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

Follow-Up With a Purpose

Aug 5, 2026

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3 min read

Follow-Up With a Purpose

Why the best sales reps don't "just check in".

Rook ♖
Rook ♖

AI + Leverage Systems

AI Usage v.s. Quota Attainment

Jul 29, 2026

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2 min read

AI Usage v.s. Quota Attainment

And the not-so-surprising correlation between the two...

Rook ♖
Rook ♖

Break Into Tech Sales

I Recently Interviewed 3 SDR Candidates

Jul 22, 2026

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2 min read

I Recently Interviewed 3 SDR Candidates

Two moved on. One didn't. Here's why...

Rook ♖
Rook ♖

Outbound & GTM

+1

The Open-Source Business Model

Jul 15, 2026

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4 min read

The Open-Source Business Model

And why I'm so bullish on it for sales reps...

Rook ♖
Rook ♖

Break Into Tech Sales

How to Evaluate Sales Orgs

Jul 8, 2026

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4 min read

How to Evaluate Sales Orgs

Before you accept the offer, read this...

Rook ♖
Rook ♖

Outbound & GTM

The 80/20 Rule of Sales

Jul 1, 2026

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2 min read

The 80/20 Rule of Sales

Revenue vs Non-Revenue Generating Tasks...

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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