Stretch VP: Weekly

Stretch VP: Weekly

Progress = Happiness

What Saban, Wooden, Tony Robbins, and waterfalls can teach us about pipeline velocity and closing deals

Jun 17, 2026
∙ Paid

👋 Hey, I’m Grant. Each week I share lessons from the sales leadership trenches. What’s working, what’s not, and what I wish someone had told me years ago.

In this week’s Stretch VP: Weekly:

  • Why closed-won revenue is a lagging indicator of a broken system

  • The waterfall framework every founder needs before they hire their first rep

  • How to measure the activities that actually move the needle

Plus: The three coaches philosophies to help us rethink pipeline progress and winning

Want to work together? I help founders and revenue leaders build and operationalize the systems and structure behind predictable, scalable revenue. Reply to this email or DM me to explore what that could look like.

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The last few weeks have been a good reminder.

A bit light on the content lately. But I’ve been busy building out my fractional advisory work. But that also means I’ve been sitting across from a lot of founders and CEOs lately.

All different companies, all different markets, and all different sizes, but seemingly the same conversation.

Most of the time we end up talking about pipeline. How to build it. How to know if it’s actually healthy. How to tell if what they’re doing is working.

And most of the time, the place everyone starts measuring is the wrong end of the waterfall.


You’re measuring the output. Not the inputs.

Closed-won deals are the scoreboard.

Everyone looks at the scoreboard. I get it. It tells you if you’re winning or losing. It tells you if you can make payroll, hit the forecast, tell the board a good story.

Heck - its how sellers (and leaders) gauge success right?

But here’s the thing about scoreboards. They only tell you what already happened.

Nick Saban built seven national championships on one principle he called “The Process.” He said:

“Don’t think about winning the SEC Championship. Don’t think about the national championship. Think about what you needed to do in this drill, on this play, in this moment.”

I also shared one of my favorites from him last week that hits this home:

The score takes care of itself if you execute the right things in the right sequence.(another GOAT Coach - Bill Walsh wrote a book on this)

And most of the founders I’ve been sitting with lately? They’re staring at the scoreboard while the game is happening somewhere else.


What the waterfall actually looks like.

Let me walk you through how I’ve been talking about this with CEOs and founders.

We start at the bottom and build up. Stage by Stage conversion numbers.

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