The work is never really about the product. It's about the org structures, ownership models, and measurement failures that produce fragmented experiences and wasted engineering. I've spent a decade building at organizational scale inside one of the world's largest retailers. Now I'm building from the outside.
I've been developing these ideas in public since 2011 — GOTO Zurich, ConnectJS, Supernova South, 35+ workshops and courses at General Assembly. Here's where the conversation is now.
See all writing →Previously: GOTO Zurich · ConnectJS Atlanta · Supernova South · Black Founders Conference · SoundBoard · General Assembly (first courses in Atlanta, 2014) · Fortune 500 consulting: Disney, BB&T, Lockheed Martin
It's a real operating entity with active ventures. The same point of view that shaped a decade of enterprise work — organizational behavior as a design problem — now applied from the outside.
The portable context layer. One system — not a patchwork of GitHub and Notion — readable by any model, owned by you. What AI-assisted work runs on when the session ends.
Fifty-two essays on why work gets stuck when good ideas collide with priorities, incentives, politics, and incomplete information — and where you have leverage to move it. Not another methodology. Use it when the work gets real.
Audio learning for working professionals who need depth, not noise. Dual-mode platform — long-form and pulse-format — designed to meet people inside the time they actually have.
An AI talent agency built on a different incentive model. 90-day pay structure aligns the interests of talent and placement organizations — instead of optimizing for the transaction, it optimizes for the fit.
I started doing this work before I had a name for it. The instinct — that most design problems are actually organizational problems in disguise — showed up early. In 2011 I co-founded TripLingo, built a multi-platform language learning app in six months, and raised $2.35M. We were moving fast, and the places we got stuck were never the design problems. They were the conditions around the design problems.
A decade at Home Depot gave me the scale to test the thesis at organizational weight. I wasn't just running the portfolio — I was in it… shaping the conditions inside it. Managing teams & amazing practitioners. Influencing fifteen or more cross-functional partners. Delivering on major initiatives like the No New Apps strategy. The Experience Metrics & Journey Management System. Improving our customer Returns, as well as our taking ownership of our last mile services in Supply Chain to deliver maximum customer value. Each one was an argument made at organizational scale — not a deliverable, not a project. A changed condition.
Now I'm building from the outside — Baskerville & Co. as the operating entity, with a set of ventures that apply the same thinking to different problems. And I'm stepping back into the public conversation after years of deep internal work. The ideas were always developing. Now so is the writing.
Both audiences are buying the same thing: executive-level thinking applied to complex organizational and product problems. The difference is the form it takes.
If you're building or rebuilding a design or product organization — and need someone who has done it at scale, with the organizational scar tissue to match — I'm open to the right conversation. I've led at portfolio level, influenced without authority across 15+ cross-functional teams, and built governance where none existed.
Let's talk →If you don't need to hire direct — but the problem still needs someone who's done this at scale — that's what Baskerville & Co. is for. Strategy through execution, facilitation, embedded design and product work. Small number of engagements each quarter, by design.
Start the conversation →