Messaging Madness 2026: Cold Email Is Out, Outreach Is In

It’s back.

Last year, we launched an experiment. 

We wanted to see what happened when we pitted the best cold email writers against each other in a bracket-style tournament. 

The result? Messaging Madness.

We saw thousands of votes and one undeniable truth: the "spray and pray" era is long-gone.

Welcome to Messaging Madness 2026. 

This year, the scenarios are tougher, and the philosophy has changed. 

Let’s walk you through the competition where you can win $1,000 for writing one outreach email and how to enter.

What is Messaging Madness?

Messaging Madness is an email-writing competition where 64 competitors are split into four scenarios. The goal is to write an outreach email based on one scenario. 

From there, the public votes on the emails that they’re most likely to reply to. Each round features a one-on-one matchup in which one entrant moves forward, and the other is eliminated based on the votes they receive. 

The rounds are fast. The votes matter. And entrants can promote their emails however they see fit. Those who make the last four will receive a year of Hunter’s Starter plan.

Win, and you’ll earn $1,000!

Lead gen doesn’t need to be cold

In 2025, we called this a "cold email" competition. But looking back at the winning entries, we realized something important: None of them felt cold.

When you truly research your prospect, understand their specific pain points, and segment your list so effectively that your message lands at the exact right moment - that’s not a "cold email." That’s outreach.

Cold implies you are a stranger intruding on their day. Outreach implies you are a peer offering a solution they’ve been waiting for.

That is the theme of Messaging Madness 2026. 

We aren’t just looking for clever subject lines; we are looking for the vital connection between your recipient’s pains and what you can do to help them turn a cold lead into a warm conversation.

A look back at the Madness of 2025

For those who missed it, last year was a whirlwind. 

We reviewed hundreds of entries, narrowed them down to a final 64, and let the public vote.

We learned some incredible lessons from the 2025 bracket:

• Relevance reigns supreme: The most "clever" emails often lose to the most relevant ones.
• Length is a myth: We saw 200-word emails beat 50-word emails because the longer email actually said something of value.
• The "Human" element: The winners didn't sound like AI templates. They sounded like humans writing to humans.

Why this competition exists

We run Messaging Madness to prove a point: Writing a great email is only half the battle.

You can write the most poetic prose in the world, but if you send it to the wrong person, it’s spam. Conversely, you can find the perfect lead, but if your message is generic, you’ll be ignored.

To win in 2026, you need to master both:

1. Segmentation: Knowing exactly who you are targeting and why.
2. Messaging: Articulating value that resonates with that specific segment.

The rules and timeline

This is a bracket-style tournament. Entering is simple, but writing the winning email is anything but easy.

1. Choose your scenario: Pick one of the four scenarios below.
2. Write your outreach: Write the perfect initial email based on the prompt.
3. The selection: Our internal judges will select the top 16 entries for each scenario (64 total) to enter the bracket.
4. The vote: The public will vote on head-to-head matchups on the Hunter bracket until a champion is crowned.

📅 Entry deadline: March 10

📢 Bracket announcement: March 16

1️⃣ First round voting: March 17-18

2️⃣ Second round voting: March 19-23

🏀 Super 16 voting: March 24-25

📖 Open-rate 8 voting: March 27-30

🔥 Follow-up 4 voting: March 31-April 3

🏆 Championship voting: April 6-7

The 2026 scenarios

Each scenario is owned by a member of the Hunter team, who will act as the "Commissioner" for that bracket. These scenarios give you all you need to write the best email possible.

Scenario 1: The Founder

Judge: James Milsom, Head of Marketing, Hunter

• You are: A software Founder of an AI CRM start-up with agentic sales support.
• Your target: Chief Sales Officer (CSO) at a nationwide telecommunications company.
• The challenge: The CSO is under pressure to cut costs using AI, but their current chatbots are frustrating customers and tanking Net Promoter Scores (NPS). They are C-Suite level, looking for a solution that doesn't feel robotic.
• Your goal: Secure a meeting at C3 (the Customer Contact Conference) to share your analysis.
• Your offer: A 30-minute conversation at C3 to share a document identifying the exact moment their current bot fails, along with a fix.

Scenario 2: The Content Manager

Judge: Ziemek Bucko, Senior Content Manager, Hunter

• You are: A Content Manager at a manufacturing firm.
• Your target: Communications Directors at podcasts like Problem Solved, Well There’s Your Problem, and Manufacturing Happy Hour.
• The challenge: These podcasts are bombarded by guests. You need to stand out and make it a "no-brainer" for them to feature your Director of Engineering.
• Your goal: Book your Director of Engineering on the show to build relationships and support link building.
• Your offer: You will provide high-res schematics, a 'virtual tour' video of your factory floor, and a technical case study PDF for their show notes.

Scenario 3: The CEO

Judge: Matt Tharp, CEO, Hunter

• You are: CEO of a recruitment company.
• Your target: Managing Partners in Commercial Real Estate (CRE).
• The challenge: Top producers are leaving for competitors with aggressive offers. These Partners lack transparency on market rates and don't know how to stop the bleed.
• Your goal: Get them to contribute to your report: “The Future of [City] Real Estate: 2026 Leadership Predictions.”
• Your offer: A 30-minute interview that allows the Partner to showcase why their firm is different to potential recruits (while seeing how other firms attract talent).

Scenario 4: The Account Executive

Judge: Antonio Gabric, Outreach Manager, Hunter

• You are: An Account Executive at a global research and advisory firm.
• Your target: Chief Supply Chain Officers (CSCO) in Life Sciences.
• The challenge: The CSCO is being asked by finance to spend less, but they need to spend more to build supply chain resilience. They are stuck in a "cost vs. resilience" paradox.
• Your goal: Demonstrate value through exclusive data.
• Your offer: Exclusive access to peer benchmarks & risk toolkits showing how competitors are investing in supply chains and which AI technologies actually help rather than adding cost.

How can you enter Messaging Madness 2026?

Do you have the skills to turn a cold lead into a warm opportunity?

Select your scenario, sharpen your copy, and submit your entry via the form below before the buzzer sounds for entries on March 10.