Oliver Buchannon
Rook ♖

Raw lessons from the front lines of tech sales -- from outbound, AI, GTM, and what actually works.

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 ♖

Outbound & GTM

+1

5 CRM Reports to Generate Pipeline

Apr 15, 2026

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2 min read

5 CRM Reports to Generate Pipeline

Start here before going net-new.

Rook ♖
Rook ♖

Break Into Tech Sales

Why You’re Not Getting SDR Interviews

Apr 8, 2026

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6 min read

Why You’re Not Getting SDR Interviews

Even If You’re Qualified...

Rook ♖
Rook ♖

Outbound & GTM

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 ♖

Outbound & GTM

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 ♖

Outbound & GTM

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 ♖

Break Into Tech Sales

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 ♖

Outbound & GTM

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 ♖

Break Into Tech Sales

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 ♖

Outbound & GTM

+1

The Future of GTM Orgs

Feb 18, 2026

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6 min read

The Future of GTM Orgs

Why sales teams will look radically different by the end of 2026.

Rook ♖
Rook ♖

Break Into Tech Sales

Spotting the Correct Sales Org

Feb 11, 2026

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3 min read

Spotting the Correct Sales Org

Your first sales org can dictate your entire career timeline. Here is how I go about finding orgs that are worth your time.

Rook ♖
Rook ♖

Outbound & GTM

7 Quick Tips to Improve your Cold Email Game

Feb 4, 2026

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3 min read

7 Quick Tips to Improve your Cold Email Game

I've written 10,000+ cold emails... here's how to get more responses

Rook ♖
Rook ♖

Outbound & GTM

The Easiest Warm Leads You’re Overlooking

Feb 1, 2026

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2 min read

The Easiest Warm Leads You’re Overlooking

Try out this simple tip to find leads that are hiding in plain sight

Rook ♖
Rook ♖
Welcome to ♖RooktoRep

Feb 1, 2026

•

3 min read

Welcome to ♖RooktoRep

Who I am. My story. Why you should continue following along.

Rook ♖
Rook ♖

♖RooktoRep

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

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