Podcast / CXO of the Future

Chet Mandair, CIO, Guidewire Software

Listen to the podcast here:

technology in business transformation


Technology is disrupting long-standing business models, and every sector is feeling its transformative impact. In this week’s episode, Gamiel talks with Chet Mandair, CIO at Guidewire, about his experience leading IT in a variety of industries, and about the role of technology in business transformation.

Before Guidewire, Chet served at Salesforce on the strategic advisory team, helping customers transform by creating modern digital experiences which leveraged human-centered design thinking. He previously served as Chief Information Officer at Good Technology/Blackberry and as the Vice President of Process Excellence and IT at SunPower.

Chet started his career with Accenture and served on various boards, including the Salesforce CIO Global Advisory Board. He’s a mentor at Alchemist Accelerator, an early investor, and serves his community as a pro bono Commissioner of Parks.


During his student years, Chet went to high school at a Catholic boarding school in Calcutta. And as a senior, he watched the movie Field of Dreams.

“I was like ‘Oh, my God, I’ve got to go to Iowa for my higher education!’ I had family and friends in California who wondered what I was doing, but I think it was one of the best decisions of my life. I think the Midwest is the right place for somebody coming from a different country.”

Chet completed his undergraduate work in three years and pursued an MBA at Bradley University in Peoria, a suburb of Chicago, on a full scholarship. He was one of the youngest MBA grad students because everybody in his class was a director or higher from Caterpillar. Bradley’s MBA program was popularly known as ‘Caterpillar’s MBA program as a large percentage and support came from Caterpillar.

“That’s how my journey began. After my first year, I got excited about what people were doing at Caterpillar. There were a couple of students from Accenture as well, and I got attracted to the world of consulting. So, after my first year in the MBA program, I applied to Accenture and received an offer to start post-MBA in their Chicago office.”

Chet started with Accenture in their San Francisco office in their strategy practice. He transferred to their Process Excellence practice in his first week as he was more interested in making the strategy come real vs. just formulating the plan. He spent approx. 10 yrs at Accenture, and this experience helped him shape his journey ahead on the corporate side.

“I was involved in some of the largest transformation projects in Silicon Valley at that time. Oracle was the biggest ERP package, so I did a lot of ERP transformation at Sun Microsystems, Cisco, EMC, and others. That’s how I got connected with technology and business transformation. I enjoyed figuring out how to reengineer processes and learning how to use technology as a strategic enabler to scale.”

One of Chet’s mentors was the CIO at SunPower, Jorg Heinemann, who encouraged Chet to leverage his re-engineering expertise and join the company. Chet was excited about the prospect of solar/alternative energy and the difference SunPower was looking to make in the world. Their goal was to double their revenue to a $2B revenue company in four years.
His role at SunPower started with process reengineering and was soon asked to take over IT and use technology to scale those processes.

After four years at SunPower, Chet was recruited by a unicorn called Good Technology. They were looking for a CIO who could help them get ready for the upcoming IPO, showcase Customer Zero and help secure and scale for growth. Good Technology was on-prem software, transitioning to a cloud subscription business. In his first three months, Chet took on an interim GM position supported by an exceptionally talented team to launch Good’s first Enterprise Mobility Management cloud offering with supporting e-commerce capability to drive revenue growth and automate order fulfillment. It provided an opportunity to learn the subscription recurring business model, how IT can help launch a new business model and the cloud mindset. And a chance to learn from excellent mentors Ron Fior and Christy Wyatt.

Blackberry eventually acquired Good Technology. And Chet, who was part of the Salesforce CIO Advisory Board, decided he wanted to learn more about the CRM digital transformation and joined Salesforce as part of their Innovation and Transformation Center. While at Salesforce, he met an ex-colleague working at Guidewire who recommended Chet for the CIO position as his prior experience and Guidewire’s cloud transformation seemed a good match.

“I joined and was excited to learn about their business model and platform transformation and how technology was going to play a role in that. I’ve been at Guidewire for approximately two years now. That experience from graduate school, getting excited about consulting, then learning about business transformation and how technology can be a strategic enabler for business, is what led to where I am today.”

Driving Innovation from a Leadership Standpoint

“My leadership style starts with my values and also includes things I’ve learned from some of my mentors such as Winston King and Mike Rosenbaum here at Guidewire:

  • Put the customer first, the company second, and the team third. There is no ‘I’ or ‘You’ or ‘Me’ in this equation
  • Transparency and communication are key
  • Have empathy and lead by example

And I think those leadership values are critical in terms of achieving the confidence of team members and giving them confidence and getting everybody excited to join the journey.”

Weaving an Innovative Leadership Style in the Insurance Market

“It’s inspiring to be learning something new about a new industry. I had prior experience in security, hi-tech, solar, and alternative energy before coming to Guidewire. And today, I’m still getting educated on property and casualty insurance. I think there is a massive opportunity within the P&C market itself.

Many of our large customers have been running self-managed software platforms in their data center. The new Guidewire Cloud is the platform P&C insurers trust to engage, innovate, and grow efficiently. It combines digital, core, analytics, and AI to deliver our platform as a cloud service, exciting in the insurance space and for us at Guidewire. We are excited to partner with the P&C insurers to help them with their digital transformation.

We also have to pivot our mindset internally as we become a Platform-as-a-Service provider. Previously we had major software releases every two years or so. But since our new CEO, Mike Rosenbaum, has been here, we have a cadence of major releases every six months.

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 or ‘run the business’). One is making sure you run the business right, ensuring that there are printers, laptops, networks, etc.

And then, as you go up the hierarchy, you need to ‘secure the business’ – with cyber designed and built into the foundation. These two layers are what I called ‘Foundational Must Haves.’
The next level is what I call digital optimization or renovate. It’s about optimizing processes and making sure data flows from one place to another – scaling and automating standardized global processes, maximizing productivity, focusing on employee experience, and optimizing costs (bottom-line focus).

At the top of the hierarchy is digital transformation. How do we build and contribute to new business and drive top-line growth? I believe it’s critical for CXOs today to help build up the new business’s vision, evolving from optimization to transformation. Business intelligence at every level of the hierarchy enables data-driven strategic and operational decision-making.
Gartner defines digital transformation as ‘Taking what we do today and leveraging technology to do it better, faster, cheaper and more effectively.’ To me, that is digital optimization. Gartner also defines digital transformation as ‘stepping out and creating something that doesn’t exist.’ So that’s back to Maslow’s hierarchy of need: Contributing to top-line focus and driving better customer experiences. That’s what we are trying to do here at Guidewire.”

Here are the four areas we are working on moving forward:

  1. Simplification and Scale: Taking our existing processes, automating them, and scaling for the future.
  2. Data Democratization: Supporting the organization to make business decisions based on data. Have anybody use data at any time with no barriers to access.
  3. Customer Centricity: Optimize what we do for our customers by supporting our employees to provide our customers’ experiences.
  4. Support Disruptive Innovation: Identify new business ideas and incrementally iterate and enhance our current state.
    Advice for Startups

“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 vs. pitching the features/benefits of their product. The critical question to answer is How does their solution augment the achievement of that business outcome?

The product must have essential table stakes enterprise requirements already baked before pitching with the CXO/team.
Be flexible and ask yourself: ‘Is this the outcome they’re looking to accomplish? Is this an existing budget line item which may benefit?’ If it’s an existing budget line item, then it’s a much easier conversation.

Some groups have separate innovation centers and try to have that small group innovate and then bring that back to operations. In my experience, that doesn’t work very well. You need to encourage innovation and embed innovation in your everyday operations within your org.”

The Importance of Mentoring Startups

Chet thinks that the community needs to encourage and embrace innovation, create time and give back, especially in Silicon Valley.

“This is something I enjoy because it keeps me current on what technology changes are happening. At the same time, I can provide mentorship. In my case, my Friday afternoons from 3:00 p.m. to 6:00 p.m. are devoted to providing mentorship to entrepreneurs. It is my way of giving back. Some are successful, some fail but learn from their experience and come back on the second go around and thrive.

I think it is upon us to create time, create space, and give back, to create opportunity.”


  1. Understand the business and the vertical the company is operating in.
  2. Put the customer in the middle and design processes and experiences around the customer. Put the customer first, followed by the company. What can the company do to provide an incredible experience for a customer?
  3. Customer-first, company second, team third.
  4. Have empathy and lead by example. It has been especially crucial during the pandemic. And the pandemic has also proven that we can all work from anywhere.
  5. Find good mentors, people who have seen the movie before, or people who can pull you aside and share their experiences or ideas.

About Chet

Chet Mandair is Chief Information Officer at Guidewire Software. In this role, he oversees Guidewire’s global Business Technology organization to support the company’s growth and remote-first working modality by delivering delightful, safe, connected experiences for our Guidewire community. Most recently, Mandair served at Salesforce on a strategic advisory team, helping customers transform by creating modern digital experiences leveraging human-centered design thinking. He previously served as a Chief Information Officer of Good Technology/Blackberry and the Vice President of Process Excellence and IT at SunPower. Mandair started his career with Accenture and served on various boards, including the Salesforce CIO Global Advisory Board.

Mr. Mandair is a mentor at Alchemist Accelerator, an early investor, and serves his community as pro bono Commissioner of Parks.

Join The CXO of the Future Community today:

You May Also Enjoy