Industry Insights

CIO Classified: The back-to-basics guide to the future of work

With technological innovation accelerating faster than ever—and the pandemic entering a new phase—CIOs have never faced more uncertainty and complexity. That’s why we’ve partnered with Caspian Studios to sponsor Season 3 of the CIO Classified podcast. 

CIO Classified is a podcast for CIOs, decision-makers, and technology leaders that want to push their business forward and stay on the cutting edge. Each episode features candid conversations with leading CIOs discussing their most pressing challenges and how they solve them. 

Listen to the latest episode for insights and actionable strategies that you can bring back to your own organization today.

Episode summary

In this episode, Pure Storage’s CTO Rob Lee and Cengage Group’s CIO Jim Chilton discuss: 

  • Impacts of the overnight shift to remote work
  • Overcoming obstacles when undergoing digital transformation
  • The benefits of prioritizing security when designing infrastructure
  • How to scale up quickly and securely
  • Predictions for the future of work 

Episode soundbites

“Almost overnight the pandemic caused us to rethink what we were doing in some areas and redouble our efforts in what we’re doing in other areas…On certain types of work, meaning if I’m heads down and cranking on my project, I actually feel more productive. Where we started to see a little bit of slippage, if you will, was the cross-team collaboration or awareness of what’s going on outside of your team and in teams that you are maybe adjacent or lateral to…A large part of this is really about having good plans in place to keep newer employees super connected.” — Rob Lee, CTO at Pure Storage

“I would encourage people to be considerate of the cross-functional challenge, particularly being able to connect with people and not lose sight of that through this remote work I think is really important. We’ve implemented some of those fundamentals required now, so that you remove the ambiguity that the distance has created.” — Jim Chilton, CIO at Cengage Group

“Navigating transition has been the job of everybody on the leadership team, from the CEO all the way on down, because you’ve got to communicate context. You’ve got to get people to buy into that mission, that shift, and then believe in the philosophical changes that have to be evolved at every level in the organization. Along the way, there’s context and communication. There’s also a bit of an evolution in how decisions are being made.” — Rob Lee, CTO at Pure Storage

“Technology is the enabler to just about every company on the planet today. And that means CIOs are now the architects. I would encourage executives to really think differently about the lens of that technology executive and the contribution they can make to the strategy of the business that they’re trying to operate, the products they’re trying to create, and the customers they’re trying to serve.” — Jim Chilton, CIO at Cengage Group

Episode guests

Rob Lee, CTO, Pure Storage

Rob Lee serves as Chief Technology Officer (CTO) at Pure Storage, focused on global technology strategy, and identifying new innovation and market expansion opportunities for Pure. Rob joined Pure in 2013 as part of the FlashBlade founding team and led the software architecture and development, from concept to launch, for the product which has eclipsed $1B in business.

Prior to Pure, Rob was an Architect at Oracle, where he worked on programming language runtimes for the Oracle RDBMS, as well as high-performance distributed transaction processing systems. During his 12-year tenure at Oracle, he focused on improving the performance, reliability, and programming models behind large-scale distributed systems. Rob holds over 75 patents in the areas of distributed systems, language runtimes and storage systems.

He currently serves on the board of directors for Bay Area Underwater Explorers and Cordell Marine Sanctuary Foundation—nonprofits dedicated to the exploration and conservation of Northern California underwater resources.

Jim Chilton, CIO, Cengage Group

Jim Chilton is the Chief Information Officer (CIO) at Cengage Group, a $1.4B global education and technology company based in Boston. He is responsible for driving Cengage’s digital transformation and building successful internal technology roadmaps, including the launch of the company’s first subscription offer; Cengage Unlimited.

With 25+ years of experience in both startups and larger businesses, Jim has driven technology and business system innovations throughout his career. He is a five-time CIO, holding executive-level positions at several technology companies including Dassault Systemes, SolidWorks,, and IBM Maximo Consulting.  

In his spare time, Jim is an active advisor to several Boston-based startup companies, including Apprenti, Actifio, Cloud Zero and was an advisor and investor in SimpliVity prior to the acquisition by HPE.

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