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 Founder’s Bag: When the CEO Should Still Be Closing
At certain revenue stages, the CEO carrying the bag is the company’s single greatest growth lever. At other stages, it’s the single largest tax on the business. Knowing which is which is one of the hardest…
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Why Most Partnerships Fail at Month Four
The honeymoon ends at month three. Month four is when the work actually starts. Most partnerships never make it past that transition. I’ve seen this across every industry I’ve worked in — consulting, medtech, telecom, construction…
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Account-Based Everything (Not Just Marketing)
ABM — account-based marketing — was always supposed to be account-based revenue. The term got hijacked by marketing tech vendors, and now most organizations run ABM as a marketing program and wonder why it doesn’t deliver…
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Marketing Should Serve Sales, Not Measure Itself
Most marketing organizations have forgotten that their job is not to generate leads. It’s to create conditions where sales cycles are shorter, win rates are higher, and customers are better informed before they buy. Everything else…
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The Silent Second Stakeholder
The deal is closing. Your champion is thrilled. The forecast looks clean. Legal has the redlines. Your VP of Sales has already mentally booked the number. Then it doesn’t close. Every time I’ve seen this pattern…
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Multi-Threading or Mistake: The Single-Point-of-Failure Deal
Every single-threaded deal is one job change away from dead. That’s not hyperbole. That’s attrition math. The average senior B2B buyer stays in a specific role for 2-4 years. If your enterprise deal cycle is 6-12…
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Discovery Is Diagnosis, Not Interrogation
The best discovery call feels like a consultation. The worst feels like a deposition. If you leave discovery with a clean qualification grid and nothing else, you didn’t do discovery. You did intake. Real discovery is…
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The Champion Map: Who Actually Moves a Deal
Most enterprise reps think of “the champion” as a single person — usually the one who said “I love this” on the first call. That’s a dangerous simplification. Your champion isn’t one person. It’s a map…
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The Compound Interest of Trust
In every industry I’ve sold into — medical devices, management consulting, commercial construction, telecom infrastructure — the deals I won fastest were almost never the deals with the newest relationships. That’s not sentiment. That’s math. Trust…