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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Your First Sales Hire
Most founders hire their first salesperson too early, hire the wrong profile, and then blame the hire when it doesn’t work. The pattern is so consistent across the founders I’ve watched and advised that I now…
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Co-Selling Is a Contact Sport
“Let’s co-sell” is one of the most common and most meaningless phrases in partnership management. Everyone agrees. Nobody actually does it. The co-sell motion exists in press releases and dies in execution. The partnerships that actually…
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The Channel Partner Conflict: Why Most Channel Programs Die
Every company that sells through channel partners eventually runs into the same structural problem: direct sales and channel sales compete for the same deals. Managing that conflict poorly kills the channel motion. Managing it well turns…
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Narrative Architecture: Why Positioning Has to Live Everywhere
Most founders and CROs think positioning is a deck. It’s not. It’s the narrative architecture that shows up in every touchpoint — and the organizations that get this right have a coherence that compounds. The ones…
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The Pilot That Never Closes
The pilot sounds like progress. You’ve got signed paper. Users are in the system. The customer is engaged. Then the pilot ends, and the expansion to full deployment just… doesn’t happen. If you’ve sold enterprise anything,…
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The Mutual Close Plan
Most deals that slip in the final stages don’t slip because of product or price. They slip because the seller and the customer never aligned on what “closing” actually requires. The fix is a mutual close…
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Qualifying Out Is a Feature
The mark of a mature BD operator is not how many deals they pursue. It’s how many they correctly walk away from. Most sellers are trained to qualify in — find reasons to keep a deal…
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The Pre-Discovery Call: What to Do Before Your First Meeting
By the time you’re on a discovery call, a significant portion of the outcome has already been decided. Not by you. By how much you know walking in. The pre-discovery call is the work you do…
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Deposits Before Withdrawals: The Sequencing of Trust
Trust is an account. Most sellers overdraw it on the first touch and spend the rest of the relationship in repayment. The rule is simple and almost universally violated: deposits before withdrawals. Most sales training gets…
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The Relationship P&L
If relationships are a balance sheet asset — and they are, for anyone who sells — they deserve the same quarterly rigor as any other P&L line. Most operators don’t give them that rigor. Relationships get…