certainty, a future in which every single one of our customers is operating on guidewire cloud,” Rosenbaum said. “We made a commitment to do this a few years ago to get started, and we’re on this journey but I think it is now very, very clear that the that this affords us a mechanism to deliver so much more value to our customers that we truly believe we will get to the point where 100 percent of you are running on Guidewire Cloud.”

Rosenbaum expressed misgivings about customers continuing with on-premise (on-prem) instances of Guidewire’s products as making it increasingly untenable for the software company to innovate and invest in the on-prem version. He described the cloud as a much more efficient mechanism for the company to deliver value to its customers and characterized the cloud as Guidewire’s direction for the future. “It’s where we’re going, and so each of our choices ends up landing us in the decision to put that product in the cloud,” he said.

Customers remaining on-prem was problematic for another reason, Rosenbaum continued, touching on the complexity created by multiple modifications that stray from the software as written and as updated in a universally accessible and consistent version in the cloud. “The other side of this, which is probably more important—and maybe a little bit uncomfortable but I believe needs to be said—is that your investment in your on-prem implementations of Guidewire I would say is now slightly illogical,” he said.

“Each and everything you’re doing with your on-prem implementation of Guidewire is just slightly wrong,” Rosenbaum elaborated. “We’re going to make sure that you’re successful, but when you create or change a product it’s done in a slightly different way. When you create or change an integration, it’s done in a slightly different way; when you create a customer experience, it’s done in a different way.

Better in the Cloud

All of a given customer’s investments should be calculate against how customers could be implementing them if they were doing so more efficiently in the cloud, Rosenbaum insisted.

“I want to make it crystal clear: we’re going support this customer base, and we are completely committed to doing that,” Rosenbaum qualified. “But it’s also appropriate for me to call this out and say that there is a better way to do everything that you are doing with Guidewire in the cloud.”

Guidewire Announces Flaine Cloud Release at Connections Conference

Anthony R. O’Donnell // Anthony O'Donnell is Executive Editor of Insurance Innovation Reporter. For nearly two decades, he has been an observer and commentator on the use of information technology in the insurance industry, following industry trends and writing about the use of IT across all sectors of the insurance industry. He can be reached at or (503) 936-2803.

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