Learning AI Together: Inside Cabiʼs Transformation with CIO Keith Fairclough

AI First with Adam and Andy

In this episode of AI First with Adam and Andy, we’re joined by Keith Fairclough, CIO of Cabi, a women’s apparel brand with a national network of over 2,000 independent stylists. Keith walks us through how he went from early AI experimentation to spearheading a full-scale transformation at Cabi, turning curiosity into capability across the entire company.

Keith breaks down the lessons from their AI bootcamp with Forum3, the structure they built to scale adoption (including org-wide training, AI office hours, and GPT competitions), and real use cases now saving time and expanding output, from automated marketing retouching to a custom GPT for IT sprint planning. He also shares what didn’t work, including missteps around executive involvement and building out an AI champions team.

If you’re a leader looking to scale AI across your organization, not just implement tools, this episode offers a front-row seat to what it looks like to lead with vision, structure, and practicality.