A Lesson on User Engagement From Don Draper

Whether you’re building a consumer app or B2B service, you know how critical user engagement is to your success. Strong user engagement is intertwined with healthy, growing revenue… while lackluster user engagement results in a spiral of churn. That’s a key part of why notifications and other product emails are such a powerful tool in any product team’s toolbox—email’s ability to connect with users and draw them back into apps is unmatched.

Yet, figuring out how to help your users take that plunge and develop an enduring, engaging relationship with your product is more subtle than “build it—or send it—and they will come.” Effective notifications and emails take a mix of technical savvy, great communication skills, and empathy for your users’ needs. If you’re a SaaS product manager or marketer, I’m sure you’ve often felt that it’s sometimes hard to do it all.

But what if we were able to bring in an expert who might have a few good words of advice on the matter…?

Scene 1 Act 1


A SaaS product team is gathered expectantly, murmuring, comparing lattes, when DON DRAPER enters the room. He takes a place at the head of the conference table, sits back, crosses his legs, smooths his tie, and surveys them coolly.

Don Draper:

Ladies and gentlemen. I understand you’ve got a problem. I’m here to solve it for you.

Product Manager:

Frankly, Don…is that okay? Can I call you Don? Thanks. Well, we’re stumped. We can’t ––

Don Draper:

Your app isn’t getting any traction. It’s not that it’s simply not selling. You’re not even getting a decent number of trials. Right? But it’s a good product. In fact, it’s a great product. (SPREADS HANDS) Why on earth isn’t anybody interested?

He leans forward, everyone rapt.

I know you’re all feeling the darkness here today. But there’s no reason to give in. No matter what you’ve heard, this process will not take years. In my heart, I know we cannot be defeated, because there is an answer that will open the door.

Product Manager:

Where…that sounds really familiar, for some reason..?

Don Draper:

Season six, episode eight.

Product Manager:


Don Draper:

The problem isn’t with your product. The problem isn’t with your market, either. You know in your hearts that people are practically dying to adopt a web-based smart document management system that combines standard tracking, check-in/check-out, inventory controls, rapid elasticity, and ubiquitous network access.

Product Manager:

Wow, you’ve got our platform down pat…

Don Draper:

I have no idea what any of that means. I hate computers. (STANDS UP, GOES TO EASEL) So it’s not the product or the prospect’s interest, the problem is that you’re not connecting the two.

A presentation board is on the easel, covered with a cloth. He whips the cloth away, revealing two columns of various words and phrases.

I’ve said it before, I think when we landed the Ford Edsel account: People want to be told what to do so badly that they’ll listen to anyone. Your problem is, you’re not telling them what to do. Instead, you’re not doing much of anything.

Points to the first column of words.

These are the calls-to-action you’re using right now, from your emails, buttons on your website, your PPC ads…wherever. This one, for instance: “Please explore more!” What are you suggesting, that they should sign up for the Boy Scouts? There’s no insistence, or confidence, and certainly no urgency. And we don’t want them to “learn” anything, we want them to go hands-on with the product, right this instant.

What’s a call-to-action supposed to be about? (WAITS) Anybody? Well, the textbook definition is, it’s an instruction to the audience to provoke an immediate response. But what is it really about? It’s really about action, motion, and power. So you use power words that give them a sense they’re doing just that – taking control, taking action, solving a problem, eliminating a pain point.

He points to the second column of words.

“Take your FREE trial now!” Because it’s theirs for the taking, because it’s something valuable we’re letting them have for nothing, and because they should grab it this second. Now! That’s a power word, and so is free, and take.

Or hit their emotions. Are they “worried about locating contracts?” or “sick of losing documents? Get the solution today!”

Give it value. Make the reward they’ll get for taking the action very plain. “Improve your ROI today.” Or if you can attach a real number, do it. “Join 100,000 satisfied users,” or “get 20% off before it’s too late.” If that sounds like retail, get over it. It works with business buyers, too.

Here’s another thing. Keep it short, and unequivocal. This ad banner of yours suggests they should “enjoy our 6-step tutorial series.” Will they be graded on a curve? Your buyer doesn’t have the time to spare to attend what sounds like a deadly dull extension class. Here’s what works: “Watch the video.” With a big “play” arrow graphic. And it takes them to a video that starts playing instantly. Period.

Product Manager:

I’m confused. You’re a guy who comes up with these killer taglines and beautiful slogans…

Don Draper:

No, what I do is convince people to buy your product. Whatever you say has to work in context. A CTA ought to always be short and absolutely clear, and uses power words to tell them exactly what to do next. If it gets any cleverer than that, you’re outsmarting yourself.

Which leads me to my last point. Test your CTAs and see what works, not just in the wording but in the value propositions or offers you put in front of people. I used to hate the account team when they did copy tests, but they had a point. Even the smallest adjustments can deliver a difference.

Product Manager:

Fantastic stuff, Don. Really. You’ve really opened our eyes.

Don Draper:

My pleasure. Mind if I smoke?

Product Manager:

Sure, just not inside the building.

Don Draper:

(SHAKING HEAD) Your century sucks.

What Did Don Teach Us About User Engagement?

So what are the lessons about user engagement our product team should take away from their meeting with our legendary, completely fictional ad man?

1. Never be afraid to bluntly, urgently direct your target into taking the exact action you want – they probably want to be shown the next step.

2. Use “power words” to get your message across.

3. Make sure your calls to action lets the target know there’s a reward for taking that action, whether it’s a clear product benefit or another incentive.

4. Keep it short, sweet, and to the point.

5. We all wish we could be Jon Hamm. Seriously.





SaaS User Engagement Tips

Increasing user engagement has become a mantra for SaaS product teams, and with good reason. That engagement is an essential quality of a high-growth product that retains customers and minimizes churn.

Recently, my colleague Amie highlighted how emails like welcome messages, activity notifications, and even password resets are an important tool for activating and retaining SaaS users.

But to be successful, product teams need to approach those emails with more care than the simple faith that “if you send it, they will come.” In fact, app teams can learn a lot about engagement from another group of people who’ve been using email to drive customer engagement for a long time: email marketers.

Here are three lessons from email marketing that can help product teams develop more effective email notifications and other app-generated messages.

1. Optimize relevance and deliverability

In email marketing, a basic metric of a message’s relevance to the target is its deliverability—that is to say, whether it even makes it to the user’s inbox. That sometimes surprises folks who aren’t steeped in the world of email, but here’s why it’s an issue.

When email doesn’t reach the inbox, it’s often for reasons more complex than a straightforward bounced email address. Mailbox providers like Gmail and Outlook use complex algorithms to assess whether you belong in user inboxes. These algorithms look at a spectrum of factors to determine whether your message should be tagged as a relevant message, a promotion, or junk.

We’ll drill down into some of these in the future, but there are already great deliverability resources for learning about everything from boosting sender reputation to SPF implementation.

It’s the same as in software design: If an app isn’t user-friendly or lacks sufficient utility, the user will delete it without a backward glance, exactly the same way they (or their email service provider) are hitting the spam button on irrelevant or badly-timed emails.

2. Use behavioral triggers

How do you promote retention as an engagement factor, whether in email marketing or software? By designing your campaign – or your product – to respond to the recipient or user’s behaviors.

In the case of email marketing, one example is to nurture people through the sales funnel by sending emails calibrated to their actions along that path.

Here’s an example from Groove, a help desk software provider. A user opening a trial account was the trigger for an email that welcomed them aboard with a personalized message from the customer support lead.  Did it work? Their conversion of trial users to paid users increased by 10%.

Exploiting behavioral triggers shouldn’t end once your users have been converted. Again, sustaining engagement over the long haul depends on conveying the right prompts at the right times. That’s a key factor in determining  the types of emails your product sends (and when).

In software product design, including unlocks or upgrades that reward trial, regular usage, or other actions is a common way of maintaining user engagement throughout a product’s lifecycle. Apply that same same growth hacking method to your product’s emails.

3. Test (and test again)

Perfecting the user experience—again, whether it’s in product design or email—means constant refinement, and that only comes from testing prototypes. That’s why the onboarding and notification mails your product sends should be tested as rigorously as you test your app’s UX (and your marketing team tests their promotional messages).

I mentioned how Groove used behavioral triggers as part of the email strategy for their product. They provide a good example of how to use testing, too, in how they optimized those behavioral emails:

The version above prompted users to open a free mailbox. The one below nudged them to try a product demo.


In all, according to Optimizely, Groove tested 22 different emails based on user triggers to get to the final six they sent during user trial periods. Testing like this is critical to optimizing an individual message or an entire campaign.

The lesson for SaaS teams? If you don’t test and refine your app’s notifications and engagement messages to make sure they actually connect and meet the real needs of users, you’re leaving a lot of potential engagement (and revenue!) on the table. Ineffective emails—whether marketing or product messages—squander one of your most precious resources: your users’ time and attention.

There’s more!

There are even more lessons to be had from email marketing that can help SaaS product teams increase user engagement via app notifications. In my next post, I’ll look at some of the specific qualities of good marketing emails that also can help product teams develop more effective alerts and notifications for their product.


See how @Zillow grew their email engagement by 161% w/ @SparkPost & @Iterable Click to Tweet
If it’s one thing I’ve learned in the past two years by working at SparkPost, it’s that there’s a clear difference between ‘delivered’ and ‘deliverability’ when talking about email. An email that’s delivered simply means an accepted transmission by the ISP has occurred. However, when measuring true email deliverability, we’re talking about measuring the success of getting into the Inbox vs. the spam/junk folder.

Email deliverability is a very important part of the equation for growth marketers wanting to crack the nut on email marketing. However, it’s not everything. Metrics such as open, click-to-open, and forwards are also important. Why? Because an engaged user is an ambassador for your brand. When we recently sat down with our customer, Zillow, they expressed interest in improving user engagement in their email marketing. Through regular conversations with their Technical Account Manager (TAM), we suggested they speak to our partner, Iterable. Iterable has been able to guide them in achieving better segmentation and increased open and click-to-open rates by 161% and 18%, respectively. Being able to test, scale, and nurture customers in real-time is essential to growth for Zillow and all companies.

In our recorded webinar , Beyond the Click: Essential Email Metrics that Drive User Engagement, please join us, Iterable and Zillow as we discuss Zillow’s unique approach to email.

In this upcoming webinar we’ll talk with Zillow to learn:

  • How deliverability helps increase user engagement
  • The approach Zillow took to increase their open rate by 161% and their click-to-open by 18%
  • Which email metrics to measure to boost your ROI
  • Why Zillow is able to make quick decisions based on real-time data

Get the recorded webcast today for Beyond the Click: Essential Email Metrics that Drive User Engagement.

In the meantime, you can read Iterable’s guest blog on how growth marketing can help increase user engagement by improving three email metrics.

~ Tracy Sestili
VP, Growth Marketing

9 Things ISPs Really Want Email Marketers to Know

Folding paper boats as symbol for onboarding email

Practical Examples of Onboarding Email

Your app has sung “Hello world!” Awesome! And now, customers are signing up. High fives all around—you deserve it.

But what now? Getting users to sign up is a big step, but it’s still only the start. Asking them to come back, get engaged, and convert into loyal customers takes more than a killer app. It also takes just the right onboarding flow.

Considering the onboarding experience is critical when introducing users to your product. Get it right, and you might nurture the next superfan. Get it wrong, and, well… crickets.

Fortunately, all of us already have one of the most effective onboarding tools out there: email. And building onboarding emails aren’t as hard as you might think. What they really take is empathy for your users’ point of view, a clear understanding of the problem your product solves, and a genuine and welcoming “voice” for your brand. Put those together, and you’ll find you have the recipe for success.

Here are five effective examples of email onboarding that will inspire you to start writing your own. I’ll tell you why they work and how you can apply them to get your own users on board and engaged.

1. The Opt-In

The first email you should send someone who’s just registered for an account is the email verification note. This serves two purposes. First, it’s a key way to verify that the email address the user provided is valid and working. Second, it serves as a confirmation that the user is choosing to sign up for your product (and opt-in for email communication related to your product).

Onboarding Email: Trello Opt-In

  • Who: Trello
  • Why it works: Starting with a clear and unambiguous subject line, this example gets right to the point and makes it easy for the user to perform the required action. The first name personalization and “If you didn’t…” explanation also reassures the recipient that this is a legitimate email. All the while, it stays true to Trello’s brand voice.
  • Room for improvement: An actual return address would be better than the do-not-reply sender address.

2. The First Step

Once a user has confirmed an email address, you’ll have a relatively limited window to get her or him engaged. The longer the delay between sign-up and action, the less likely your user is to become an active customer. So, make it easy to get started and reinforce the things that prompted him or her to sign up in the first place. There’s no time like the present to take the first step!

Onboarding Email: Pinterest First Step

  • Who: Pinterest
  • Why it works: An eye-catching subject line, clear prompting headline, and easy-to-click button all ensure this email is focused on encouraging a newbie user to give Pinterest a try. And even if the user puts off taking action, this email strongly reinforces Pinterest’s core brand voice, from subject line through the copywriting and the visual design. Bonus: the [email protected] sending address is smart enough to handle a wide range of possible user replies.
  • Room for improvement: I’d like to see first-name personalization in the copy. That personalization is an important driver of engagement—and something at which Pinterest truly excels.

3. The How-It-Works

Now that your customer has taken that first step, another key role of onboarding email is to explain how your product works, and what your user should expect. Don’t be tempted to provide a lengthy tutorial! Helping your customer see what to do at a glance goes a long ways toward simplifying the learning curve.


  • Who: ExpenseIt (from Concur)
  • Why it works: The visual design and copy—simple to scan, but deceptively substantive—work to keep this message easy to read. At a glance, the user can see how ExpenseIt works… and then dive in if interested. Throughout, key brand messages and the benefits of getting started are communicated. As a bonus, the checkmarks at the top of this email use a psychological incentive called the “endowed progress” effect to help motivate customers through a multi-step goal like getting started using the ExpenseIt app. Finally, [email protected] is a real address that can handle customer responses. No bounces for you!
  • Room for improvement: The subject line, though blandly pleasant, doesn’t create a clear incentive to open the email. It should be tweaked to create a compelling motivation to learn more about using the product.

 4. The Incentive

Subtle cues are all well and good, but at some point in the process of user engagement, it will be time to put your money where your mouth is. When used sparingly, rewards can be powerful motivators and communicate that that getting started with your product has tangible value. That incentive could take many forms—virtual currency in a game, a developer-friendly tchotchke, or even cold hard cash. It all depends upon what motivates your users and what their action is worth to you. (At SparkPost, for example, we offer a free t-shirt to new customers who have signed up for a free account, but who haven’t taken the key action of sending their first email within a certain amount of time.)

Onboarding Email: Ebates Incentive

  • Who: Ebates
  • Why it works: Ebates’ core value proposition is all about helping members earn cash rebates and save money as they shop at leading retailers. So, a cash incentive tied to shopping behavior is a perfect fit to help motivate new customers to get started. In addition, this email borrows a tip from “How It Works,” above, and conveys how easy it is to use Ebates and earn that cash back: 1-2-3. Finally, the look and feel of this email is very compatible with the overall Ebates brand: value-oriented, but also easy-to-use and second nature to what shoppers already do. (Props for also providing a working return address.)
  • Room for improvement: There are multiple calls-to-action here: shop now, learn more, as well as retailer-specific offers. Let’s zero in on one that’s most compatible with why users joined. Additionally, though the subject line is cheerful, it doesn’t give a clear message of just how easy it is to get started. For an action-oriented brand like Ebates, “welcome” isn’t what drives user engagement.

5. The Immersion

Finally, what if a site’s user engagement goal really is just that: to motivate engagement with their user experience and brand? More functionally- or commerce-oriented companies take a very pragmatic point of view when it comes to user engagement: has my customer performed action X or committed to transaction Y? However, content or social networking businesses realize long-term value from attention rather than transaction. For these products, reinforcing the brand and experience of the site is the core goal of onboarding email.


  • Who: Medium
  • Why it works: Medium is all about getting engaged with high-quality content. This new user email skips the marketing-talk and draws a reader into the sorts of long-form writing that’s made Medium a top content destination. It also provides an understated call-to-action to download the app or log into the Medium site in a way that won’t detract from the core reading experience. The content-rich, immersive experience of this email already reflects some of the preferences I established in my initial sign-up: when I registered, I had expressed interest in topics like entrepreneurialism. The personalized content in this first email reinforces the one-to-one nature of what Medium does.
  • Room for improvement: Truth be told, there’s a balance to be struck between personalizing and echoing. As a new user, I’d love to see what else Medium has to offer beyond the specific topics in which I expressed an interest. The subject line, though superficially personalized, doesn’t tell me what to expect from this email—there are better ways to draw the user in! Perhaps most importantly, this email doesn’t make a direct mention of how a new user can like, comment on, and create new Medium posts—that’s a missed opportunity for this onboarding email, because interactivity is key part of social networks like Medium. Finally, this particular example exhibits the bugaboo of a “noreply” sending address. Email is a two-way communication medium. Be sure your approach to email onboarding doesn’t leave a user without a means to communicate.

Are You Ready to Get Started with Onboarding Email?

Combined with in-app prompts, UX cues, and psychological incentives like gamification, email is a highly effective piece of the onboarding flow. These five examples show how you can use it at each step of the user engagement process.

I hope you’ve found these tips helpful for developing your own user onboarding strategy. By the way, do you have a great example of onboarding email to share? I’d love to see it!



P.S. If you liked this post, you might like these others in my onboarding email series:

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