Word From Between the Cans

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August 11 2026 Jay Feitlinger

How to Build Buyer Trust When Everything Looks Like AI

Your pipeline looked healthy in January, and now deals are stalling for reasons nobody can name. I've had a run of conversations this year with clients and prospects who describe the same pattern, and the finger-pointing starts within about a ...

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August 10 2026 Jay Feitlinger

Slow Season or Broken Cadence? How to Tell the Difference Before Q4 Planning

Every August, somebody on the leadership team says the same thing. "Q3's always slow for us." Pipeline reviews get shorter, the forecast softens a little, and everyone nods as the calendar explains it. The conversation moves straight to Q4 planning ...

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August 6 2026 Jay Feitlinger

How Much Free Work Should You Do Before a Contract?

You spent six weeks scoping a deal before anybody signed anything, and now your operations lead is looking at the internal budget sheet like you personally lit it on fire. Sarah Shepard, our COO and my co-host, and I have been having some version of ...

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August 3 2026 Jay Feitlinger

Closed Deals Still Leak Revenue After the Contract Is Signed

Winning the deal isn't the finish line. Here's what breaks down in the handoff from sales to delivery, and why it quietly costs B2B companies expansion revenue.

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July 31 2026 Sarah Shepard

I Ran a Risk Experiment, and All I Got Was a Terrible Haircut (What Three Failed Tests Taught Me About Risk)

There's a whole genre of TV where people buy a house somewhere with better weather than wherever they came from, and I was on the couch watching one of those when a couple from New Jersey explained how they'd ended up in St. Thomas. They told it the ...

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