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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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.…
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The 2023-24 Efficiency Era
Looking back: April 2026 The period roughly from mid-2022 through most of 2024 was the efficiency era in B2B. Growth-at-all-costs became profitable-growth. Rule-of-40 became the standard benchmark. Revenue organizations had to re-optimize for capital efficiency in…
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Post-Pandemic Buyer Behavior
Looking back: April 2026 The buyer I sold to in 2019 doesn’t exist anymore. Some of what changed was temporary; some was permanent; some was always there and just became more visible. Sorting the three has…
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The Remote-Selling Shift
Looking back: April 2026 When enterprise selling moved remote in 2020, a lot of what had worked in the pre-2020 era had to be rebuilt. Some of the rebuilding produced better motions than existed before. Some…