The throughline across all of it is operating reality. Governance only matters if it changes decisions. Strategy only matters if it survives execution.
Occasional notes on AI governance, operating model design, product leadership, and what boards keep missing.
When Microsoft licensing shifted to monthly SaaS, our revenue line fell off a cliff. We rebuilt a $1.2B business by redesigning how we attached services to software. The same structural break is happening again as AI compresses SaaS economics.
A first-hand account of leading CDW's Microsoft productivity business through the shift from enterprise licensing to monthly SaaS, inventing a services-led MSP model — and the parallels to today's 'SaaS apocalypse' as AI reshapes software economics.
Read the article →Start with the most recent articles, then use the archive or search page to move by topic and operating question.
Browse the archive →Most AI board reports describe enthusiasm and pilots. This template forces management to show how AI labor is changing operating metrics, who owns the outcomes, and what decisions the board now needs to make.
Read →The smartest AI diligence questions aren't about the model. They're about whether the portfolio company can absorb AI as labor, govern it, and tie it to accountable operating results on the clock that matters.
Read →If AI is delegated labor, the org chart has to show where that labor sits, who supervises it, and how managers are held accountable for blended output. Most companies aren't even drawing that picture yet.
Read →The trust tier model lets AI governance scale with real-world consequence, so low-risk digital labor moves fast while high-risk systems get the control they deserve.
Read →The documentation and controls required for AI diligence are built over time. If AI is part of your value story, starting when the banker calls is already late.
Read →Non-linear careers look messy from the inside and obvious in hindsight. The operating advantage is the pattern recognition they create across systems, not the novelty of the path itself.
Read →The frameworks in these books are the foundation of the advisory work. If you want depth, start here.
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