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Deal Strategy

Real deal stories from inside the hottest AI companies

The Raindrop that Evaporated by Choice

Aug 28, 2025

The Raindrop that Evaporated by Choice

Qualifying out after getting the "Yes"

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Windsurf Chaos & My 1st 7-Figure Deal

Aug 5, 2025

Windsurf Chaos & My 1st 7-Figure Deal

A tale a grit, teamwork, and creativity

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$150K to $1M ACV: The Constellation Strategy

May 22, 2025

$150K to $1M ACV: The Constellation Strategy

How to gracefully & rapidly expand deals across siloed orgs

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7-Figure W2s & The Golden Compass

May 15, 2025

7-Figure W2s & The Golden Compass

Building your Minimum Viable Org Chart (MVOC)

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3 Ways to Land In-Person Meetings

May 9, 2025

3 Ways to Land In-Person Meetings

Face-to-Face is Your Secret Weapon in the Digital Era

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7-Step Guide to Quarterbacking Product Builds as a Start-Up AE (Part 3 of 3)

Feb 25, 2025

7-Step Guide to Quarterbacking Product Builds as a Start-Up AE (Part 3 of 3)

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3 Ways Start-Up AEs Close Deals With an Incomplete Product (Part 2 of 3)

Feb 18, 2025

3 Ways Start-Up AEs Close Deals With an Incomplete Product (Part 2 of 3)

Qualification, BYO, and The Why Test

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Start-Up Sales: Feature Gap Framework (Part 1 of 3)

Feb 5, 2025

Start-Up Sales: Feature Gap Framework (Part 1 of 3)

This is Part 1 of a 3-Part Series focused on navigating product/feature gaps.

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The LEAP Method for PLG Sales

Jan 14, 2025

The LEAP Method for PLG Sales

Personally, I think selling a product with a strong self-serve / PLG motion is the easiest - but you need the right approach.

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Forget 20%, I want $1M in TIPS

Jan 7, 2025

Forget 20%, I want $1M in TIPS

In the world of startup sales, there’s no greater gift than a stellar customer reference...one that results in this:

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Gift of Giving: Tales of a Harley Davidson and Giant Rubber Duck

Dec 24, 2024

Gift of Giving: Tales of a Harley Davidson and Giant Rubber Duck

Gifts are not my love language.

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