I analyzed 730 display ads from Headway to identify at least three strategies that could help them double their creative velocity without sacrificing performance.

First, credit where it’s due: they’re doing a lot right.

Headway is testing aggressively. I was able to categorize their ads into 45 distinct angles. That’s genuinely impressive. Most companies struggle to find five to ten meaningful angles. Headway has 45, speaking to different audiences, pain points, and user contexts.

That level of testing is likely a big reason they’re one of the leading subscription products in the world today.

But here’s the issue:

The creative machine is optimized for algorithms.

I’m not convinced it’s optimized for humans.

If you read extensively, which I’d imagine overlaps heavily with their ideal target market — many of these ads feel slightly cringe. And that matters.

In this breakdown, I’ll walk through how they could:

• Convert more humans (not just feed algorithms)
• Expand their addressable audience
• At least double creative velocity

Let’s get into it.

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Roast #1: Format Fatigue

A lot of the ads look architecturally similar:

• Bullet points
• A stock image
• An exhortation about self-improvement

I understand why this works operationally. It’s modular. It scales. It’s easy to produce variations.

But it creates format fatigue.

When everything looks structurally the same, you miss entire pockets of attention.

There are formats that aren’t as easily scalable — but could unlock new audiences and incremental scale.

Here are three relatively low-hanging opportunities:

1. Wall-of-Text Ads

Messier. More human. Less templated.

These often feel more authentic and native.

2. Meme-Style Ads

Culturally fluent. Self-aware. Shareable.

3. iMessage-Style Conversations

These consistently perform well because they feel real. They feel like something someone would screenshot and send to a friend.

Visually, these formats are dramatically different from what Headway currently runs. They could simply reuse their existing high-performing messaging and port it into new structures.

That alone could unlock additional reach.

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Roast #2: It’s Not Written for Humans

Some of the messaging reads like this:

• “Stop rambling, lazy CEO.”
• “Don’t be a weak man.”
• “Real man. Become a legend.”

This sounds like a self-help guru shouting from a stage.

Ask yourself:

Would anyone screenshot this and send it to a friend?

Probably not.

It’s slightly embarrassing. Slightly cringey.

And that’s a problem.

There’s a massive opportunity here to humanize the messaging without sacrificing performance.

For example:

Instead of shouting transformation at the user, show a lived experience.

One of their high-performing headlines is:

“How I became the most interesting person in the room.”

That works because it taps into a real aspiration — social confidence, intellectual depth, curiosity.

Now imagine that framed as:

• An iMessage conversation
• A first-person story
• A relatable before-and-after

When you workshop real hopes, fears, and motivations — even with AI — you can reflect the actual lived experience of users.

That’s where performance and humanity meet.

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Roast #3: They’re Sitting on a Content Gold Mine (But Barely Show It)

This one genuinely surprised me.

Headway is a content product. It summarizes books.

Yet most ads barely show any real content.

Instead, we get bullet lists that look like:

• A syllabus
• A restaurant menu
• A generic checklist

You don’t feel the beauty of reading.

You don’t experience an insight.

You don’t taste the transformation.

They’re sitting on thousands of summarized books — each packed with compelling ideas.

That’s a gold mine.

Imagine ads that:

• Pull a powerful insight from a specific book
• Show a contrarian idea
• Tease a transformative framework
• Highlight a surprising stat or mental model

This could unlock thousands of new creatives almost instantly.

It would also tap into a slightly different audience:

People who genuinely love books.

People who enjoy reading.

People who just want to save time.

That’s incremental scale without abandoning the current engine.

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What Gets Them to the Next Level?

Through their current testing paradigm, Headway has climbed a big hill.

The next level likely comes from:

1. Expanding formats beyond modular bullet templates
2. Humanizing the tone of voice
3. Leveraging the depth of their actual book content

Each of these represents significant upside.

Not because what they’re doing is broken.

But because it’s incomplete.

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Want a Similar Breakdown for Your Brand?

If you’re curious what this kind of analysis would look like for your product, I’m happy to take a look.

You can reach out at rocketshiphq.com or drop a comment.

Always happy to roast, constructively.

See the full roast of Headway here: https://intelligentartifice.kit.com/cd7ce6006c