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

The Art of the Calendar Invite

May 27, 2026

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4 min read

The Art of the Calendar Invite

Managing momentum before the meeting even starts

Rook ♖
Rook ♖

AI + Leverage Systems

The Outbound System I Built In Claude

May 20, 2026

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6 min read

The Outbound System I Built In Claude

My exact workflow + prompt behind my outbound.

Rook ♖
Rook ♖

Outbound & GTM

What Your Cold Emails Are Competing Against

May 13, 2026

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3 min read

What Your Cold Emails Are Competing Against

I sat next to a CFO on a flight recently... this is what I learned.

Rook ♖
Rook ♖

Break Into Tech Sales

Messaging That Gets You Referral Calls

May 6, 2026

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2 min read

Messaging That Gets You Referral Calls

Real examples on how I messaged my way into interviews.

Rook ♖
Rook ♖

Outbound & GTM

Objection Handling 101

Apr 29, 2026

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3 min read

Objection Handling 101

5 objections I hear every week (and what actually works)

Rook ♖
Rook ♖

Break Into Tech Sales

Rook’s Guide to Break Into Tech Sales #2: Anthropic

Apr 22, 2026

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3 min read

Rook’s Guide to Break Into Tech Sales #2: Anthropic

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

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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