How Guidewire Makes Cloud Migration Smoother and Faster — Without Starting Over

  • Don Williams, Senior Director, Head of Cloud Migrations, Guidewire

May 19, 2025

Guidewire Conversations - host Brian Desmond and guest Don Williams

If you’re running Guidewire on-premises today, moving to the cloud might feel like a big step. Some common questions we hear: What happens to the customizations and workflows we’ve built? Will the move disrupt our operations? Will it be more complex than it sounds?

The good news is it doesn’t have to be. With more than 80 migrations behind us, we know how to avoid major disruptions and make the move quicker and more predictable than you might expect. Our goal is to help you stay current and unlock new capabilities, while carrying forward the systems and strengths you’ve already built.

Here’s how we do it.

A Proven Migration Process

Migrating to the cloud doesn’t have to be overwhelming. At Guidewire, we use a clear, proven process that gives teams the structure, support, and speed they need to make the move with confidence.

Every migration is made up of three major phases:

  1. Technical Upgrade
    We kick things off by merging your self-managed InsuranceSuite code into the Guidewire Cloud Platform, bringing over what’s already working for your business. Our migration team, many of whom have over a decade of upgrade experience, handles the merge and works through any technical issues that come up along the way.
  2. Delivery
    Once the technical work is complete, a delivery team steps in. This could be Guidewire, your own team, or a system integrator (SI). About 70% of our cloud migrations involve working side-by-side with an SI to keep handoffs clear and projects on track.

    The focus here is on validating the upgraded InsuranceSuite application, checking for cloud readiness, and addressing cloud suitability issues to get ready for full testing. For example, direct database access or legacy code that worked on-prem may need to be adjusted for the cloud.
  3. Testing
    In the final phase, we test your entire application, including workflows, integrations, database validation, and performance. This phase helps spot and fix any issues before you go live, so everything works as expected once you’re in the cloud.

Faster Updates, More Flexibility

One of the biggest changes customers notice after moving to Guidewire Cloud is how much easier it becomes to stay current and tap into new features. On-premises upgrades can take 18 months or more — and by the time they’re complete, more updates could already be on the way.

In the cloud, that cycle looks very different:

  • Speed Without the Stress
    Each new cloud release brings regular improvements, but with much less disruption than lengthy on-premises upgrades. Updates are simply pushed to your environment and, after about a week or two of testing, you’re up and running.
  • Less Maintenance, More Strategy
    Guidewire manages the infrastructure behind the scenes — from servers to system maintenance — so your teams can spend less time on technical upkeep and more time driving the business forward.
  • More Control Over What You Adopt
    New features roll out several times a year, but you don’t have to take them all at once. Because updates are lighter and optional, you can choose what aligns with your business goals and adopt on your terms.

Early Planning Makes a Big Difference

Even if your migration is months away, taking a few smart steps now can make the process much smoother later.

Here’s how to get a head start:

  • Clean and Prepare Your Database
    Guidewire offers health reports that flag potential issues in your database. Fixing them early strengthens your on-premises system today and helps get your data ready for cloud migration down the road.
  • Get a Cloud Upgrade Estimate (CUE)
    A CUE gives you a clear picture of your InsuranceSuite setup’s cloud readiness. It highlights areas that may need updates and shows you exactly where to focus first, making it easier to plan your next steps.
  • Explore What’s New
    As part of the planning process, we can show you what’s changed between your current version and your target cloud release, including a breakdown of new and updated features. We also offer value alignment sessions to help map those updates to your business goals, so you know what’s worth adopting and when.

Ready for a Smoother Move?

At Guidewire, we help customers move to the cloud with a proven process, strong partner support, and years of experience. Every step we’ve built — from technical updates to migration support — is designed to make the journey quicker, more predictable, and less stressful.

And there’s more in the works. We’re continuing to invest in automation and AI to make migrations even simpler. Already, new AI models can fix many upgrade errors automatically, cutting work that used to take weeks down to just a few hours. And with upcoming tools, some integration and configuration changes will be even easier.

Wherever you are in your cloud journey, we’re ready when you are.


This blog is inspired by a conversation between Brian Desmond, CMO of Guidewire, and Don Williams, Sr. Director, Head of Cloud Migrations at Guidewire.

Hear how the experts are tackling insurance tech, cloud, and the industry’s biggest challenges. Check out our Guidewire Conversations series.