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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Reputation Is a Lagging Indicator
Reputation is the last thing to arrive and the last thing to leave. The behaviors that build it precede it by years; the behaviors that destroy it precede the damage by years too. This lag is…
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The Long Game vs. the Quarter Game
Every senior revenue operator eventually has to choose, deal by deal, between the long game and the quarter game. The choice is rarely framed that starkly — usually it shows up as “push this deal now”…
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The First Board Deck on Revenue
Most first-time CEOs present revenue to their boards badly. Not because they’re hiding anything — because they haven’t been taught which numbers tell the real story and which numbers obscure it. The result is a board…
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Founder-Led Marketing: When to Hand Off and What to Keep
In the earliest stages of a company, marketing isn’t a function. It’s the founder. And most founders hand off marketing far too early, for the same reasons they hand off sales too early — fatigue, pride,…
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Strategic Alliances Are Mostly Theater
Most strategic alliances are theater. They produce press releases, executive photos, and quarterly progress slides, and they rarely produce revenue. Learning to tell the theater from the real thing is a skill, and the cost of…
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The Demand Gen Lie: Generation vs. Capture
Most of what companies call “demand generation” is actually demand capture. The distinction sounds semantic. It isn’t — it’s the difference between a marketing motion that drives growth and one that harvests existing interest from a…
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When to Walk Away From a Deal You’re Winning
Everyone talks about qualifying out early in the cycle. Few talk about walking away from a deal that’s actively winnable — one where the customer is engaged, the economics look plausible, and the close is in…
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The Forecast Lies
Most sales forecasts are fiction, and everyone senior enough to have seen three or four forecast cycles knows it. The question isn’t whether the forecast is accurate — it’s which kind of inaccurate, and what to…
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The Re-Engagement Motion: Why Closed-Lost Deals Are Still Alive
Every closed-lost deal is a future closed-won deal in disguise — if you know how to re-engage correctly. Most companies don’t. They close the deal as lost, the rep moves on, and the account goes silent…
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Outbound That Doesn’t Feel Like Outbound
The best outbound converts at multiples of the average outbound. The reason isn’t a better subject line or a cleaner cadence. It’s that the best outbound doesn’t feel like outbound. Average outbound feels like a template:…