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IN THIS EDITION

Something quirky about the edition

  • Article: Upside won’t close deals, but playing into these two emotions will

  • How sellers are winning when “outreach is dead”

  • 11 Claude prompts to land more interviews

  • And more…

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SELLER’S SECRETS

Upside won’t close deals, but playing into these two emotions will

There's an idea floating around right now that's worth sitting with: every business case, at the end of the day, is built on fear or greed. That's it. Two levers.

"Increase revenue" isn't a motivator. Nobody wakes up moved by a bigger number on a slide deck. What actually moves people is what increased revenue does for them personally.

Increase revenue so the exit multiple jumps and the payout is life-changing. Greed.

Increase revenue so they don't get fired in the next round of cuts. Fear.

Increase revenue so they finally get the promotion they've been circling for two years. Greed again.

Strip the corporate language off any "business case" and you'll find one of these two underneath. Always.

Most sales reps miss this part

Here's where it gets useful. The fear or greed driving your champion isn’t always the same fear or greed driving the person who actually signs.

Your project lead might be motivated by looking good in front of leadership. That's their fear-greed cocktail. Promotion, visibility, not getting blamed if the project flops.

But the VP of Engineering above them? Different game. They might care about headcount protection, shipping velocity, or not being the bottleneck on a board-level initiative.

The CFO above them? Different again. Margin. Cash. The number they have to defend on the next earnings call or to the PE firm that owns the company.

Three people. Three completely different fear-greed profiles. And most reps are out here pitching the same generic "ROI story" to all three.

What this changes about how you sell

If you accept the premise, a few things start to look obvious:

Discovery isn't about uncovering pain in the abstract. It's about figuring out what each person stands to personally lose or personally gain. Those are different questions, and they require different conversations.

Multi-threading isn't a tactic to look thorough. It's the only way to actually map the fear-greed terrain across a buying committee, because the terrain changes at every level.

And the business case you build with your champion? It's a starter kit. It works for them. It almost certainly does not work for the CFO without a real translation layer, because the CFO isn't afraid of the same things and isn't greedy for the same things.

The quiet implication

Most "stalled deals" aren't stalled because the product is wrong or the price is too high. They're stalled because somewhere up the chain, there's a person whose personal fear or personal greed isn't being spoken to, and that person is the one with the actual veto.

If you can't articulate, for every key player in a deal, what they're personally afraid of and what they're personally hungry for, you don't have a deal. You have a hopeful conversation with one person who likes you.

Fear or greed. Pick the right one for the right person. That's the work.

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