I came in to reshape design. I ended up shaping how the company's knowledge workers use AI.
I joined a 30-year-old retail tech company with one designer, no design process beyond accessibility and a nascent component library, and a CEO who wanted AI strategy yesterday. I was hired to reshape the design department — I chose AI as the lever. That choice pulled me beyond pure design leadership into operationalizing AI for knowledge workers across the org: the people who actually had to use these tools to do their jobs needed upskilling, workflow redesign, and patterns that worked.
What I walked into
A 30-year-old codebase, hundreds of screens, one designer, and a department whose entire process consisted of an accessibility partner and the early bones of a component library. Meanwhile the CEO wanted AI strategy yesterday. The old way of designing — a Figma file per feature, one designer per screen, hand-off, repeat — wasn't going to scale, and bolting AI onto a broken pipeline would just produce broken output faster. So I stopped trying to make designers work faster and rebuilt the process around an idea I called provenance: every screen we shipped should know exactly where it came from.
The move
I built an 8-phase pipeline that runs from "we have a problem" to "we shipped, and here's what users did with it." Each phase produces an artifact, and every artifact carries a breadcrumb trail back to the problem brief that spawned it. Translation: any teammate can open any spec line in our repo and walk it back to the user research, the design decision, the dev review, and the analytics. Nothing is orphaned. Nothing gets lost.
AI does the heavy lifting where it's good — generating interactive HTML prototypes with edge cases, piping to Figma via MCP, transcribing dev/PM feedback into structured notes. Humans do the heavy lifting where we're good — judgment, edge-case storytelling, the conversations that don't fit in a Jira ticket. An external accessibility partner validates before lock. Production telemetry comes back in and teaches the next design.
What changed
A UI modernization that used to take three weeks now ships in one afternoon. Not because we're cutting corners — because the next designer doesn't have to re-derive the same decisions every time. The system remembers. The team adopted it; this isn't a one-designer party trick.
The clearest test was a webcart redesign: 200+ screens, scoped for 4–6 sprints, delivered with two designers — one of whom was leading the org. The same scope under the previous design model would have required at least two additional senior designers and, by my estimate, 6–8 months of effort. Neither was available. The system closed the gap.
See how the screen builder actually runs
Eight folders, six phases, the feedback loop, and a worked example with a decision-log excerpt — mocked into a neutral domain for confidentiality.
What was hard
AI-augmented design isn't a free lunch. Three things bit us, and shaped how I run the pipeline now:
- Pixel-perfect parity with an existing component library is brutal. Importing a mature library into Claude Code and getting prototypes to honor every token, spacing rule, and state variant — without the model quietly inventing a button — took significantly more guardrails than I expected. We solved it by tightening the prompt contract and treating the library as a constrained vocabulary, not a suggestion.
- Routing transcription into the right node of the knowledge graph requires slow, deliberate upfront work. Dev/PM feedback only stays useful if it lands on the spec line it actually addresses. That meant building the graph carefully, one stable connection at a time — moving fast here corrupts every downstream decision.
- Edge cases have to be documented before the agent can find them. Our webcart redesign turned into 200+ screens. The agent could only generate useful variants once the edge cases — empty states, error paths, partial-data scenarios, permissions branches — were written down somewhere it could retrieve. Documentation stopped being a deliverable and became infrastructure.
What it unlocked
Proving AI inside design earned the mandate to redesign how the company's knowledge workers use AI more broadly. That work became a 9-layer connected intelligence architecture — green-lit by the CEO and IT for company-wide scale. That's Case 05.