RooktoRep

♖RooktoRep

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

Latest Articles

Why Most Outbound Is Failing Right Now

Apr 1, 2026

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8 min read

Why Most Outbound Is Failing Right Now

And how volume and personalization isn't the answer

Rook ♖
Rook ♖
The Importance of Email in Outbound Sales

Mar 25, 2026

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4 min read

The Importance of Email in Outbound Sales

Not because it’s perfect... but because it does something other channels can’t.

Rook ♖
Rook ♖
This Will Separate Top Reps in 2026+

Mar 18, 2026

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4 min read

This Will Separate Top Reps in 2026+

Nope, its not about AI... but it is something that we've gotten away from.

Rook ♖
Rook ♖
Rook’s Guide to Break Into Tech Sales #1: Vercel

Mar 11, 2026

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6 min read

Rook’s Guide to Break Into Tech Sales #1: Vercel

Ongoing series of how I'd break into different tech sales organizations.

Rook ♖
Rook ♖
How to Bring Ghosted Conversations Back to Life

Mar 4, 2026

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4 min read

How to Bring Ghosted Conversations Back to Life

Prospects go silent. It's part of being in sales. Here is how to get the convo rolling again.

Rook ♖
Rook ♖
The Tech Sales Interview Process

Feb 25, 2026

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3 min read

The Tech Sales Interview Process

Trying to break in? This is what's ahead.

Rook ♖
Rook ♖
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♖RooktoRep

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

© 2026 ♖RooktoRep.
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