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informationweek

2026 tech company layoffs InformationWeek Podcast: CTOs on using AI in regulated spaces How top CIOs are measuring the real ROI of IT automation What AI must learn from Roosevelt, conservation and 1929 Experian's chief innovation officer gleans AI gains with startup collab ETS CIO on competing with AI startups 'running with scissors' Before the next VMware: How CIOs prepare for vendor shocks The strategic alignment powering cyber-resilient organizations The AI infrastructure bottleneck is becoming a CIO problem InformationWeek Podcast: CTOs on reining in rogue AI agents Workplace equity in the age of AI Why and how to implement an AI asset rationalization strategy Why companies are shifting toward private AI models AI agents in automation: When to build, when to buy Navan CTO AI on trial: The Workday case that CIOs can The AI infrastructure boom is coming for enterprise budgets How CIOs can manage LLM costs: A practical guide What CIOs miss when buying vertical SaaS software InformationWeek Podcast: How CTOs balance AI and their teams Whirlpool, Duke Energy, Cleveland Clinic CIOs on scaling AI Where CIOs get stuck rebuilding the enterprise: What 'Rewired' reveals As AI makes projects harder to track, will CIOs need new controls? Why disaster recovery plans fail in geopolitical crises A silent erosion of enterprise AI by data poisoning Priceline CTO prioritizes engineers able to 'hold a room and a roadmap' InformationWeek Podcast: When CTOs need to restart IT projects Wayfair CTO maps agentic path across digital and brick-and-mortar commerce The AI contract gaps the Google-Pentagon deal just made visible Non-human identity sprawl is agentic AI's real risk Anthropic's Mythos forces a rethink of vulnerability management Outsourcing contracts weren't built for AI. CIOs are renegotiating now The AI spend hangover companies didn't plan for The power of CIO networking in the competitive AI world Why CIOs see AI projects stall: Speed without structure kills scale IT leaders should never let a good crisis go to waste SFO's digital twin maps airport operations from the curb to takeoff CIOs caught in the middle as AI startups disrupt vertical Saas Submit an IT Leadership column to InformationWeek Podcast: Rightsizing AI frameworks to avoid failure modes The invisible labor crisis inside IT: AI work the org chart can't see Why AI teams treat training data like capital Ask the Experts: How CIOs can identify and overcome cultural barriers to innovation Nobody told legal about your RAG pipeline -- why that's a problem Meta's new 'AI Zuckerberg' is a mirror for every C-suite Will the music stop for AI's funding dance? 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Your AI vendor is now a single point of failure Vibe coding: Speed without security is a liability A practical guide to controlling AI agent costs before they spiral AI fuels a new wave of technical debt The sunsetting of Sora: A hard lesson in AI portfolio resilience HP pushes broad internal AI use after early productivity gains Why value-based pricing is inevitable InformationWeek Podcast: Safeguarding ecosystems from outsiders Why AI scaling is so hard -- and what CIOs say works Humans are the North Star for AI-native workplaces -- Gartner How IT leaders build a culture for what comes next Compliance costs risk widening the AI gap AI-driven layoffs add new demands on CIOs to prove value AI transformation: Early wins are not enough for CIOs Why CIOs can't let users wait on IT Memory shortage doesn't have to spell disaster for IT budgets Accelerate AI adoption: 3 reasons for adopting MCP How techno-nationalism is complicating IT resilience and supply chains for CIOs InformationWeek Podcast: Compliance crackdown on AI and BYOD Workday’s AI reset: Agents and the race to remake SaaS Why enterprise AI initiatives keep dying before production Metrics of meaning: What do we really measure in AI? Techno-nationalism is reshaping CIO infrastructure strategy Using AI to pick team leaders -- without crossing legal or ethical lines What Oracle's layoffs reveal about running IT with fewer people Chief AI Officer on course-correcting when AI moves too fast Large enterprises need high-performing networks to scale AI InformationWeek Podcast: When do smaller AI models make sense? The future belongs to AI-driven IT Ways AI supercharges risk awareness and data insights for CIOs How automation prepares you for agentic NetOps Should the CIO, CFO or CEO hold the kill switch on AI? The CIO's new mandate: Redesign work itself Ask the Experts: CIOs say they wouldn’t pull workloads back from the cloud How AI is Reshaping the Enterprise
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]