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informationweek

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InformationWeek Podcast: CIOs on backing uncertain tech bets
Joao-Pierre S. Ruth · 2026-05-29 · via informationweek

Introducing and scaling up new technology can come with a cloudy path to results, leaving CIOs, CTOs and CISOs to champion the potential benefits. 

Advocating new tech with uncertain ROI does not mean ignoring questions from other C-suite leaders. How CIOs pick their battles, and the roadmap they present, can make the difference when the technology does not deliver clear, immediate results for the company.

In this episode of the InformationWeek Podcast, Heather Hinton, CISO at Sitecore, and Richard Mackey, CIO at CCS Medical, discuss their approaches to advocating for their tech bets.

CCS Medical is a medical supplies and chronic condition management company. Sitecore is a provider of web content management and marketing automation software.

The world obviously wants to see real ROI from AI. In the episode, Hinton and Mackey discuss how easy or difficult it is to sell AI to support and other technologies within their organizations.

Related:The CIO's next job: Leading business change with the CEO

They also discuss how they set timelines for technology to prove its worth, how they handle CFO questions about tech investments, and which cautionary stories guide them as they put technology through its paces.

Mackey and Hinton then bring their experience to the Questionable Ideas tabletop exercise to help the fictional company work through its uncertain tech bets.

About the Author

Joao-Pierre S. Ruth

Senior Editor, InformationWeek

Joao-Pierre S. Ruth edits stories for InformationWeek as well as reports on C-suite tech leaders across a multitude of industries and tech disciplines. He also hosts the InformationWeek Podcast, which brings together CIOs, CTOs, and other C-suite leadership to discuss their different approaches to addressing shared challenges. He joined InformationWeek in 2019, initially as a Senior Writer covering cloud computing and DevOps. He became a Senior Editor in 2023.

His work with InformationWeek garnered American Society of Business Publication Editors (ASBE) awards in 2024. This included "Could the DOJ's Antitrust Trial vs Google Drive More Innovation?" as part of the team’s Government Coverage, which collectively won a Bronze National award and a gold Northeast regional award, as well as a bronze regional award for a Web Feature Series on the environmental impact of data-driven organizations published during Earth Month. That award included his story "How Do Supercomputers Fit With Strategies for Sustainability?"

He has been a journalist for more than 25 years, reporting on business and technology first in New Jersey, then covering the New York tech startup community, and later as a freelancer for such outlets as TheStreet, Investopedia, and Street Fight.

Joao-Pierre can be reached via email at [email protected]