RooktoRep

♖RooktoRep

Raw lessons from the front lines of tech sales -- from outbound, AI, & GTM functions.

1:1 Strategy Consult

Latest Articles

Outbound & GTM

AI + Leverage Systems

Break Into Tech Sales

Outbound & GTM

Steal My Cold Email Format

Oct 14, 2026

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4 min read

Steal My Cold Email Format

After 10,000+ cold emails, this is what works best for me.

Rook ♖
Rook ♖

Break Into Tech Sales

Building a Tech Sales Resume With Zero Experience

Oct 7, 2026

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4 min read

Building a Tech Sales Resume With Zero Experience

You probably have more relevant experience than you think...

Rook ♖
Rook ♖

Outbound & GTM

How to Build a Long Career in Sales

Sep 30, 2026

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2 min read

How to Build a Long Career in Sales

It's simple, but definitely not easy.

Rook ♖
Rook ♖

Outbound & GTM

Why Enterprise AEs Get Paid so Much

Sep 23, 2026

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3 min read

Why Enterprise AEs Get Paid so Much

There’s a lot more happening than just “selling software”.

Rook ♖
Rook ♖

Outbound & GTM

Metrics Aren’t for You

Sep 16, 2026

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2 min read

Metrics Aren’t for You

They’re for your champion selling the deal internally...

Rook ♖
Rook ♖

AI + Leverage Systems

AI Needs These 4 Things to Happen to Survive

Sep 2, 2026

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2 min read

AI Needs These 4 Things to Happen to Survive

This is starting to look less like an investment... and more like a parlay.

Rook ♖
Rook ♖
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♖RooktoRep

Raw lessons from the front lines of tech sales -- from outbound, AI, & GTM functions.

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