Cabi’s AI-First Transformation: How One Fashion Brand Turned Curiosity Into Capability
This week, our AI-First community welcomed a special guest: Keith Fairclough, CIO at Cabi, the modern women’s fashion brand redefining what it means to build an AI-First organization.
Today, nearly everyone at Cabi, from designers to finance, uses AI daily. Here’s how they got there, plus two real examples Keith demo’d during the call that just might spark ideas for your own AI-First journey.
Unlocking an AI-First Organization
Cabi’s AI journey began quietly. In early 2023, a handful of marketing team members started experimenting with ChatGPT for writing and creative brainstorming. Within months, Keith realized something powerful: the real unlock wasn’t the technology, it was literacy.
“We didn’t start by building apps,” he shared. “We started by making sure everyone understood what AI could do for them.”
That mindset set the tone for the entire company.
Every employee received hands-on training.
At first, many said they were “too busy”, so they had the training in person. By the end of session, nearly everyone had a task they wanted to try with AI.
Nine months later, 96% of Cabi employees were using AI three or more times per day.
Weekly “AI office hours” and monthly GPT challenges helped keep momentum and curiosity alive.
Concerns about security or job displacement were met head-on with a simple message:
“AI is here to amplify you.”
Keith’s goal was clear, to make AI feel personal, practical, and empowering.
Building with AI
Once the foundation was set, Cabi moved from learning to building. In true Cabi fashion, the breakthroughs came not from vendors or massive budgets but from small teams experimenting and solving real problems.
The AI Styling Tool
An intern with a masters in machine learning built the first version of Cabi’s AI-powered styling assistant, now known as The Outfit Studio, in just three weeks.
The tool integrates with Cabi’s Shopify commerce platform and Snowflake data warehouse to:
Generate three complete outfit recommendations at a time
Mix new items with each client’s “closet” (past purchase history)
Deliver shoppable links stylists can text or share with clients
Stylists can even upload customer photos to visualize outfits with a 95% accurate rendering that feels personal and intuitive.
“We built this ourselves — not a vendor solution,” Keith said. “That’s what being AI-First means. Building tools that reflect how we work.”
Leveraging Lovable
When Cabi needed to train stylists on a new Shopify point-of-sale system, Keith decided to “vibe code” a solution.
Using Lovable, a generative coding platform, he built an interactive, gamified training app in under four hours. No engineering tickets. No expensive learning management system. Just natural-language instructions and AI-assisted creation.
The app guides stylists through key tasks in an interactive prototype, like setting up accounts and processing sales, in a visual, clickable format that’s easy to follow and fun to complete.
“It was faster, more engaging, and more personalized than anything we’d built before,” Keith shared. “And it showed our teams they could build too.”
Cabi plans to expand the concept by creating a library of mini-training apps for onboarding, selling, and styling workflows.
Lessons for Leaders
Cabi’s story is proof that AI transformation doesn’t require massive budgets or big teams. It requires a growth mindset, experimentation, and trust in your people.
Here’s what other leaders can learn from their journey:
1. Literacy unlocks innovation.
Before tools or pilots, focus on understanding. Once people know what AI can do, ideas emerge naturally.
2. Build internally whenever you can.
Cabi’s most impactful tools, from the styling assistant to the Lovable training app, were built by their own employees, not vendors. When teams are equipped with the right AI tools they are able to create their own solutions, they move faster and design exactly what they need.
3. Culture drives adoption.
Cabi reframed AI as a superpower, not a substitute. That shift in mindset helped employees lean in with curiosity instead of fear and made AI part of everyday work.
4. Invest in experimentation before ROI.
AI progress starts with permission to play. Give your teams room to explore, fail fast, and share what they learn. The creativity and confidence that follows will drive impact far beyond the expected ROI.
5. Try what you can, where you are.
You don’t need to code to build. Tools like Lovable, Claude Code, and Cursor AI now let anyone experiment with creating their own ideas and solutions.
“Becoming AI-First isn’t about adding one more tool,” Keith said. “It’s about giving people permission to build and removing the fear of trying.”
Closing Thought
Cabi’s AI-First foundation didn’t begin with data or tools, it began with a mindset. A belief that curiosity, experimentation, and empowerment fuel real change.
And as Keith put it best:
“When people stop waiting for permission to use AI, that’s when transformation really begins.”
A huge thank-you to Keith Fairclough for sharing his journey, his insights, and his optimism about what’s possible when people are empowered to build.
Missed the call? No worries, we’ve got you covered!
Just reply to this email and we’ll send you the full recording. It’s a must-watch (we’ve had our best feedback yet from those who joined live).
And stay tuned! We’ve got more incredible sessions coming soon, featuring brands and leaders who are redefining what it means to be AI-First.