CIO In The Know – What is top of mind for CIOs heading into the second half of 2026?

The latest CIO In The Know newsletter emphasizes the evolving discussions among CIOs, particularly focusing on customer experience, employee experience, and business operations. AI continues to be a relevant topic, with a shift toward balancing opportunity and risk. There's growing concern about AI-driven cybersecurity threats and an advancement in quantum computing, highlighting new opportunities and challenges for enterprises.

The CIO runs a marathon, not a sprint with Ellora Sengupta

In this podcast episode, Tim Crawford interviews Ellora Sengupta, CIO of EverCommerce, discussing the growing importance of AI councils in organizations. Ellora shares insights on transitioning AI from concept to implementation, her leadership evolution, and managing team dynamics. She emphasizes maintaining a work-life balance while transforming business through technology.

CIO In The Know – Continuing the Velocity – Insights That Move CIOs Forward

Happy New Year! 2026 kicks off with a bang…and a long list of subjects to cover. The CIO Playbook for 2026 is out and covers a wide gamut of topics CIOs are facing in 2026. TL;DR: It’s more than AI and technology.…

Counterintuitive thinking, the chief context officer and creating space with Eduard de Vries Sands

In a recent podcast, Eduard de Vries Sands, CIO of EVERSANA, discusses the evolving role of CIOs towards becoming Chief Context Officers. He emphasizes the importance of a product operating model focused on business outcomes, reducing reliance on traditional IT management, and fostering a culture of innovation and learning within teams to drive value.

How life as an inverted tree leads to technology optimism with Gaurav Singal

In this podcast episode, Tim Crawford interviews Gaurav Singal, CTO of Cantaloupe, who discusses his unique perspective on life and technology through the metaphor of an inverted tree. Gaurav emphasizes the necessity of understanding the business and customer service roles to foster innovation and balance risk with optimism, particularly in technology adoption.

The importance of people and how not to be a mushroom with Cindy Stoddard

This week's CIO in the Know podcast features Cindy Stoddard, Adobe's SVP and CIO, discussing the evolving role of CIOs in the AI era. Key topics include addressing past technical debt, the importance of infrastructure, work-life balance, and fostering a people-centric culture. Cindy emphasizes the significance of curiosity and strategic human connections in leadership.

CIO In The Know – AI or not to AI. That is the question…and how.

It seems every conversation touches on AI. AI is everywhere. At the same time, CIOs and CEOs are growing in their fatigue with AI conversations. Part of the problem is that vendors are adding ‘AI’ to everything and making it hard to…

CIO In The Know – CIOs, Buckle Up: The First 120 Days of 2025 Just Redefined Your Roadmap

The first four months of 2025 have significantly altered the CIO landscape, emphasizing the need for transformational leadership amid disruptions in AI, governance, and cybersecurity. CIOs are now focusing on data strategy and emerging AI agent discussions while grappling with complex regulatory environments. A mid-year Playbook update may be necessary to navigate these changes.

CIO In The Know – The multiple ways AI is maturing and CIOs are shifting gears into other subjects

Starting the last two months of 2024 takes us into a maturing of the AI conversation with both vendors and enterprise alike. Investment in AI continues for both as well.  Enterprises are largely moving from an experimentation phase to finding…

CIO In The Know – Mapping the CIOs second half of 2024

As we start the second half of 2024, a number of items are on the minds of CIOs including AI PCs, VMware, AI and data. As if that wasn’t enough, there are incoming regulatory requirements alongside political and economic instability.…