How I Wrote a Story-Based Sales Email That Landed Me in the Top 5 in a Copywriting Contest

Photo by Hello I’m Nik 🇬🇧 on Unsplash

I came in 4^th place, to be exact. Now, that might not seem like much, but there were roughly 78 entries from copywriters who ran the gamut from fairly new to quite successful and experienced.

I’ve been doing this here copywriting and marketing thing since about 2001, but some of my fellow copywriters participating in this? Let’s just say I was a little (and by little, I mean a lot) intimidated.

In fact, initially I thought, “No way am I entering a contest I likely won’t do well in given the competition, especially since it’ll take me hours to write an entry. I’m already at capacity with work right now.”

[Can ya hear all the limiting beliefs nonsense going on there? Yikes!]

But deep down, I really wanted to do this. Because if you’re not making yourself uncomfortable from time to time, you’re not growing. So say the personal development geeks. Of which I am one. 😊

I’m sharing the contest details and my entry here, because if you pay close attention to the rules, template, questions, and other guidance Kevin and Chris presented, along the prep work I did before submitting my entry, you’re sure to learn a thing or two about what it takes to write a story-based email that sells.

The Background

The contest took place inside the Copy Chief community, which I’m a proud member of.

The emails were judged by Kevin Rogers, founder of Copy Chief and expert direct response copywriter who has helped clients earn $100M in sales, and fellow Copy Chief member Chris Orzechowski, email copywriter & consultant extraordinaire who helps e-commerce companies earn big paydays with email.

Kevin and Chris critiqued the email entries via video inside Copy Chief, and chose the top 5; we lucky 5 received a coveted Copy Chief “Nobody Writes Alone” t-shirt. Yee-haw! The grand prize winner also won a scholarship to Chris’s Email Copy Academy and an email sequence review.

The Challenge: Write a “story-based” email that sells

The fellas did a fantastic presentation explaining the elements of, and psychology behind, storytelling emails that sell to help us prepare for the challenge.

The Rules

We were given three products to choose from to write the sales email for:

A pillow, a pressure washing service, or a productivity course.

We were to pick the product, write a story-based email that sells people on buying the product, then post our entry inside the Copy Chief forum.

I chose the pillow, and used Casper for my model. But I renamed my “imaginary” product the Euphoria Pillow. 😊

We were graded on:

• Subject line
• Strength of the story/hook
• Clarity & readability
• Call to action language

Emails That Sell Need to Do a Few Important Things

In order to write a persuasive email that moves people to action, we had to do three things: determine what our ideal customer’s current beliefs were, tell stories to implant new beliefs that would get them interested in our chosen product, and give them an action to take that would bring them closer to their goal, such as making a purchase.

To determine what to say, we were instructed to:

1. Talk to people in our market – I did this by chatting with couple of friends who had sleep issues and had recently purchased pillows. I also did lots of review mining: I sifted through pillow reviews on the Casper website, plus positive and negative reviews of other premium pillows on Amazon. I saved loads of this voice of customer data into a doc to use while writing my sales email. (You need to understand where people are now, the challenges and struggles they’re facing, and where they want to ultimately be – which is what your product or solution offers. You can’t write persuasive copy without research and voice of customer data. Full stop)
2. List out their problems – The review mining mentioned above gave me lots of intel about problems and challenges. For example, many people suffer poor sleep and wake up with a stiff neck and other aches and pains because they don’t have a quality pillow. And we all know poor sleep has a hugely negative impact on everything else we do in our day-to-day lives.
3. List the outcomes (results) they want in their life – On the surface they just want to wake up pain-free. But what they really want is to wake up feeling refreshed, well-rested, and ready to tackle the day. To slay the day. To handle everything with grace, ease and joy, the way you do when you’ve gotten eight glorious hours of deep, uninterrupted sleep.
4. List their “false beliefs” – Some could include: “Spending $80 on a pillow is crazy, it’s not worth it.” “A premium pillow isn’t going to make that much difference in my sleep quality.”
5. List “new beliefs” they need to gain in order to make a buying decision – “$80 is a small price to pay for something that can seriously improve your sleep, and because quality sleep is so important to health and overall happiness, it’s worth every penny.”

The Template

Chris shared a basic outline of emails that sell:

1. Subject line
2. Story
3. Segue/The ‘Turn’
4. CTA

(Optional): P.S.

(You’ll see these things in action in my email entry, below)

He also talked about eight kinds of subject lines, along with eight different story frameworks.  I chose the personal story framework for my email.

And of course, we covered the uber-important call to action: you must tell people what to do, why they need to do it, and why they need to do it now.

BUT … even after all this, we’re still not quuuuite ready to begin writing.

Nope, first, we needed to answer the following questions. My answers included here:

1. Where does this email fit into the context of the marketing funnel?

It comes after web visitors have read some info on the Casper website, or have otherwise been exposed to the brand, and they’ve signed up for the Casper email list to learn more.

2. What is the objective of this email?

To make a sale

3. What’s the new belief you want readers to have?

That an $80 pillow is totally worth it and can change their life

4. What’s a story/hook that can implant that belief into their brain?

Talk about how quality sleep is the most important health action they can take, as illustrated through a personal story about the before-and-after results of getting quality sleep; demonstrate through a story that shows – not tells – the transformation. Could also consider using data on sleep; benefits of quality sleep, etc.

5. What is your call to action going to be?

Buy now

6. What ‘reasons to act now’ do we need to add?

Don’t miss one more night of quality sleep and go through your days unable to do all you want to do, to the best of your ability. Life is too short, and you have too much you want to do, for that.

The presentation Chris and Kevin gave was so good, and so thorough, it’s not possible to share all of it here, but I’ve outlined the very basics above.

Prep I Did Before Writing

Once I decided to enter the contest, I was all in. Meaning, I did what I do with every actual client copy project I take on – research, research, and more research, which comes in a few varieties:

:: I talked to a couple of friends with sleep issues. I asked how the sleep issues presented, and what they did to resolve them.

:: I signed up Casper’s email list to see how they do email.

:: I spend loads of time on the Casper website, reading about their pillows (product research), AND, more importantly, reading customer reviews (to gather voice of customer data).

:: I did review mining of other premium pillows on Amazon to gather more voice of customer data on things like: where people are in their solution-seeking journey when they arrive at the place of deciding to spend upwards of $80 for a single pillow, what problems they’re trying to solve, what they’ve tried before that didn’t work, and to suss out the transformation they really want. Sure, they want a good night’s sleep, but more than that, they want all the benefits that derive from a good night’s sleep.

:: If this were a real project with a real client, I also would have: had the client fill out my intake questionnaire, had a call to review completed questionnaire and discuss the direction and goals of the copy, talked to a handful of actual customers, done loads more product research, and undertaken more competitor analysis.

My Sales Email Entry

(Chris and Kevin’s feedback is pasted in at the end of the email.)

Original email subject line ideas:

Red wine, tough love, and clouds made of rainbows

Alternative SLs:

Pairs nicely with success

$80 for a pillow?!?! You’re crazy.

A handful of other subject lines I considered, but didn’t post as part of my entry:

BOOM! This is how you improve every area of your life … for just $80

There’s not an app for that

As soon as I laid down, I was in love

This 5-letter word changed EVERYTHING

Why aren’t more people talking about this?

Is this the missing link to a better life?

You can’t put a price on this

__ % of adults don’t get enough of this

Pillow talk

Driving drunk or driving underslept … which is more dangerous?

Sixty percent of adults have done this life-threatening thing

EMAIL BODY COPY

One Saturday night a few weeks ago, Ronda, my BFF of 30+ years, committed one of the kindest acts a trusted friend can ever do.

She called me out on my bullshit.

Over a bowl of creamy cacio e pepe and a glass (or three) of Poggio Bonelli Chianti Villa Chigi 2016, I shared with her for what felt like the 187th time how my terrible, fitful sleep over the previous few weeks was really beginning to wear me down.

The truth?

My crappy sleep habits were actually wreaking havoc on my career.

Last Thursday was a typical night, I told her.

I woke up in the middle of the night with shoulder and neck pain. Again.

Tossed and turned for hours, couldn’t get back to sleep.

And the whole time I’m lying there, I’m stressing out more by the minute each time I look over at the clock, knowing I’m gonna have to go into work on the next day and give one of the most important presentations of my career, to our agency’s highest-profile potential client yet, on 3 freakin’ hours of sleep.

The stress and exhaustion made me want to weep.

“Well that sucks,” Ronda said.

I told her that wasn’t the worst of it.

After the presentation that Friday my boss called me into her office. Told me she didn’t think I brought my “A” game. Said if we don’t land this big account . . . then she kind of trailed off and didn’t say much else.

“Uh oh,” Ronda said.

Uh oh is right. Like me, Ronda’s worked in advertising. She knows the drill.

If the agency didn’t land this big client we’d been wooing for weeks, I might get fired.

“Crap, I can’t get fired, I just bought a house,” I said.

That’s when Ronda dropped the tough love.

“Kimberly, you’ve been complaining about this since early April. It’s now May. I told you 6 weeks ago about the Euphoria pillows I bought that totally eliminated my shoulder and neck pain. I told you how I’ve been sleeping through the night for the first time in years since buying them. I told you how I’ve never felt more well-rested. I waxed so poetic about these pillows you accused me of being a rep for the company. Hell, you even slept on one when you spent the night here a few weeks ago and said it was like sleeping on a cloud made of rainbows. BUY THESE PILLOWS, girlfriend.”

I’m embarrassed to say that’s when I nearly shouted, “But those pillows are $80 damn dollars a piece!”

With a sigh and what I swear was a little bit of an eye roll, she said, “Kimberly, I say this with love as your best friend: you can be kind of a miser sometimes. I know you spent well over $80 on this bottle of wine and the ingredients for the dinner you made us tonight. Why wouldn’t you spend $80 bucks on something that’s actually, you know, going to improve the quality of your life in an honest-to-god real way?”

I had to admit she was right.

“Oh alright,” I said, “give me the damn Euphoria Pillows website link. [à Link to website] And pour me another glass of Chianti.”

I’m happy to report that I ordered two Euphoria pillows that very night.

And while it took me a minute to get over the mild shock of spending $160 (I could buy four bottles of pretty decent Chianti for that sum), a few weeks on, I can say it was more than worth it.

Now I’m sleeping through the night for the first time in a very long time. I’ve never felt more well-rested. I’m ready to wax so poetic about these pillows you might accuse me of being a rep for the company.

And it’s not hyperbole to say that sleeping on Euphoria pillows is like sleeping on a cloud made of rainbows. [à Link to website]

Now, you might be asking yourself, “What the devil is Kimberly emailing me about pillows for? I got on this list to learn how to rock an ad agency career.”

But hear me out on this:

Think of superior quality pillows as a career enhancement tool.

That’s right.

A career enhancement tool, one of many in your arsenal.

You wouldn’t show up to the interview for the senior copywriter position at your dream agency with a resume written on a piece of paper ripped out of a spiral notebook would you?

Of course not.

You wouldn’t knock back two martinis at your agency welcome lunch the first day of your new job, right?

No. No, you wouldn’t. (Unless you’re Don Draper, in which case, you don’t need my career advice.)

So why would you rely on pillows that make it damn near impossible to get a quality night’s slumber, and potentially screw up your chance of landing & keeping that hot new agency career, all because crappy sleep prevents you from bringing your “A” game?

Don’t do that.

And don’t be me – don’t wait until a poor night’s sleep practically derails your career.

It just so happens that today – next Monday the exact kind of Euphoria Pillows I bought and swear by are on sale for $50 bucks off when you buy two.

$110 bucks to improve the quality of your life and, dare I say, your career prospects too.

Go on over to the Euphoria Pillows website right here, and get your $50 off today through Monday only. [à Link to website]

Your shiny new ad agency career prospects will thank you.

XO,

Kimberly, reformed miser

P.S. My hesitation about investing in Euphoria Pillows is now a small speck in the rearview mirror. It’s been overshadowed by 6 weeks of kick-ass quality sleep that’s seen my agency land that high-profile client (and I was even made the account lead after redeeming myself with a second presentation to the client last week, woohoo!).

Get your career-enhancement tool here for $50 off, through Monday only.

[END OF EMAIL COPY]

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So, there it is.

Once I knew my entry placed in the top five, the next step was to watch the video Chris and Kevin recorded breaking down the email and pointing out what worked and what didn’t.

If I’m honest, I was terrified to watch that video, and put it off for days.

Turns out, it wasn’t so bad. Everything they pointed out that needed improving was spot on, and super helpful to know.

Sure, I winced a couple times, but as Chris said in his review, “I’m being nitpicky, but yeah, you know, you’re on the leaderboard, so I reserve the right to be.” LOL.

Feedback from the Experts

(The feedback below comes from the video review Chris and Kevin did. I took notes while watching the video, so they’re a bit rough.)

Kevin’s feedback:

This had me hooked top to bottom.
Although you risked losing me in detail here…

Over a bowl of creamy cacio e pepe and a glass (or three) of Poggio Bonelli Chianti Villa Chigi 2016, I shared with her for what felt like the 187th time how my terrible, fitful sleep over the previous few weeks was really beginning to wear me down.

I love how you framed the value in STORY.

Really well done, @KimberlyHouston

Chris’s feedback:

First up, the weaknesses / what needed work …

He said the subject lines were just “ok/decent.” He said there was some curiosity in the main subject line I chose.

Curiosity is critical to persuasive copywriting, and subject lines are one of the key places we need to be using it. If your SL isn’t compelling, ain’t nobody gonna open that sales email, and you know what that means … no sales. ☹

He also called out this section, saying that I was erring on the side of “a little too much detail” –> Over a bowl of creamy cacio e pepe and a glass (or three) of Poggio Bonelli Chianti Villa Chigi 2016, I shared with her for what felt like the 187th time how my terrible, fitful sleep over the previous few weeks was really beginning to wear me down.

Detail is necessary and good, and it’s sadly missing in much of the underperforming copy I see when I do copy reviews. However, as Chris pointed out, “There’s a fine line into crossing into too much detail territory.”

He said he would break this up into two sentences –> And the whole time I’m lying there, I’m stressing out more by the minute each time I look over at the clock, knowing I’m gonna have to go into work on the next day and give one of the most important presentations of my career, to our agency’s highest-profile potential client yet, on 3 freakin’ hours of sleep.

I say this to my own clients all the time: If people see long blocks of uninterrupted copy, they’ll usually be turned off and not read it, so this is good to keep in mind, whether you’re writing web copy, sales emails, landing pages, or anything else you write for your business.

He said about this paragraph, “It’s ok, but a little much,” and suggested I might want to pare it down. –> “I told you how I’ve been sleeping through the night for the first time in years since buying them. I told you how I’ve never felt more well-rested. I waxed so poetic about these pillows you accused me of being a rep for the company. Hell, you even slept on one when you spent the night here a few weeks ago and said it was like sleeping on a cloud made of rainbows. BUY THESE PILLOWS, girlfriend.”  –> Oh, and he didn’t like the “wax poetic” thing either, lol.

Here he cautioned against using “wax so poetic,” again, and suggested I not overdo that. Ditto, “accuse me of being a rep for the company,” which he pointed out, “is kind of redundant from before, so let’s not have that twice.” –> Now I’m sleeping through the night for the first time in a very long time. I’ve never felt more well-rested. I’m ready to wax so poetic about these pillows you might accuse me of being a rep for the company.

Here he said, “Ok, I don’t really know what that means, but alright.” –> And it’s not hyperbole to say that sleeping on Euphoria pillows is like sleeping on a cloud made of rainbows.

He said to tighten this up a little. –> You wouldn’t show up to the interview for the senior copywriter position at your dream agency with a resume written on a piece of paper ripped out of a spiral notebook would you?

Here, he mentioned something that has always been one of my weaknesses as a writer – long sentences. Sometimes lengthy sentences are 100% necessary, but when writing copy, generally not. –>  So why would you rely on pillows that make it damn near impossible to get a quality night’s slumber, and potentially screw up your chance of landing & keeping that hot new agency career, all because crappy sleep prevents you from bringing your “A” game? –> “So Kimberly you really have this tendency to, you know, these long sentences. They’re ok. I mean, you have that, then you have a 3-word sentence, and then you have a medium-size sentence. [Which is good, he confirms] So with readability, let’s try to make this a little bit better.”

And here, Chris made a smart observation about how he would have done this differently. –>“Oh alright,” I said, “give me the damn Euphoria Pillows website link. And pour me another glass of Chianti.” –> He said, “Now here, I might handle this a little bit differently, I might transition and zoom out from the story. ‘You know, she was absolutely right. So I went to the website and actually I got a link for it right here.’ Blah, blah, blah, ‘you can buy it through my link. And it’s changed my life and here are the benefits,’ you know really quick, and then, ‘I think you should buy one too, and it’s honestly changed my life and I started sleeping better, my performance at work started improving,’ and blah, blah, blah. That’s how I would have probably taken it. Instead of putting the link in the dialogue, just segue directly into it.”

Finally, he pointed out the “the whole CTA (call to action) could be tightened up just a tad bit.”

And now, what worked about the email:

Chris said he liked the storytelling, and the one-to-one conversation. He said it was very natural and flow-y, “very email.”

He mentioned that a lot of people tried to shove a sales letter into an email in this challenge, and he told people not to do that; my email was a story-based email, “which was exactly what we were looking for.”

He said this was a great opener:

One Saturday night a few weeks ago, Ronda, my BFF of 30+ years, committed one of the kindest acts a trusted friend can ever do.

Chris –>  “It’s a great opening line, because it hooks you to the next one. And both lines pull you into the email copy. And that’s what you want to do at the beginning of an email.”

Here Chris said, “Yeah that’s a real fear, the fear of underperforming. There’s all these problems in people’s lives, how they manifest, how they appear, how they are dimensionalized in people’s lives, those are a good kind of demonstration.” –> After the presentation that Friday my boss called me into her office. Told me she didn’t think I brought my “A” game. Said if we don’t land this big account . . . then she kind of trailed off and didn’t say much else.

“Here you’re piling on the fear, but it’s ‘good fear,’ not like, ‘you’re gonna DIE!!!’ A lot of other people took that angle. But this is like a real fear.” –>  “Crap, I can’t get fired, I just bought a house,” I said.

“I like this because it’s telling your customer, ‘buy my thing!’” –>  “Kimberly, you’ve been complaining about this since early April. It’s now May. I told you 6 weeks ago about the Euphoria pillows I bought that totally eliminated my shoulder and neck pain.”

Here Chris pointed out, this is “an awesome way of handling an objection. This is a nice job.” –> With a sigh and what I swear was a little bit of an eye roll, she said, “Kimberly, I say this with love as your best friend: you can be kind of a miser sometimes. I know you spent well over $80 on this bottle of wine and the ingredients for the dinner you made us tonight. Why wouldn’t you spend $80 bucks on something that’s actually, you know, going to improve the quality of your life in an honest-to-god real way?”

He said this worked. –> And don’t be me – don’t wait until a poor night’s sleep practically derails your career.

And he liked this. –> Kimberly, reformed miser

And finally, re the P.S., he said, “Good, there’s some resolution to the story.”

P.S. My hesitation about investing in Euphoria Pillows is now a small speck in the rearview mirror. It’s been overshadowed by 6 weeks of kick-ass quality sleep that’s seen my agency land that high-profile client (and I was even made the account lead after redeeming myself with a second presentation to the client last week, woohoo!). I was even made the account lead after redeeming myself with a second presentation to the client last week, woohoo! –> Chris: “This is kind of aspirational, an implied benefit. People will read that and go, ‘I want that too.” They start to place themselves in your story and they’ll be like, ‘maybe if I . . .’ and they start to connect the dots. ‘Maybe if I get better sleep, I might perform better at work, and good things can happen for me too.’”

In the end, according to Chris –>“Overall, nice job. I thought this was strong, and demonstrative, and very email native I guess is maybe the right way to describe it. So, awesome job, Kimberly Houston.”

Key Takeaways

#1: Do things that scare you. I came very close to not entering this contest, for all the reasons mentioned at the top of the post. And if I hadn’t? I wouldn’t have honed my story-based sales email writing skills, I wouldn’t have gotten one-on-one feedback from two uber-successful & skilled copywriting experts (<– priceless), and I wouldn’t have a valuable piece of content to post to the blog.

#2: Get in a supportive community of your peers. To quote the Copy Chief guiding motto, “Nobody writes alone.” There’s nothing like knowing a wise and experienced group of industry peers has your back anytime you need help with challenges or problems in your business, or simply when you want to share a win. The Copy Chief community is about so much more than copy feedback. Copywriters, marketers and business people of all experience levels are there everyday providing feedback, answering questions, seeking answers to their own questions, and as an added bonus – having a damn good time doing it. It’s no exaggeration to say it feels like a family.

#3: If you want to write persuasive copy that sells, you must do the pre-work before ever putting fingers to keyboard. See above, “Prep I Did Before Writing.” This is imperative if you hope to connect with your ideal customers and convert them into buyers.

#4: When it comes to selling via email, stories tend to work better than strictly transactional emails. (NOT in every case, but in many.) You can probably see why. Would you rather read an interesting story that actually demonstrates how a product can improve your life in real-world ways, or an email that whose sole purpose is to sell, at all costs, and screams something like, “Our biggest pillow sale of the year!! 75% off through midnight tonight! Click here to buy now!”

Next time you’re writing an email to sell your products or services, consider using a story-based approach. It can be a lot more fun for you – and importantly, your audience – than writing a standard sales email. And it may get much better results, too.