Email Marketing

The Game of Thrones Approach to Powerful SaaS Free Trial Emails

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Too often SaaS companies take a middle-of-the-road approach to their free trial emails. If you’re not seeing 20% or more in your conversion rate, this is likely your approach.

To which I say, consider Theon, son of the Ironborn king, in Game of Thrones. Stand for something — like proving yourself to your cruel dad — or risk dying for anything.

Instead of a slow death, you need to take a level-headed, fight-to-the-death approach. Like Daenerys Targaryen in her mission to reclaim the Iron Throne in the nearly bankrupt city of King’s Landing.

Is your SaaS company leaking money out of its free trials due to a poor conversion rate? Also, are you fighting against your own version of the Whitewalkers: cold, heartless churn.

If so, steal the Game of Thrones’ three-pronged approach to world domination and apply it to your SaaS free trial emails to boost conversions.

1. Start with your end goal in the crosshairs

You can’t plant your bum on the Iron Throne in three steps. If it were that easy, there’d be a rapid succession of rulers over Westeros. In the Game of Thrones, you need a detailed, clever strategy to claim the Iron Throne.

Likewise, you can’t persuade a trial user to whip out their credit card if you don’t have a plan in place.

Patrick McKenzie says that 40-60% of users who sign up for a free trial will use it once and never come back. Your Game of Thrones approach to combat this issue is to be merciless in your strategy.

You want the Iron Throne, the biggest throne in the land. So start with that end goal in the crosshairs: a free trial conversion rate of more than 25%.

How do you accomplish this goal? By careful, deliberate strategy. Plot out your moves and checkmates before wading into battle. You should know your long game… and your short game. Plus, all the steps in between.

In Game of Thrones, strategy means knowing your territory and the scope of the land. Winging it doesn’t work. The stakes are high: a poor strategy gets you killed.

As Sun Tsu said,

“Strategy without tactics is the slowest route to victory. Tactics without strategy is the noise before defeat.”

A good warrior knows his enemies and their weaknesses. He knows how to exploit those weaknesses, like defeating Casterly Rock by sneaking in through the sewer. He also knows his allies and how to best use them.

Daenerys has a mind for strategy.

She started at the bottom and stair-stepped her way to greatness. She won over the Dothraki, moved to freeing the Unsullied, and honed her skills in several foreign destinations.

Only then did she move to conquering King’s Landing.

For SaaS free trial emails, it’s the same. Converting free trial users to paying customers is your company’s lifeblood.

Your strategy to paid conversions has five key elements:

  • Assign one goal for each email in your sequence
  • Assign one goal for your free trial sequence
  • Understand your USP
  • Know your milestones
  • Stir your trial user’s heartstrings

Assign one goal for each email in your sequence

To translate it into Game of Thrones language, having one goal for each email is knowing your territory. When you have a specific goal for each email, you can tell which email is performing and which one isn’t.

You can’t craft a killer email if you don’t know why you’re sending it, says Isaac Moche of HubSpot. So pick a goal that’s more business-driven than a click rate or an open rate.

Sticking to one goal helps you — and your readers — focus. In this email from Wistia, you know exactly what you need to do: upload your first video.

Just as you can’t take your army and expect them to successfully attack King’s Landing, Winterfell, and the Wall at once, focus on one goal for each email, then move on to your next goal and next email.

Assign one goal for your free trial sequence

Give your free trial sequence one goal; otherwise, you’ll never know when you’ve reached success.

Sophia Bernazzani explains this concept:

“If you don’t have a goal in mind for the emails you’re sending, the recipients won’t know what the goal is, either. Once you define a goal for your email sends, you can define success and build a list to make that happen.”

The goal for your free trial emails is specific to your software.

Perhaps your goal is your trial user reaches their Aha Moment. Or if your Aha Moment happens early for your app, perhaps your goal is a paid conversion.

Understand your USP

In season 7 of HBO’s Game of Thrones — not to be confused with the books which haven’t reached book 7 yet — Olenna Tyrell told Jaime Lannister that she was the one who poisoned King Joffrey.

Jamie’s jaw dropped. His eyes went black. His good hand clenched his sword.

You could see that he regretted giving her the mercy of a painless death.

If Cersei and Jaime had known what their competitors, House Tyrell, were doing at the time, they might have prevented their firstborn son’s horrible death.

The takeaway? Analyze your competitors to know what they’re doing. Or not doing.

Then, using that information, analyze your software and company. Figure out what makes you different in a sea of wannabe warriors.

This is the core idea behind your sigil (a symbol used in magic) or brand.

You want to find your USP (unique selling proposition) or what your business stands for.

You know exactly what Raven does thanks to the points I underlined in red.

Instead of trying to be known for everything, Joseph Putnam says, your business stands for something specific. That becomes what you’re known for.

When you try to be known for everything, you’re known for nothing.

Know your milestones

For a Game of Thrones player killing to sit on the Iron Throne, this means conquering each of the lords holding the strongholds scattered across Westeros.

Each castle stronghold is a milestone in the winning strategy of being Ruler of Westeros.

Two of the most important milestones in your user’s journey, says Len Markidan of GrooveHQ, are the moment they sign up for your product and the moment they achieve their first success with your product.

You can orchestrate the steps involved in reaching that second important milestone (aka your user’s Aha Moment).

As Tommy Walker explains in this fantastic article, you should be asking two big questions:

  • What is the primary action(s) you want your user to take within the app?
  • What steps does your trial user need to take to reach that goal?

For your SaaS free trial emails, your milestones are determined by your Aha Moment. That, in turn, dictates your onboarding process and the content for your free trial emails.

Your user’s in-app actions should work in concert with your free trial emails. As Rob Walling, Drip’s founder and CEO, says,

Figure out the minimum path to awesome, do it in-app, then tell them again via email. This is the tell them again via email part. We have just five emails that go out to our trial users. You’ll see that open rates on these things are shocking: 68%. Even the bottom one’s 59%. We really get high open rates on it. The text of these emails is something similar to this, “Drip’s goal is to help you make more money. Your free trial is x days long, and these are the three steps to get set up.”

Stir your trial user’s heartstrings

Emotions are a heavy hitter in helping us make decisions.

Research shows that we make decisions based on emotion, then use logic to come up with a reason for that decision. Gerald Zaltman, Harvard Business School professor, says that 95% of our purchase decision-making takes place subconsciously in the emotional, intuitive side of our brains.

Both Jon Snow and Daenerys use emotion to their great advantage. Think of the heart-clenching moment when Jon faced the entire Ramsey Bolton’s army solo, sword raised high, ready to wade out and meet his death.

Talk about super motivation for his troops to see their commander prepared to fight. Alone.

Or consider Daenerys’ dragons and stomach-clenching rush of fear when they swoop low from the clouds, breathing fire. You want to be part of her epic story… and run like hell.

Emotions are powerful. And your SaaS free trial emails need their power to convert.

Here are two ways to build in emotion:

1. Trigger emotion with your trial user’s Aha Moment

Pinpoint that one moment when your free trial user realizes the true value of your software in their life. That’s your Aha Moment. It’s also emotional.

A growth team should focus on one operational metric, according to Nabeel Hyatt, VC at Spark Capital. Make sure that metric is concrete and relatively early in your trial user’s experience of your software.

Chamath Palihapitiya, in charge of growth at Facebook, warns against measuring time to the Aha Moment in days. Instead, you should measure it in hours. Or minutes and seconds.

Your aim is to get your trial user to an Aha Moment as soon as humanly possible after signup.

In this email from Wistia, adding a video is my first step toward my Aha Moment.

I’m off to upload my first video, so I can pat myself on the back. That’s a good feeling.

2. Build in a progress indicator

You’ll evoke positive emotions in your trial users by using a progress indicator. Show their onboarding progress in two ways: a progress email or progress bar in-app.

A progress indicator is a fantastic way to keep your users happy and engaged — two emotions you want associated with your software. Talia Wolf recommends showing your customers reports, numbers, and data on their achievements via your service.

Check out my progress report from Nest, showing me how many hours I had the A/C on.

Nest energy consumption email

Reading this email, I feel pretty special. Look at how well I’m doing and all the leafs I earned.

This is key for happier, more contented customers.

This is my progress bar in Active Campaign. I’m more than halfway done with onboarding.

You can implement a progress bar in your in-app onboarding process. Drip did and saw a trial to paid conversion rate increase of 2.5x.

2. Reinvent yourself when needed

When Jaime Lannister’s fighting hand was chopped off, he could have quit. He could have rested on his infamous laurels of being a Kingslayer. He could have gotten drunk every day for the rest of his days.

He didn’t.

Instead, he learned how to fight with his other hand and got back out there.

Or take Sansa Stark who began the Game of Thrones as an innocent young girl viewing the world through rose-colored glasses. Now she’s stand-in King of the North for Jon Snow, wise to Cersei’s cruel ways and Littlefinger’s manipulations.

Or Daenerys who started off as a scared pawn in her older brother’s game, sold off as a young bride to the Dothraki ruler.

Now she’s Mother of Dragons, etc., etc. Honestly, I’m not as skilled at rattling off her titles as well as Missandei, her handmaiden, is.

Arya Stark is the queen of reinvention. Even though she’s one of the younger characters, she’s already done all this:

  • She has been an aristocrat’s daughter
  • She has been a servant in Walder Frey’s household
  • She has been a boy (in disguise)
  • She has traveled to Braavosi
  • She has been a religious servant (which was weird)
  • She has traveled home to Westeros
  • She has been on a mission to kill Queen Cersei
  • She has been a warrior by killing dozens of men

Reinvention is a key theme in Game of Thrones. It should be the same for your SaaS free trial emails.

Even IBM — a great, huge company — agrees. They reinvented themselves from a computer seller, suffering the then-biggest loss of $8 billion in 1993. They reinvented themselves to become the number one seller of enterprise server solutions in the world by 2013, just twenty years later.

Your free trial emails aren’t working? Reinvent your emails.

Here are a few ways:

Go with long copy: Joe Sugarman recommends long copy to justify a higher price or to illustrate the benefits of an unusual product.

Find a better customer story: Terry Dean says that a case study is the easiest story to tell by email. Contact some of your happy customers, ask how they found your software, what results they had, and how their life looks now. Are any of your customers using your software in a unique way? Tell those stories.

Lackluster open rates? Analyze that email’s subject line or “from” name. Users don’t open emails from people they don’t recognize. Test “from” names like “John Smith from AppName” or “John from AppName.” Ensure your email’s body copy fulfills the promise from your subject line.

Poor click-through rates? Examine your body copy and make sure each line of your email leads your user to read the next line. Check out your CTAs and how many you have. More choices (or CTAs) lead to paralysis and less action as research has shown.

Switch up delivery of your emails: Time-based email series are easier to plan and write, but triggered emails have a click rate of 151% higher than other emails.

As Lincoln Murphy of Sixteen Ventures says, “If you’re still sending emails based on a timed sequence instead of triggered by actual user behavior, you’re 100 percent doing it wrong.”

Use a message of “do this to get this result” in your emails. Avoid conveying the message of “do this, do this.” Those items pile up into a huge to-do list that looks like a lot of work. No one wants more work in their day.

For example, check out this email from Bitly.

Yes, please. I do want to see who is clicking my links. And it doesn’t feel like work.

Keep in mind that you’re trying to change behavior. People will revert to old behavior because it’s easier.

Be proactive when spotting warning signs

If you notice early signs of churn, like non-use, take a proactive approach, as the best-in-class SaaS companies do.

Here’s how: Map out your ideal customer flow and use analytics to find exactly where your users are dropping off. Write an email to that trial user to inspire them to take their next step.

Send out an email like this one from

Once you’ve found an email that works, A/B test it.

Andrew Chen recommends prioritizing the input variable and trying to increase it. This could possibly be at the expense of something else. Test if those trial users are more successful in terms of your sequence’s one goal as a result.

Don’t get discouraged if you don’t see immediate results.

Reinvention and testing take time. Jaime Lannister got beaten by Bronn of Blackwater repeatedly, until he learned how to fight with his other hand.

Are you playing too soft?

If your SaaS free trial emails aren’t converting well, the bigger picture could be that you’re playing too soft.

I sign up for a bunch of free trials. Many of the free trial emails I see don’t have 3 important emails: strong pitch emails, winback emails, or survey emails to non-converting users.

Send strong pitch emails

In this email, make your strongest case for why your trial user should become a paying customer. Give them powerful reasons. What would you tell your best friend if you wanted them to sign up for your software?

Put that in your pitch email. Then layer in persuasion tactics. (More on those below.)

Check out this email from Pipedrive. It was sent two days before my trial was to end.

No, I’m not panicking right now because my trial ends. Honestly, I can’t remember what your software does… or why I should care…

Instead, tell me how my business grows, that I close more sales with your software, and make more money. I care a lot about those things. And this is the email where you should do that in a big, bad way.

Your trial user doesn’t want you to hold back in your pitch email.

Send winback emails

At least 90% of the free trial emails I see don’t have a winback email. That’s a problem.

Think of your winback email as another pitch email. This is your second shot at highlighting how your software will make your trial user’s life better, easier, more awesome.

Check out this email from BuzzSumo. It’s short, sweet, and to the point. It makes me want to reply and say, “yes.”

Remind your trial user of what your product does, back it up with stories and testimonials, then give them a reason to sign up.

Survey users who didn’t convert

In this Quora feed, Steven Moody recommends sending a survey to the free trial users who didn’t convert.

A survey gives you valuable feedback about your trial user’s loss of interest on two important fronts: 1) whether it was something you could have avoided, or 2) whether it was something you can fix.

GrooveHQ sent out an exit survey via a simple email to grow their customer exit survey responses by 785%.

They tested roughly half a dozen variants of that email. The winning email had one slight change. Instead of “why did you cancel?” they asked “what made you cancel?”

That tiny difference in framing almost doubled conversions, resulting in a 19% response rate.

Play to your trial user’s motivations

Melisandre, the Red Priestess of the Lord of Light, uses this method on Stannis repeatedly. He wants the Iron Throne. She convinces him to sacrifice his only child and attack King’s Landing at a poor time.

You’re aiming to do the same thing to your trial user. Only in a much kinder way and without the fear of death.

Once you beef up your trial email sequence, use persuasion tactics to play to your trial user’s motivations.


Jack Malcolm says, “Framing is a way of presenting your message in such a way that listeners see it one way as opposed to another.”

Facts have meaning only in comparison to other facts, so choose those other facts wisely.

For example, when Jack Welch took over at GE, he challenged business unit heads to be number one or two in their industry. Suddenly, the fact that most divisions at GE performed well compared to their industries didn’t look as good.

Cersei is a master at framing. Usually, she uses it to get her listener to do something they don’t want to do.

She describes where her listener is now and compares it to what will happen if they don’t do what she wants.

Future pacing

This tactic is used by top persuasion leaders like Bill Clinton, Martin Luther King, Jr., and Tony Robbins.

To future pace, you need to do three things:

    1. Acknowledge the trial user’s current position to smooth resistance
    2. Use the word “imagine” with a clear time frame
    3. Recognize where the trial user will end up

For #2, take your trial user to a particular event in the future where they are using your software. Use this formula: “Imagine (fill in a particular time) from now…”

Check out this email from CoSchedule that does an awesome job.

In your free trial email sequence, dedicate an email to future pacing. Be specific in the scenario you ask the user to imagine.

End with recognizing where the user will end up by using phrases like “That would be great!” or “That would be a new level of business for you.”

What your user’s life looks like if he doesn’t change

As Sophia Le says,

Sometimes missing out on benefits isn’t enough. It might be a proven fact that your product’s feature has helped others. But sometimes it’s not enough to persuade the skeptical trial user. So you need to change their mindset. You need to illustrate what would happen to the user if they choose to pay for your product… and how life would be if they didn’t.

Tell a story

Storytelling is one of the most powerful persuasion tactics, but it’s rarely done well.

Use the Hero’s Journey — the foundation for Hollywood blockbusters like Star Wars, Harry Potter, and Guardians of the Galaxy — to nail storytelling in your free trial emails.

This story framework has three parts:

      1. The world before: paint a picture of your free trial user’s world as it was.
      2. The drama: show the drama that created a shift in your user’s world.
      3. Resolution: show them how your product can be a resolution to the drama. Their world is good again.

Use the Hero’s Journey framework over several emails. Your CTA is to prompt your trial user to log back into the app as the next step in their journey.

Or use this framework in one email, like Derek Halpern did in this email:

Evoke emotion for decisions

Emotions play a key role in our decision-making process.

Think about all the decisions made on Game of Thrones. How many were emotion-based? Tons.

We invest our money in products, experiences, and services that make us feel a certain way, says Talia Wolf, such as feeling loved, safe, appreciated, strong, or perhaps just better than others.

You want to know the “why” behind your customer’s buying decision.

Interviews are a great way to figure out this motivation. She recommends interviewing your customers and your teammates who have a daily or weekly touch-point with your customers.

3. Exploit your strengths

“You’re not a sheep. You’re a dragon,” said Olenna Tyrell to Daenerys. “Be a dragon.”

Each family in Game of Thrones has its own defining feature. The Lannisters are cold and calculating. Starks are honest and smarter than generally regarded. Ironborn are fierce and brutal.

What sets your software apart?

What is your software’s defining feature? Understand what makes you different from your competitors and how that adds value to your user’s life.

Don’t be shy about saying what makes you different, especially when you’re the only solution that does X like you do.

Evaluate your software and its strengths. They could be:

      • Strong onboarding series that educates
      • Triggered free trial emails
      • Killer customer service team
      • Proactive winback emails
      • Awesome storytelling

Figure out what makes your software different by:

      • Asking your customers
      • Asking your users who left
      • Asking your newest users why they chose you (i.e., what they’re hoping to get)
      • Using Jobs to Be Done framework

Just because everyone else is writing a certain thing in their emails, is that the right thing for your business?

Deploy your emails

Take a lesson from Ned Stark: use the tools at your disposal instead of losing your head. (Pun intended… still too soon?)

Petyr “Littlefinger” Baelish and Lord Varys are perfect examples. Neither one is physically imposing or great warriors. But they’ve gained a lot of power. They are at the right-hand of leaders like Daenerys and Jon.

Use your strengths in a smart manner that deploys them to their greatest power, like Sansa does with Brienne of Tarth. In your free trial, emails are your greatest strength.

If you’re going to do one thing, do the emails, says Rob Walling, founder and CEO at Drip. “That’s the one that I’ve seen game-change the most apps.”

Matt Duxbury agrees that email is one of the best ways to reach out to people before, during, and after the free trial period:

“Don’t underestimate the power of communicating via a prospect’s inbox.”

How to plan your free trial email sequence

Determine your trial user’s Aha Moment. In-app, guide them through each step needed to achieve it. Guide them through each step again via email. Then offer to do each step with them via a support call.

Above all, use your strengths… and your free trial emails.

Game of Thrones began because…

Robert Baratheon got fat and lazy.

Before he was King of the Iron Throne, he took down the previous ruler.

That ruler was a king who rode fire-breathing dragons, a king who was the centuries-long legacy of the Targaryen house that had ruled Westeros. King Robert was awesome. And then he got sloppy, drunk, and gored by a boar.

Take a lesson from Robert and strive for improvement in your SaaS free trial emails. Once you think you’re on your Iron Throne, find a new goal and a new conversion rate. And work for it.

About the Author: Laura Lopuch helps SaaS companies attract new leads via cold emails and convert free trial users to paying customers. She swears by a storytelling approach for emails so that they are gotta-take-action persuasive. As a former senior litigation paralegal, she used emails as her secret weapon to convince people when they’d rather say “nope.” Revolutionize your welcome email against boring nothingness with this must-have checklist.

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