Blog Startup Journey

A Look Inside Our Automated Onboarding Emails

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Automated emails are among our hardest-working tools. Here’s why.

Four years ago, we wrote an email.

That email, without us having to do anything, has now gone out to more than 30,000 people.

It’ll continue to go out to many thousands more.

And it’ll continue to help us grow our business without us ever having to click “send.”

The Power of Automated Onboarding Emails

The email I’m talking about is the “you’re in” email that every new Groove user receives.

The insights we’ve gotten from the responses to that email have been game-changing.

It’s part of our automated onboarding email drip, which we think of as the hardest working email marketer on our team.

It ensures that the next person who signs up will have the same experience as the next thousand, without any additional work on our part.

Our onboarding emails have helped us turn blog subscribers into trial users, and they’ve helped us increase our trial-to-paid conversions dramatically over the years.

To be completely upfront, we could—and should—be doing more with them. There’s a lot of opportunity here for us, and when we make them a priority and focus on them, we’ll take advantage of that opportunity.

But for now, we’re still reaping massive rewards from just a few days of work that we did a long time ago.

And so today, because I get so many questions about them, I want to share our onboarding emails to show you that even a little bit of time spent putting together an onboarding flow that makes sense can pay off in a big way.

Automated Emails for Blog Subscribers

We tested a few different approaches here to welcome new subscribers to our blog email list, and here’s the flow that has converted best:

On Signup

We start with a personal welcome email from me. It:

Day 2

The next day, we send an email with a link to our most popular posts. This makes it easier for someone new to our blog to dive in and start with the content that others have found most valuable.

Day 5

A few days later, we follow up with links to some of the guest posts we’ve published elsewhere around the web.

Day 9

Next comes an email introducing the reader to our Small Business Stack, a resource we’ve put together with discount offers from dozens of top SaaS apps for small business.

Day 12

Finally comes the ask. Here, we reiterate the value that we’ve delivered over the past couple of weeks, explain what Groove is and does, and invite the subscriber to try the app for free.

Around 10% of subscribers take advantage of that offer.

That number has stayed consistent as we’ve grown our list, which makes it pretty easy to understand why we focus so much on building more and better content: we can draw a very direct line from the success of our content to the success of our business.

So, to recap, our approach is this:

We continue to send some automated emails beyond this, which I’ll cover in another post (as I wouldn’t call it onboarding any longer).

Automated Emails for New Trial Users

With our blog drip, our goal is to get the subscriber to sign up to try Groove.

Once someone signs up for a free trial, we send them an entirely new drip, with the goal of helping them get as much value from Groove as possible, and ultimately becoming a paying customer.

There are a number of behavior-based triggers and secondary sequences in our onboarding flow, but for this post, I’m going to focus on the primary ones; the onboarding sequence that most users go through, as I think anyone that hasn’t put a lot of work into onboarding yet should start with a simple approach like this one before moving on to more complex setups.

I should note that this drip is supported by some product-related guidance that we put into the app itself, pre-populating every new Groove inbox with a series of messages that show the user how the app works.

On Signup

Just like our first blog email, this first message:

But most importantly, this email asks a critical question: why did you sign up?

With this question, we’ve been able to transform our messaging based on what we learned is most important to new customers, and we’ve been able to build deeper relationships with those customers by helping them with whatever unique goals or challenges drove them to sign up.

I still read—and act on—every single response I get to this email.

Day 2

The second email, which comes from Lesley, our Head of Customer Success, is short and sweet, with not much more than a short video that has some tips and tricks to help the user get more from the app.

Day 5

Custom profiles (that allow the user to pull customer data in from their own internal sources and display it in their customer’s profile in Groove) are a hugely valuable feature, but can be a bit of a challenge to set up if the user isn’t technically savvy. It’s the only feature in Groove with that limitation, but we know how valuable it can be to our users, so we make sure to address it in our onboarding flow with a step-by-step guide on how to make it work.

Day 16

A lot of customer success, for us, is helping users uncover features and use cases that may not have been obvious to them from the start. To do that, we try and capture a lot of stories about how customers are using Groove.

We share some of those stories in our automated emails, to give users new ideas, and to show them the value that they can get out of the product.

From here, there are a number of directions the flow can go, based on whether the user looks like they’re slipping away:

Or whether they’re very active and would benefit from upgrading:

Or whether they’ve abandoned us completely:

There are a few other paths, too. Ultimately, our approach here looks like this:

Our priorities are:

  1. Get the user to “success” as quickly as possible
  2. Bring back users who are slipping away
  3. Get as much information as we can, especially from users who are churning (or more likely to churn)

How to Apply This to Your Business

I hope that by sharing our onboarding sequences with you, I’ve given you some ideas for how to better think about your own automated emails.

We’ve got plenty of work to do—and improving this process never really ends—but these emails have worked very well for us so far, and I wish more businesses would take advantage of this approach.

Your users have invited you into their inbox, and you should take that invitation seriously. Use it to be useful, be interesting, and above all, help them succeed.

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From “aha” to “oh shit”, we’re sharing everything on our journey to $10M in annual revenue. We’re learning a lot and so will you.

About the Author

Alex Turnbull is the CEO & Founder of Groove (simple helpdesk software for small businesses) who loves to build startups and surf.

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