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Profile summary

Chet Mandair is a forward-thinking tech leader with 20+ years of experience driving digital transformation across industries, from enterprise tech and solar energy to cybersecurity and insurance. Currently CIO at Guidewire Software, he leads global technology initiatives focused on cloud modernization, agile execution, and AI-powered innovation.

Under his leadership, Guidewire became a 100% cloud-based enterprise, adopted agile product delivery, and embedded AI and analytics into operations to elevate both employee and customer experience.

He is committed to using AI and emerging tech not just to scale operations, but to shape resilient, people-centered digital enterprises.

Connect with Chet on: LinkedIn

Career highlights 

2019
Chief Information Officer
2016
Head of expeditions
2014
Chief Information Officer
2009
VP of IT & Process excellence
1995
Senior Manager

Claim to fame

Emphasis on digital employee experiences

Chet Mandair is continually focused on shaping seamless digital employee experiences, especially in a hybrid work environment at Guidewire. While their IT landscape has plemnty of digital collaboration and communication tools, Chet is focused on designing frictionless, fatigue-free experiences that supports real-time problem-solving. Mandair envisions a work environment where the tech disappears into the background, and what remains is an intuitive, integrated experience that fosters employee productivity.

Driving infrastructure modernization

One of Chet Mandair’s most impactful initiatives as CIO at Guidewire is the company’s transition to a 100% cloud-based infrastructure. This move unified Guidewire’s digital ecosystem across tools, platforms, and services, now delivered via cloud and SaaS. The transformative shift laid the company’s foundation for scalable and agile operations globally.

Embedding a data-driven culture

At Guidewire, Mandair underscored the importance of data analytics platforms to democratize access to data that is continuously updated and easy to use. He enabled Guidewire to prioritize a dynamic, data-driven culture, moving away from manual spreadsheet tracking to interactive dashboards, and real-time data experiences that inform decision-making across the company.

Chet's AI philosophy

Chet Mandair
CIO, Guidewire 

"It isn’t easy to describe what IT does within a company. The easiest way to describe it might be through Maslow’s hierarchy of needs. At its core, there is foundational stuff we have to do for all of us (keep the lights on). And then, as you go up the hierarchy, you need to ‘secure the business’ – with cyber designed and built into the foundation. At the top of the hierarchy is digital transformation. How do we build and contribute to new business and drive top-line growth?" Source

“Innovation is vital for us as a community. We need to support and embrace innovation. The key for entrepreneurs, especially in the enterprise space, is understanding and empathizing with customer’s needs and how their product helps deliver the business outcomes Source

“The role of technology is to help deliver those experiences that make it simpler and automated, and so this is just a natural progression … at the end of the day, you want to provide a seamless employee user engagement and provide the right tools so [they] can be successful in doing their role.” Source

Awards and accolades

Wire19’s Top 100 US CIOs 2023
Lumos Top 50 CIOs 2023
Bay Area CIO of the Year ORBIE Awards finalist 2021

What does it take to be an AI Champion? 

We’re not looking for trophies. We’re looking for trailblazers.

You’re an AI Champion, if you’ve: 
Implemented AI in the real world not a pitch deck.
Driven change across teams, even when it wasn’t easy.
Led from the front, helping your org rethink how work gets done. 
Sounds like something you’re doing right now? 

Tell us about your AI work