The best SaaS onboarding emails for inactive users on a freemium trial

A subscription-based company wants to acquire high quality customers that stick around for a long time. And to build that kind of loyalty, a company needs to start somewhere. That’s why so many sign up pages require an email and first name — to add a personal touch to future messaging. But let’s be real, that’s only the tip of the iceberg.

The bulk of personalization happens in response to user activity. Someone signs up, takes a few actions, and some conditions are evaluated to determine that user’s core motivations. During the trial, that user receives a series of emails, in-app messages and push notifications to highlight features that are relevant to them.

But what about new users who bail right after signing up? Marketing campaigns designed to respond to user activity alone will fail in a scenario where people do nothing at all. There needs to be a fallback option.

To get a pulse on how other onboarding programs handle this scenario, I ran a short experiment with two dozen SaaS companies.

  1. I signed up for all 24 companies on the same day.
  2. During sign up, I skipped through the setup wizard and left the app as soon as I hit the dashboard.
  3. Some companies required email “activation”, so I did click through to activate those accounts.

That’s it. I checked in every few days and read the emails. My goal was to simulate a user that signed up but refused to take action within the app.

Me waiting for the big guns to show me how they operate

How SaaS companies handle inactive users

I selected an assortment of SaaS products for this experiment. As a marketing manager at a scheduling software company, I was particularly interested in seeing what our competition was up to. But I was sure to include companies from a variety of other fields including email marketing, form builders, CRMs, team management, etc.

The Control Group: Acuity, ScheduleOnce, YCBM, BookLikeABoss, Appointy, Doodle, SimplyBook.Me, Bookafy, ActiveCampaign, Airtable, Typeform, Asana, ServiceM8, Twilio, ConvertKit, Evernote, Dropbox, Wufoo, Zendesk, Todoist, 10to8, Meetingbird, Calendly, and Delighted.

Frequency of outbound messages

Most SaaS companies followed this email onboarding formula:

  1. The account activation email
  2. The welcome / Quick Start email
  3. The “we noticed you’re not using your account” email
  4. The app feature highlight + webinar email
  5. The trial ending / prompt to subscribe email

A five email series over the 15 day trial means a frequency of roughly one message every three days. That’s enough to be present but not smothering.

The majority of companies sent either a single email or 4–5 emails

As the graph above shows, 4–5 emails represented the average message frequency for an inactive trial user like me.

Half of the companies sent three emails or less. Roughly 20% of them sent only one email during the duration of the trial.

Typically these lean campaigns are made up of transactional emails only, aimed at account activation and trial ending. And since those users aren’t signing back into the app, both parties reach a stalemate by end of trial.

Neglecting new users means missing out on the future revenue that they represent. It may be better to communicate and risk being ignored than to make no effort at all.

The other extreme: Best Friends Forever strategy

There are also companies that overcompensate by sending daily messages to new users. Sometimes you get multiple emails in a single day and it feels like the company is a new crush that won’t leave you alone.

Four companies in my experiment sent me 11+ emails during my 15 day trial. I’ll give you a couple of examples here in greater detail.

One company with high message frequency was Convert Kit. I received a diverse collection of long form copy, webinar promotions, video tutorials, in-app feature callouts, and more. Their approach threw out a lot of hooks and tried to get me to bite. From their perspective, if those emails don’t drive engagement, I’m probably not their ideal customer anyway.

I also signed up for Todoist, who proceeded to send me 20 emails, the bulk of which were daily emails about account usage. 14 of the 20 email subjects were something like: Ezra’s task(s) for Oct 8 → 1 overdue.

The “1 task overdue” subject motivates engagement through a negative emotion. Every day of the trial that I didn’t engage, I saw a visual cue to sign in and take care of my unfinished business.

If that new user clicks into the email (maybe out of guilt), the actual body of these reminder emails contains helpful tips and feature highlights. The focus shifts from the overdue tasks to something more inspiring, with a link to log in and engage.

At the end of the day, ConvertKit and Todoist may have over-communicated but they still made a strong impression. They were two of the most memorable campaigns for me, because they offered so much.

Suffice to say, between one email and twenty, most companies seems to think 4–5 emails is the appropriate amount for an inactive user.

SaaS onboarding email templates

The account activation email

Of the 20 companies that sent an email on the first day, about half of them started our relationship with a request to click a confirmation link and activate the account. These emails were bland and to the point, looking something like this:


The “Confirm email” template

Why is the activation email so common? Because a person could type in anyone’s email address and use it to sign up for a service, but if the email is verified, it implies ownership and confirms an intent to engage.

But a word of warning — if the activation email comes too quickly, it can trigger an email notification that distracts the user from the setup wizard.

“Oh look, it’s an email saying I need to activate my account. But what if I lose where I’m at in the setup wizard? Umm…”

Activation should not disrupt the straight-line onboarding experience. Samuel Hulick has written about this problem in detail. So if you need to send an activation email, maybe let the user catch their breath for a moment. Several companies in this experiment waited an hour or more before sending their first email.

The end-of-trial email

The other standard transactional email comes at the end of trial. They don’t tend to have a lot of bells and whistled. They rarely seek to connect with the user’s needs on a personal level. Instead, they reiterate the value proposition with a call to action. Many of them resemble a “fill in the blank” template:

Example of a transactional end-of-trial email

The Welcome Email + Quick Start approach

Most companies that sent an activation email also sent a welcome email. They are the informative, warm and personal counterpart to the transactional message.

Ten of the twenty-four emails literally put the word welcome directly in their email subject — Welcome to [App Name] or Welcome to your [App Name] trial or Welcome, [First-Name].

Putting the word “welcome” in your subject makes it easy to differentiate the email from other messages in their inbox. But the Welcome Email formula doesn’t stop at its subject line.

Most SaaS welcome emails drive people toward a call to action: Start.

WUFOO welcome email teardown

The Welcome / Get Started email usually includes a login button to access your account. Some companies add a quick start guide, ranging from articles, videos, or deep links to an in-app dashboard.

Classic calls to action in a SaaS “Welcome” email

Welcome emails also tend to highlight an avenue for support, be it a knowledge base or live agent. But often the more personalized outreach comes later.

The sales demo disguised as a friendly personal note

After the email confirmation and welcome email, I typically saw one of two things. Companies either went the low-touch route and began highlighting key features or they went the high-touch route and came out swinging with a sales demo.

The second email that I received from email marketing tool ActiveCampaign, for example, had the subject “How can I help?” with a message signed by a real human. Included is a link to their scheduling tool, which would allow me to easily book a time without hassle.

The core offer is to learn more about the new user’s business/marketing goals. Behind that offer is the implication that the user will get value from sharing that information. These are sales emails, but very little ‘selling’ happens in the email body. That’s saved for later. The purpose of this email is to drive sales calls.

The “feature highlight” emails

In contrast to sales emails that are all about getting to know the user, the feature highlight email is focused on the app. These are the emails where companies get creative and put on a show for you.

Magnification is a great way to highlight a feature, as Dropbox does in this example

In a feature highlight email like the one above, you can expect to find most of the following:

  • A non-technical feature description that’s focused on the value it delivers to the user (as opposed to a technical, software-focused description)
  • A link the user can follow to either activate the feature directly or read an article about how to activate it
  • Optional: An image depicting the feature, be it a literal UI screenshot or a representational illustration

The Team Invite email

You won’t typically see this email until later in the sequence because it would be premature. A user typically needs to be activated and experience the value of the software before they feel comfortable inviting their team. Four of the 24 emails in the sequence had an invite team email. The earliest that I saw one was fourth in a company’s sequence, then fifth and eighth respectively.

Example of a Team Invite email from Asana

Account expansion is key to revenue growth and in many cases, it’s easier to get an existing company to add more team members than it is to get a new person to pull out their credit card and subscribe to your service.

Bonus: The sort-of-onboarding newsletter

Depending on the frequency of a company’s newsletter, it may or may not fall into your inbox during a two week trial. I received four newsletters during this experiment, two of them coming from ConverKit (but they’re a chatty bunch).

Happy with what you learned from this article? Smash that clap button and let me know if there’s anything you would have liked to seen covered in this piece. Or if you’d like to see another experiment, leave a comment and tell me know what you have in mind. Bonsoir!

Web Developer

Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store