The ultimate email writing tournament. Vote on 64 emails, head to head, until one wins the $1,000 prize Messaging Madness

YOUR 2026 MESSAGING MADNESS BRACKET

Start voting today on each match up, basing your choice on the email that makes you want to reply. Click "Start Voting" to get going.

MEET THE EMAILS

Get to know the entrants with our wall of emails — which will you choose?

Founder

YOU ARE

A software Founder of an AI CRM start-up with agentic sales support

TARGET COMPANIES

Nationwide telecommunications companies

TARGET RECIPIENT

Chief Sales Officer (CSO)

TARGET'S CHALLENGE

The CSO is under pressure to use AI to deflect calls (save money), but their chatbots are frustrating customers, causing Net Promoter Scores (NPS) to tank. They are at C3 looking for a solution that doesn’t feel robotic.

YOUR GOAL

To meet at C3, the Customer Contact Conference, to share your analysis.

YOU'RE OFFERING

A 30-minute conversation at C3 to share your analysis of the CSO's chatbot painpoints, offering a document that identifies the exact moment their current bot fails and frustrates users, and ways to fix it

EMAILS


Learn more about the madness

Bracketology

Messaging Madness isn’t just about signing up—it’s about earning your spot. Find out what that means and how we'll ensure one true champion emerges.

Learn the why behind the bracket

Cold email writing guide

Before you enter, take time to brush up your free throw and set yourself up for an alley-oop in the bracket with our tips on writing the perfect cold email.

Read our guide on copywriting

Terms and conditions

No competition would be a competition without terms and conditions. Make sure you read them before you put your name into the hat.

Read the terms and conditions