Bracketology: Finding the one in 64 for Messaging Madness

How can you chart a course to victory in Messaging Madness 2025? Here's what we're looking for in a "great cold" email.

March is all about brackets, and in Messaging Madness, the power of a cold email decides every matchup. But what makes one email better than another? How do we decide what deserves to advance? 

Like any good tournament, I’m here to share our Messaging Madness bracketology. Read on to learn about your path to victory - from landing on the final 64 entrants in Messaging Madness to helping the public vote over three weeks to crown our champion.

How are we choosing the final 64?

Messaging Madness takes 64 emails - 16 in four different scenario groupings - and puts them against each other to determine the champion. But, you need to be in the competition to win it.

We’re scoring the initial entrants transparently, giving you the information and guidance to write the best emails. Here’s what you need to know.

The Scenarios

We’ve created four different scenarios for you to choose from. Because outreach is about relevancy, it was necessary to give you specific details to keep your email focused. 

You are given information in each scenario that could and should be used in your email. Everything is relevant, whether it’s the name of the target recipient, their current solutions, or what you’re offering. 

Internally, we’ll assign a Hunter team member to each scenario based on their experience:

• Matt Tharp: Our CEO and long-time founder
• Ziemek Bucko: Our Senior Content Manager who knows cold email inside out
• Antonio Gabric: Our Outreach Manager who runs SEO outreach every day
• James Milsom: Our Head of Marketing who has managed multiple outreach teams

What makes a great, good, or bad cold email?

With the team set, it’s time to look at how we’ll review entries. We measure 5 factors:

1. Clarity and transparency: Does the recipient instantly know why they’re being contacted and what the sender wants?
2. Personalization: Is the email written for the recipient beyond their name and company?
3. Relevancy: Does the email present something valuable to the recipient based on their role and business needs?
4. Trustworthiness: Does the email use references (customers, competitors, social proof) to build credibility?
5. Readability – Is the email easy to scan, well-formatted, and free of unnecessary fluff?

We’ll score these factors on a scale of 1-3, with 3 being the highest score per factor. As we go through each, it becomes evident what a great, good, and bad email is.

Why did we land on these factors?

These factors come from our collective time in the outreach world, but are also informed by our State of Email Outreach 2025 research.

For instance, personalization is a factor because we found that 73% of decision-makers feel it is crucial to a good email.

Likewise, 71% of decision-makers named lack of relevancy as the primary reason they don't reply to an email.

And when it comes to trustworthiness, 36% of decision-makers need to feel that you're clear in your intentions.

How will these factors be scored?

To help you see how those factors will come to life, we've created the below.

You'll be rated 1-3 on each factor, with a max score of 15 overall. The emails with the highest ratings in each scenario will form the 16 per group and the final 64.

Great emails (3s across the board)

• The message is crystal clear from the first sentence.
• Personalization is sharp—showing real research and relevance.
• The offer directly aligns with the recipient’s pain points and role.
• The sender builds credibility by referencing companies or results.
• The structure makes reading effortless, with natural spacing and tight writing.

Good emails (Mostly 2s)

• The intent is somewhat clear, but some sentences could be sharper.
• Some level of personalization exists, but it could go deeper.
• The offer is relevant but may not be framed as compellingly.
• There’s an attempt to build trust, but it’s generic (e.g., “We work with companies like yours” instead of specifics).
• Readability is decent, but there’s room for improvement in formatting or conciseness.

Bad emails (1s across the board)

• It’s unclear what the sender wants.
• Personalization is nonexistent or purely token-based.
• The offer is irrelevant to the recipient’s role or business.
• There’s no credibility or proof.
• The email is dense, hard to read, or visually unappealing.

How we’re encouraging the public to vote

Public voting for the final 64 is simple: We’ll take it to LinkedIn and ask, "Which email would you respond to?"

Every round, your email will be placed against a competitor’s in our Bracket Hub. 

Anyone can vote on your email. The only guidance to voting is this: your gut. 

No complex scoring is needed. This is a gut check on which email works better. Our instinct often guides whether we enjoy or reject a cold email.

How can you win your round?

You made it to the final 64 because you earned it. Now, it’s time to promote it.

Want to make sure your email advances? Campaign. Share. Get loud.

• Post your email on LinkedIn using #MessagingMadness25 and ask your network to vote.
• On March 18, the Bracket Hub will be live. Point your audience to it: hunter.io/messaging-madness-bracket 
• Tell people why you deserve to win
• The more engagement you have, the better your chances are.

Messaging Madness isn’t just about great writing—it’s about getting buy-in. Because in cold outreach, the best email doesn’t always win. The email that gets attention and drives action does.

Does your email have what it takes? It's time to prove it.

Ready to enter?

Can your email go the distance? 

Make a copy of this document, choose your scenario, write your copy, and submit your entry via this form:

Hurry! You only have until March 13 to take your shot and re-write what a cold email should be.