The Agile CEO Evolution, Not Transformation With Jenny Wood, Group CIO at Skipton Group
In this episode of Season 2 of The Agile CEO, JJ Sutherland sits down with Jenny Wood, Group Chief Information Officer at Skipton Group, to explore what true agility looks like inside a 170-year-old financial institution — and why the most effective leaders see change not as a transformation, but as an evolution.
With a career spanning Telstra, NatWest, and now Skipton Group, Jenny has led large-scale change across financial services and telecoms — always grounded in a clear purpose: helping teams deliver better value faster. She’s guided organizations through cloud-native modernization, DevSecOps adoption, and enterprise-wide Agile evolution, all while keeping people and purpose at the center.
Jenny and JJ unpack what it takes to build learning organizations that adapt continuously, not episodically. Together, they explore:
Why “transformation” should be replaced with evolution as the mindset for modern leaders
How curiosity fuels better leadership, faster feedback, and smarter decision-making
Why measuring value, not activity, is the hallmark of agility
How Skipton is modernizing through cloud, data, and DevSecOps without losing its member-owned purpose
The overlooked power of designing colleague journeys, not just customer ones
Throughout the conversation, Jenny shares stories from her time leading teams across continents, revealing how clarity of purpose, disciplined curiosity, and small, continuous learning loops can reshape even the most established organizations.
If you’re an executive leading large-scale change, wrestling with legacy systems, or seeking to build a culture that learns faster than it changes, this episode offers a practical, human roadmap for evolving how your business works — and why it works.
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