From Bootcamps to Shoppable Styling: How Cabi Built an AI First Culture and Shipped Real Tools Fast
CIO Keith Fairclough shares an inside look at Cabi’s AI First transformation, from executive bootcamps and companywide literacy to practical governance, office hours, and adoption metrics. He also demos two real builds: an AI styling and virtual try on experience created by a single intern in weeks, and a Lovable based interactive training prototype to prepare 2,000 stylists for a new Shopify powered POS.
In this inside look from an AI First community call, Keith Fairclough, CIO of Cabi, explains how a direct sales women’s apparel brand built AI literacy across the company before chasing shiny use cases.
He details the executive bootcamp that aligned leadership, the in person training that drove adoption, and the practices that sustained momentum, including weekly office hours and monthly AI competitions. Keith then shows what the foundation enabled: an AI styling tool that generates on brand outfits from the product catalog, creates shoppable flat lays, and can incorporate a customer’s closet history, plus an early virtual try on capability. He also shares how he used Lovable to create a clickable, gamified POS training prototype using screenshots, helping prepare 2,000 stylists for a Shopify rollout before go live.
Practical lessons on culture, governance, and shipping value fast.