• Generate 50+ headline ideas without hurting your brain
  • For conversion copywriters, product marketers, SaaS marketers
  • Headlines ready in less than 5 minutes!

You don’t have 3 hours to write headlines or crossheads.

“Spend 80% of your copywriting time on the headline,” you’re told. And for good reason. Headlines and crossheads on a website have a gargantuan job. (Hence this mastery program.) They have to:

  • Grab readers by the eyeballs <– ouch but yes
  • Make the visitor feel something
  • Sparkle with crystal-like clarity
  • Fit the messaging hierarchy down the page
  • Save the planet from being hit by an asteroid

That’s why when it comes to headlines and crossheads, not even the cleverest copywriter can hit the jackpot in a handful of tries. To get to the gold, copywriters work all the crappy headlines out of their system first. 

But if the CMO wants the wireframe by tomorrow, you just don’t have the luxury to become a headline hermit and hide in your copy cave. 

You have to strike gold—like, right now.

Here’s what to do: Get ChatGPT-4 to give you headlines so you have something to work with. The process goes like this:

  • Prompt ChatGPT-4 to generate 50–200 headlines in less than 5 minutes
  • Pick out the diamonds in the rough
  • Polish ’em up
  • Publish your conversion copy with a relaxed smile on your face, ’cause you didn’t even break a sweat 😏

The following is just one example of a product crosshead I wrote with the help of ChatGPT 4:

Web copy screenshot from Indy invoicing software website. Headline reads, "Break free from template hell"
Note: None of the website screenshots contain the product’s actual live copy. I used Chrome’s “Edit Anything” extension to change the copy displayed in my browser.

Step 1: To use ChatGPT to write headlines, start with a pain point

If your product cures a pain that users experience with competitors—Dawg, you gotta hit that!


Because pain points are great fodder for punchy headlines that resonate with your competitors’ dissatisfied customers. With pain points, you can use ChatGPT to write headlines galore!

Which means: Voice-of-customer research is key. It always was, always is, and always will be.

But if you’re in a bind and can’t spend hours researching, you can do some fast-and-furious review mining with ChatGPT in less than 30 minutes.

In fact, the two pain points I used for today’s exercise came from an AI-assisted pain-point analysis I wrote about here.

The two pain points we’ll focus on today are:

  • Steep learning curve/complexity of the software
  • Limited customization for invoices, proposals, and contracts

Step 2: Prompt ChatGPT to pump out headlines, ~50 at a time

If you used ChatGPT-4 to list out the pain points, you can continue prompting it for headlines in the same thread. 

Or you can start with a new thread—but be sure to give your bot enough context about your product, the competitor’s product, and the pain point you want to focus on. Like this:

Screenshot of ChatGPT-4 prompt

Copy-paste this prompt:

You are a conversion copywriter for a new [product or product category]. One of the unique value propositions of this new [product] is that it does not have the following pain point: [insert pain point]. 

Craft 50 product headlines that make this unique value proposition clear. Assume the reader has experienced this pain point with other products. Dig into that pain point by alluding to their past experience and promising a better experience with the new product. 

The headlines must talk to the reader directly using "You." Use emotion and empathy, and simple, direct language.

If you have specific phrases from your VoC research, you can add something this to the prompt, the way I did: 

Incorporate the words “newby” “intuitive” “overwhelming” and similar words.

ChatGPT will do its thing and dump a bit of a trash heap in front of you. But let’s be honest—so will any copywriter. 

The goal is to find a few diamonds in the rough and turn them into bling-bling copy for your website.

Here’s what I got:

Screenshot of ChatGPT-4 showing 50 headlines

Step 3: Decide which headlines have potential

Skim through the output. What stands out, and why?

This is where you have to think like a conversion copywriter. 

You’ll notice I highlighted a few phrases:

  • “Navigate like a pro”
  • “Clunky systems”
  • “Ditch the learning curve”
  • “You’re an expert from Day One”
  • “No newby feels left behind”
  • “Simplicity is our middle name. Feel the ease with every click.”

Here are some headline variations I came up with by stitching the above phrases together into headlines and subheads/body copy.

Webpage for Indy invoicing software, with headline modified to read: "So intuitive. Even if you're a newby." Subhead: "Ditch you clunky invoicing system. Send invoices like a pro from Day 1."
Webpage for Indy invoicing software, with headline modified to read: "No newbies get left behind." Subhead: "Ditch you clunky invoicing system. Send invoices like a pro from Day 1."
Webpage for Indy invoicing software, with headline modified to read: "You'll never feel like a newby." Subhead: "Ditch your complicated dashboard. Start invoicing like a pro from Day 1."
Webpage for Indy invoicing software, with headline modified to read: "Invoice your clients like a pro. From Day 1." Subhead reads: "No complicated dashboards here. Feel the ease with every click."

Step 4: Repeat the process for other pain points as needed

For my second pain point, I focused on lack of customization for invoices, contracts, and proposals.

Fill in the blanks of the prompt formula, like so:

Screenshot of ChatGPT prompt

Now, this time I was disappointed with ChatGPT’s output. And so I told my bot why I didn’t like the headlines it gave me, and I entered another prompt:

Screenshot of ChatGPT prompt asking it to iterate

These sound too fluffy and cheery, which makes them boring. Try sarcasm, humor, and more concrete language. Dig into the pain point of [add description] more by making the frustration palpable.

ChatGPT 4 came back with another 50. There were a few good ideas:

Screenshot of ChatGPT output, showing 25 headlines
Screenshot of ChatGPT output, showing 25 headlines

But I still felt like it could do better. As you can see, for some weird reason, every headline started with a yes/no question. And 99% of the time, yes/no-question-headlines (“Are you ready to X?”) are not effective because they can make your brand sound unsure of itself.

And so I told ChatGPT: 

Screenshot of ChatGPT prompt asking it to iterate

You're using too many questions. Try again without using yes/no questions in the headline.

I was able to get a few more ideas on the table. Check it out:

Screenshot of ChatGPT output, showing 20+ headlines
Screenshot of ChatGPT output, showing 20+ headlines

Here’s the copy using ChatGPT’s ideas:

Webpage for Indy invoicing software, with headline modified to read: "Stop sending proposals from the Design Dark Ages" Subhead: "Wow your client with fresh-looking proposals. 100% customized to your brand."
Webpage for Indy invoicing software, with headline modified to read: "Boring proposals be gone." Subhead: "Drag 'n' drop to your heart's content. Create 100% custom proposals with ease. Because it's 100% your brand."
Webpage for Indy invoicing software, with headline modified to read: "No more template torture." Subhead: "Create 100$ custom proposals and invoices. The easy way. Because it's your business and your brand."

And of course, for each headline that uses a phrase from ChatGPT, you can try lots of variations.

Let’s say I want to play around with the “Design Dark Ages” theme, I could write:

A: Proposals that aren’t stuck in the Design Dark Ages

B: Your proposals don’t have to look like they’re from the Design Dark Ages

D: Set your proposals free from the Design Dark Ages

Basically, each solid idea you get from ChatGPT will instantly give you 5–10 more variations.

And that’s one of the awesome advantages of AI. If you hit a dead end, you can dust yourself off and try again. Work your angles. It takes less than a minute to rework your prompt and get another bucket of headlines.

Plus, when you see bad headlines, often this “anti-inspiration” lights a fire under your butt to create something way better. It’s just lube to your writerly gears.

I tried this AI prompt on my favorite vegan chocolate bar brand. Here’s what happened.

I wanted to test this prompt in a completely unrelated industry and product: Vego, a vegan chocolate company that has blown me away with vegan chocolate that:

  • actually tastes delicious
  • melts in your mouth
  • is seriously reminiscent of classic Swiss or Belgian milk chocolate

As someone who’s tried every vegan mylk chocolate bar on the planet, I’ve tasted my fair share of duds. I’m familiar with the pain point of biting into a brick that is too sweet, somewhat flavorless, and not nearly creamy enough.

Ever since Vego entered the market, I’ve been obsessed.

For fun, I decided to use my pain-point headline prompt to create better crossheads for their product website.

But first, take a look at the original:

Vego chocolate bar page with original crosshead that reads: The ultimate classic vegan chocolate bar! Just divine!

As a happy customer, I can tell you this crosshead doesn’t do Vego justice.

Here’s the ChatGPT prompt, adapted to the product and pain points:

ChatGPT prompt modified to suit vegan chocolate bar product

Here are the 50 headlines from ChatGPT:

Screenshot of ChatGPT showing 25 headlines about vegan chocolate bar
Screenshot of ChatGPT showing 25 headlines about vegan chocolate bar

Combining some of the highlighted ideas, I came up with the following crossheads and body copy:

Key tips and takeaways

  • Always remember to give ChatGPT context. You’d do the same for a junior copywriter. You can use my review-mining hack as context, or you can just tell ChatGPT, using clear, concrete, concise language.
  • Even bots can get stuck in a rut. Like the way ChatGPT decided, randomly, to start each headline with a yes/no question. When that happens, tell ChatGPT why those headlines are no good and ask it to recast them. Just be specific when you re-prompt. Experimentation is your friend.
  • At some point, your bot may start to sound like it’s had too many beers. Mixed metaphors. Incoherent lines. Buzzword bingo. If you notice your outputs are starting to degrade, just wipe the slate by starting a new thread. I’ve noticed I’ll get a variety of outputs on the exact same prompt just by starting a new thread. And last time I checked, having an extra 50, 100, or 150 headlines to work with isn’t a bad thing!
  • Keep your headline batch size to about 50. I’ve found that 50 headlines at a time gives you a good sampling. A bucket of 20 doesn’t give you enough to rummage through, while a bucket of 100 gives you too much of the same junk.
  • Don’t overprompt ChatGPT until you get a perfect headline. You’re better off taking bits and pieces of what it generates and turning it into a finished headline or crosshead.

Use cases

  • Write compelling headlines for comparison pages
  • Write product headlines showing how your features make customers’ lives easier
  • Stack your product’s unique selling points against competitor pain points
  • Write seal-the-deal headlines to convert visitors who are thinking of switching vendors
  • Create product headlines to test in a campaign or on a message-testing site like Wynter.

Get the scoop on what makes for a scroll-stopping headline

To learn more about the anatomy of a great headline, go here, here and here.

Happy prompting and writing!