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informationweek

2026 tech company layoffs How Sedgwick scaled AI in legacy claims workflows 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? 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InformationWeek Podcast: New IT architecture, cloud, edge and AI
2026-04-09 · via informationweek

The idea of transformation has blown past "simply" lifting and shifting to the cloud. Naturally, it can be easier for newer companies to go cloud-, edge- or even AI-native. It might not be so simple for established businesses to make these migrations, which can become even more complicated with AI.

In this episode of the InformationWeek Podcast, Steve Croce, field CTO of Anaconda, and Ravi Soin, CIO and CISO of Smartsheet, discussed what resources they found essential in the transformation journey at their companies. They also shared the hurdles that needed to be cleared to bring such resources into their architecture, and where there can be a bright side to the work that goes into transformation with AI, cloud and edge in the mix.

The Questionable Ideas tabletop exercise also returned, giving Soin and Croce a chance to collaborate and keep the resident goblins, kobolds and gremlins at the fictional company at bay.

Related:Who controls the fix? Colorado's repair fight tests CIO power

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 one CIO or CTO with a business-operations executive to discuss their different approaches to addressing shared challenges. 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.