Here’s What The Perfect Onboarding Message Looks Like

If your onboarding process fails to accomplish its goals, you run the risk of seeing a significant drop in retention. We have the solution

Matt Duczeminski
May 31 2018

A quality onboarding process serves three main purposes:

  • It showcases the immediate value and application of your product or service to your new users
  • It gets users off and running with your product or service quickly and efficiently
  • It continues to introduce new and advanced features as your users become acclimated with your product or service

If your onboarding process fails to accomplish even one of these goals, you run the risk of seeing a significant drop in retention at some point – typically before your users have even been exposed to everything your product/service has to offer.

Today we’re going to discuss how to create an onboarding messaging sequence that keeps your users engaged, motivated, and moving forward in their journey with your brand. With such a sequence in place, you’ll increase the potential for your users to become not just loyal followers of your brand, but also “power users” who get the absolute most out of everything you have to offer them.

Before we dive in, it’s important to note that there’s no “one-size-fits-all” approach to an onboarding messaging sequence. Not every user takes the same path when using a product or service. While some may go through each step of your onboarding process as you’d hoped, others may hesitate, get stuck, or otherwise need a little “hand holding” along their path to success. We’ll first go through the steps of the onboarding messaging sequence for the ideal user who does everything as expected, then discuss how to create messages meant to get “stuck” users back on track.

The Onboarding Messaging Sequence From Start to Finish

The “Welcome” Email

If you want to have any shot at keeping new customers onboard, you absolutely need to nail your Welcome Email. A study conducted by Experian found that welcome emails see 40% higher click rates and three times the transaction rates of typical promotional email messages. Essentially, this means you should expect a decent amount of your new users to open and take a glance at your welcome email. But, this also means you have your work cut out for you moving forward. After all, those who have taken the time to sign up for your services are certainly expecting you to follow through immediately. Unfortunately, a report by Ciceron found that an astounding 83% of brands fail to make a good impression via their welcome email.

So, the question is:

How do you create an effective welcome email?

To answer that question, let’s look at the anatomy of a basic welcome email.

Personalized, Inviting Subject Line

This is pretty straightforward:

By including your user’s name in the subject line of your welcome email, you can drastically increase the email’s open rate (by up to 26%, according to Experian).

To add to the human-to-human connection of the welcome email, you should also consider including your name, as well:


Chris Hexton, the CEO of Vero, lends his name to every welcome email the company sends out. As a result, these emails have an astounding open rate of 47%. Another way to reinforce the human-to-human nature of your welcome email via the subject line is to use inviting and engaging language that puts your new user at ease. Use words like “welcome,” “thanks,” and “for you” – and avoid spammy, salesy words like “bargain” or “free.” Also, avoid words that might make the user think of work (like “webinar” or “report”).

Thankful and Memory-Jogging Opening

Once a new user clicks on your welcome email, you want to immediately do two things:

  • Thank them for their time and business
  • Jog their memory as to who you are, and what you offer

Reinforce the personable nature of your brand – this time by thanking them for taking time out of their day to read your welcome email. Additionally, thank them for their business – even if they haven’t paid for your services just yet. Even if they haven’t given you money, they’ve still invested time and energy into the initial process – and have also provided you with their personal contact information, as well.

It’s essential to keep in mind that people are busy. Even if a user signed up for your services less than 24 hours ago, there’s no guarantee they’ll remember exactly who you are (as they may have signed up for a dozen other services within the same time period). Similarly, they may not get around to reading your email for a few days – in which case the same problem may present itself. This part of your welcome email doesn’t have to be anything too substantial. Simply provide a sentence or two thanking them for their business, and reminding them exactly what your company can do for them – then get them ready to move forward in their journey.

Set the User’s Expectations

There’s a decent chance that your new user isn’t all that clear as to what to expect from your company’s services. Perhaps the signed up on a whim just to check your brand out, or maybe they’ve already forgotten everything they’ve learned about your company; whatever the case may be, now’s the time to set the bar for their experiences moving forward.

Take a look at how text-editing app Notegraphy does so in its welcome email:


In addition to providing quick-hitting information regarding the app’s main features, Notegraphy’s welcome email also contains an instructional video. While not a necessity, including instructional media in your welcome email certainly won’t hurt your cause.

Prompt User to Take the Next Step

Your ultimate goal is to get your new user to actually utilize your services. But, since they’re brand new to your services, they might not exactly be sure how to get started at all. So, it’s your job to help them out.

Here’s how Groove does it:

(Source / Also note the personalization within this welcome email)

While the example above clearly provides a ton of support for new users, you might want to test using one CTA at a time in your own onboarding campaign at first. You don’t want to overwhelm your new users before they even get started.

(Source / One main CTA should be plenty)

The “Getting Started” Email

Once you’ve gotten past the initial formalities with your new user, you want to allow them to hit the ground running with your service.

Your “Getting Started” email should do three things:

  • Reinforce the value of your services
  • Provide instruction as to how to use your services
  • Offer options for receiving support

Here’s an example from Majestic:

(Source / Note how this example hits everything we just mentioned)

You won’t need to go too nuts when reinforcing your value; the user wouldn’t have gotten this far if they still needed convincing. But, again, it’s also good practice to err on the side of assuming your users might need a bit of a reminder. As we alluded to in the last section, you can either include instructional documentation within your “Getting Started” email or provide links to further learning within the body of the email. Whether that’s an ebook, a video, or any other type of content is up to you. Finally, provide a line of communication for your new users in case they need further assistance. Best practice: make this as direct as possible. You want your new users to know that an actual human being is prepared to help them at a moment’s notice.

Once you’ve provided your new user with everything they need to get started, you want to be on the lookout for their first “quick win.”

The “Milestone and Next Steps” Email

While the word “milestone” is typically reserved for more major accomplishments, for our purposes, a “milestone” can be fairly rudimentary.

The goals for a “Milestone” email are:

  • Provide positive reinforcement and celebrate your new user’s accomplishments
  • Correlate their ability to use your service successfully with the value they received from doing so
  • Introduce more advanced features, and get the user to engage further

Here’s Canva’s approach to the “Milestone” email:


In this email, Canva provides both intrinsic and extrinsic rewards to its relatively new customers. On the extrinsic side of things, the user receives a digital “trophy” (which, presumably, they can collect for accomplishing a variety of tasks within Canva). Intrinsically, they’re simply reminded of the fact that they’ve used this new service successfully numerous times.

Here’s another example of a “Milestone” email from Grammarly, which provides weekly updates on users’ progress:


Further along in the email, Grammarly provides some tips for how the user can improve their writing skills:

Also worth noting: the bottom of the email features a call to action for users to activate a number of advanced features that Grammarly has to offer. This addendum all but ensures that those who use Grammarly’s services will engage even further with the brand via these advanced features (that the user might not have even been aware of in the first place). These advanced features might be part of the services a user currently receives (and, again, which they might only now just be ready for), or they might be part of an advanced service package. Which leads us to the next email in the onboarding sequence…

The “Upsell” Email

The “Upsell” email is similar in fashion to the “Milestone/Next Steps” email, but it includes a few extra nuances that are worth diving into. Like the previous email in the sequence, your “Upsell” email should begin by reinforcing your user’s accomplishments and the value they’ve received from your services. In addition, it should also motivate the user to push themselves to accomplish even more – and give your service’s advanced features a shot.

Here’s an example from Evernote:


And another from Wix:


In both of these examples, it’s clear the user has been getting decent value from either service – but there’s definitely a lot more they could be doing with them. Not only do these emails showcase what the user will be able to do, but they also explain what the user will get out of doing so. And, again notice the clear calls-to-action, which make it incredibly easy for the user to take the next steps whenever they’re ready.

Nudges, Reminders, and Winbacks

Now, as we said earlier, there’s no guarantee that your users will go through each of these steps without some issue or contingency arising. In fact, it’s probably more likely that most of your users won’t go through the onboarding process seamlessly. With that in mind, you’ll want to have a number of “nudge” or “reminder” email templates prepared for when a user remains inactive for a certain period of time.

This includes inaction between:

  • Your “Welcome” and “Getting Started” emails
  • Your “Getting Started” and “Milestone” emails
  • Your “Milestone” and “Upsell” emails (or after your “Upsell” email)

Your goal is to get the user back on track and using your services to achieve their goals. Here’s an example from ProjectMap, in which the company is contacting a user who has yet to reach their first milestone with the service:


With a short, personable, and to-the-point email, ProjectMap does three things here:

  • Reminds the user where they left off
  • Tells them what they need to do to get rolling
  • Explains what they’ll be able to do once they take that next step

Here’s another example from StruckAxiom, which we’ve referred to before in our article on winning back at-risk customers:

While this email is more tailored for a blast announcement to an entire mailing list (or segment), it can certainly work as a way of bringing back individual customers who have been inactive for some time, as well.

One last type of “Nudge” email worth discussing is the “Reasons Why” email, which, as the name implies, provides a number of reasons why a user should reconsider engaging with the brand in question:


Unlike the sequential messages we discussed earlier, “nudge” and “reminder” emails, by nature, aren’t sent after the user takes a specific action. On the contrary, they’re meant to be sent when a user has been inactive for a certain period of time. The question is how long should you wait before sending these reminders?

Truthfully, the best answer we can give you is:

It depends.

For one thing, it depends on a number of metrics, such as the average amount of time it typically takes your new users to reach their first milestone. If you send the reminder too early, it might overwhelm users who feel like they should be further along in the process than they actually are; if you send it too late, they may have already lost interest. The best course of action then, is to measure, test, and tweak the timing of your reminder over time, and continue to improve your understanding of what works best for your users. As with all things marketing, you want to know with near-certainty that you’re delivering the right message to the right person – at exactly the right time for them.

The “Exit” Email

Unfortunately, losing at least some of your customers is an unavoidable part of running a business of any kind. If a user specifically requests that their account with your company be closed, you certainly want to honor their request. But, as the saying goes, goodbye doesn’t have to be forever. At the very least, you want to part ways amicably, opening the door for a potential reunion some time down the road. You can also take this time to learn why, exactly, the user decided to part ways – and pledge to make improvements moving forward.

Here’s how Groove does it:


With one short, empathetic, and grateful message, Groove was able to reach out to and connect with their dissatisfied clients – and collect a ton of information from them in the process.

So, while losing customers certainly isn’t ideal, you definitely want to include an “Exit” email within your onboarding playbook. As the owner of a company, the only thing worse than losing a customer is not learning anything from losing them.

A proper onboarding messaging sequence allows you to walk with your new users on their path to success with your product or service – and to make sure they keep pressing forward, even when the going gets tough. The main thing to keep in mind when crafting any of the above-mentioned emails is to focus not on prodding your user along, but on providing the support they need to move forward on their own terms. Though you certainly want to make clear that you’re prepared to provide support as needed, you also want your users to feel more than comfortable using your services all on their own.

The guide to advanced customer segmentation


Matt Duczeminski

Matt is a professional writer specializing in helping entrepreneurs improve relationships with their customers. He lives in Philadelphia with his wife, Sarah, and he'd probably get a lot more work done if his cat would stop bothering him.

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