Lessons from 15+ AI engagements, two companies I co-founded, and 18 years of building products people actually use.
Stanford’s Digital Economy Lab studied 51 enterprise AI implementations and found the same pattern in every failure. Same technology, wildly different outcomes. The variable wasn’t the model — it was the organization. Here’s what organizational readiness actually means and how to know if your company has it.
The standard quarterly roadmap doesn’t work for AI products. Model capabilities shift faster than planning cycles. Here’s the framework I use instead — phased, ROI-scored, and designed to survive the chaos of a fast-moving AI landscape.
Shipping an AI hub is the easy part. Getting an entire company to change how they work is the hard part. Here’s the department-by-department rollout strategy that took us from pilot to company-wide adoption in 3 months.
I’ve watched companies spend 6 months building AI features nobody wanted. My rule: if you can’t validate the concept with a working prototype in 2 weeks, you’re solving the wrong problem.
I built Gleantap from $10K to $2M ARR and led a COVID pivot at Mastera that cut churn from 10% to 2%. Here’s how those founder scars make me a better AI leader — and what I’d do differently.
Your AI agent just accessed client data it shouldn’t have. Legal is asking questions. Here’s why AI governance needs to be designed at Phase 1, not bolted on at Phase 5 — and the framework I use for regulated environments.
How I mapped every AI opportunity for a DTC subscription brand — from customer service automation to predictive churn models — and built a roadmap their team could actually execute on.
The hardest part of shipping AI agents isn’t the model — it’s the trust gap. Users don’t know what the agent did, why it did it, or if they should believe it. Here’s how I design for trust.
Every executive asks: "Should we build our own AI or buy a tool?" The answer is almost always "it depends" — but here’s the decision matrix I use to give them a real answer in 30 minutes.
You can’t sell AI transformation with vibes. You need numbers. Here’s the ROI model template I use across every engagement — from time savings to revenue attribution to cost avoidance.
I write about AI strategy, product management, and transformation lessons — no fluff, no spam. One email when there's something worth reading.