VentureBeat
by James Thomason
Retail resurrection: David’s Bridal bets its future on AI
Long-form feature on the Pearl Planner rebuild after a double bankruptcy — quoted throughout on the architecture and the bet behind it.
Currently — Head of Product & AI, David’s Bridal · Building Pearl Planner
BROOKLYN, NY · EST. 2010
I build AI products.
I lead the teams that ship them.
Product leader specializing in AI-native products. Head of Product & AI at David’s Bridal, building Pearl Planner. Previously Automattic (WooCommerce, Blaze), EIG (Luster.ai), 10up, DocuSign. Advised Google, Microsoft, Meta, Starbucks.
P
Currently building
Pearl Planner — an AI-native wedding planning platform at David’s Bridal.
Selected work
The portfolio is navigable by skill.
Twelve years of shipped work across AI, ecommerce platforms, ad marketplaces, and publishing systems. Open the work explorer and filter by the skill you care about.
~/writing $ ls –recent
Writing
& thinking.
Essays, podcast appearances, and bylines on AI-native product work, MCP, evals, and the craft of shipping with agents. Home base is the Leading Product newsletter, out Sunday mornings.
// subscribe
Sunday mornings
One essay on building AI-native products — evals, MCP, prompt infra, the operator’s view.
› essays [recent]
-
$ featured
I Overlooked Agent Skills
For a long time, I didn’t get them. What a Skill actually is, how to build, structure, and edit one without burning a week of usage, and the four kinds I’d build first.
-
Pearl Planner — The AI Native Platform for Wedding Planning
Role: Head of Product & AI | Company: David’s Bridal | Type: AI-native platform, 0-to-1 build. Planning a wedding isn’t a pain point —…
Read →
-
Wedding Color Studio — Helping Couples See Their Whole Wedding in Their Colors
A David’s Bridal-branded React + Gemini app that turns a five-color palette into a named identity, a generative editorial mood board, a six-scene vision…
Read →
-
Build a Composable AI Operating System
Building Your Personal Command Center Learn how to become a 100X PM with a composable tool stack you can run from your favorite AI…
Read →
› podcasts & interviews [selected]
The Artificial Intelligence Show
with Mike Kaput
How David’s Bridal is rebuilding a 76-year-old business around AI
Episode 240, with Elina Vilk — the “aisle to algorithm” strategy, the vision quiz and dynamic budgeting behind Pearl Planner, and Pearl Connect on Google Cloud.
Product Growth Podcast
with Aakash Gupta
How to build an AI-native PM operating system
Live demo of the composable AI operating system — Claude Code inside Cursor, with JIRA, Figma, Confluence and GitHub wired in over MCP.
› bylines [archive]
Endorsements
What the people I’ve worked with actually say.
Six of twenty-nine, verbatim and dated. Managers, peers, and the people who hired me — the full set is on the endorsements page.
What my managers say
Mike is the rare product leader who can shape a vision, ship 0→1, and then teach the rest of the org to do the same. Every team I’ve put him on has come out sharper.
Jake Miller · President · Engineered Innovation Group
He took on Woo Express when it was still ideas on a wall and turned it into one of the cleanest product launches we’ve shipped at Automattic.
Mary Hubbard · VP of WooCommerce · Automattic
Mike sees the product, the team, and the business as one system. That’s vanishingly rare.
Grant Landram · President · 10up
What my teams say
He’s the manager who will both raise the bar and clear it for you. I learned more in two years working for Mike than the previous five.
Eric Binnion · Senior Product Manager · Automattic
Calm in the room, fast on the keyboard, sharp on the strategy.
Brandi Awbrey · Product Lead
What my peers say
If you want one person who can lead the AI product motion and make your existing PMs better at the same time — it’s Mike.
Beau Lebens · Head of Product · Automattic
I trust Mike’s read on AI more than almost anyone else’s in this industry.
Joshua Fisher · Founder · Yardstick