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 Conference Dinner Playbook
Some of the highest-ROI BD activity of any conference is the dinner. Not the sponsored dinner — the ones you organize yourself. Done well, a 10-person dinner at a good restaurant during a major conference is…
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Why Your Deal Died in Procurement
“We’ve hit a snag in procurement” is one of the most common phrases a seller hears late in a deal cycle. By the time it’s said, the deal is usually already in trouble, and the trouble…
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The Quiet Year: Why Relationship Investment Looks Unproductive in Year One
If you start seriously investing in your network today — more intentional introductions, more consistent cadence, more generous presence — you probably won’t see measurable returns for a year or more. This disconnect between input and…
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The Content That Actually Converts
Most B2B content is produced by committee, optimized for SEO or social engagement, and converts at rates close to zero. The content that actually drives pipeline is typically produced by a small number of people, optimized…
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Co-Marketing Without Co-Selling
Many partnerships are called “partnerships” but are really co-marketing arrangements. Press releases, joint webinars, logo exchange, shared content — these are marketing collaborations that don’t require the operational complexity of true co-selling. Recognizing this distinction —…
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When to Say No to a Round
Most founder advice is about how to raise money. Less discussed is when to decline it — which, for certain founders at certain stages, is one of the most consequential decisions they’ll make. I’ve watched founders…
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The Three Calls That Matter in a Deal
Every enterprise deal I’ve seen close had three specific calls that disproportionately determined the outcome. Not the first call, not the demo, not the closing call — those matter, but they’re not the ones that decide.…
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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…