Notes on technology, leadership, and decision-making inside complex organizations. I write about the choices that actually matter — not just the tools or the trends, but the judgment calls that determine whether something ships or stalls.
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Why Most Demo Calls Are Broken
Most software and technology demos are designed to show off the product. The buyer’s perspective — what they actually need to understand, what decisions they’re trying to make, what risks they’re trying to assess — is…
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The Cadence of Showing Up
The relationships that compound are the ones where you show up consistently, not the ones where you show up intensely. This is obvious stated that way, and harder to implement than it sounds, because intensity is…
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The Founder’s Customer Advisory Board
A Customer Advisory Board, done well, is one of the highest-leverage activities a founder can run in the early and growth stages of a company. Done poorly, it’s a quarterly meeting that makes executives feel important…
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The Hire I Got Right (and Why)
Looking back: April 2026 I’ve made a lot of hires in my career. I’ve gotten many of them wrong. I’ve gotten a few spectacularly right. The one I think about most isn’t the most senior hire…
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The Board Meeting That Changed How I Forecast
Looking back: April 2026 There was a specific board meeting, years ago, that changed how I thought about forecasting. I hadn’t realized until that meeting how deeply I’d absorbed a culture where forecast commitment was treated…
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A Partnership That Taught Me to Write Kill Criteria
Looking back: April 2026 There’s a specific partnership in my past that I think about more than most. It’s the partnership that made me a believer in kill criteria — the written, specific, measurable conditions under…
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The Day I Realized the Channel Was Broken
Looking back: April 2026 I’ve been through multiple channel partnerships over the course of my career — both as a vendor managing a channel and as an observer of companies that did. The moment I most…
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The First Time I Fired a Customer
Looking back: April 2026 The first time I formally ended a customer relationship was harder than I expected and more important than I realized. It’s one of those small professional moments that shaped everything that came…
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Crossing From Employee to Founder
Looking back: April 2026 The transition from employee to founder is one of the most discussed, most written-about, and most mischaracterized transitions in professional life. Everyone talks about the obvious changes — autonomy, risk, ownership. The…
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What the AI-Era Buyer Looks Like
Looking back: April 2026 The buyer I sell to in 2026 is materially different from the buyer of 2022. Some of the changes are obvious — AI-assisted evaluation, faster information synthesis, different expectations about vendor responsiveness.…