Leading Transformation: Finding Your Voice in the Age of AI | Chandra Callicutt

What does it actually take to lead transformation — not talk about it, but do it repeatedly, at scale, across some of the world’s most complex technology organizations?

Chandra Callicutt has had the word “transformation” in her last three job titles for a reason. From IBM in 1996 to VP of CRM Engineering and Transformation at Cisco today, she has built a career across sales, marketing, IT, and engineering — and developed a sharp point of view on why transformations stall, where real resistance lives, and how people can stay relevant when the ground is constantly shifting.

In this episode, we cover her framework for moving fast without a roadmap, why she calls perspective the number one career multiplier, how the +D leadership program is helping her team define their legacy, and what she would say to anyone quietly pulling back from their career because they are waiting for the AI wave to pass.

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