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SaaS Email Onboarding Teardown — Hey.Space

In the last six months since we launched Encharge, I had the pleasure to dissect dozens of email onboarding flows. From solo-founders who are just getting into the dreadful and wonderful world of software, to some of the largest players in their respective product category.

And there’s one common thing that they all share:

Their email onboarding was not thaaat great.

All of the onboarding flows that I’ve audited ranged from solid mediocre to pretty much non-existent.


All of the teams had an enduring passion for fixing their onboarding and increasing their conversion rates.

Before you judge me for sounding like a grumpy old email critic (if this is even a real vocation), let me be clear:

I don’t blame these companies even a single bit!

Building an effective, relevant, segmented, action-driven email onboarding for a SaaS (software as a service) is probably one of the hardest projects a marketer needs to deal with in their career.

It will challenge your technical knowledge, logical mindset, copywriting creativity, people’s skills, and patience. Oh, yeah, patience — you have to be very, very patient to see this baby walking.

So before I plunge into the truth, let’s be clear that I don’t aim to bash anyone.

Neither I expect you to apply all of the tips I share here right off the bat. I hate it when marketing consultants give a bunch of super-hard to execute tips like “Send a re-engagement email to all people that have signed up for your tool but haven’t submitted at least 3 requests in the last 7 days.”

I’m not leaving you alone in this! I plan on providing technical guides on how to implement my tips. Also, I share some low-hanging fruit ideas that you can implement as long as you have access to your emails.

Now, as I spilled the beans, I’ll dive into the first article from this new series — the SaaS email onboarding teardown. The first one that I’m going to review is HeySpace.

HeySpace Overview

HeySpace clean slate screen

If Slack and Trello had a beautiful baby, it would be called HeySpace. It’s a gorgeous looking web and mobile app tool that allows you to chat and work on your projects in a single workspace.

Their in-app onboarding is pretty good, but the onboarding emails need work!

So let’s look under the hood:

  • 3 emails in total
  • 1 event/action-triggered email
  • 4 in-app messages

I know the HeySpace team is currently doing a total overhaul of their email onboarding, so let’s be fair with them! That being said, I thought this could be a good opportunity to show how I would handle designing an email onboarding from the ground up if I had very little to work with.

The audit is broken into two sections: an audit of their current emails and Money-making tips — my top-level suggestions that could really move the needle for HeySpace.

Current Emails Audit

Email #1: Welcome Email

When: After signup

Zrzut ekranu 2020 02 04 o 13.00.09

The personal approach in this email is great; the picture of Damian and his kind welcome.

We need to fix a couple of things with that email.

1) Apply the formula of email simplicity

In emails, we usually recommend one Call to Action (CTA) per email to avoid decision paralysis and increase click-through rate (CTR) for your desired outcome.

Your welcome email message is going to be your most opened email (40-60% average open rate). It may feel tempting to cram in every little bit of information into it — intros, features, next steps, multiple prompts, a survey, and whatnot. I encourage you to avoid this unless you want to confuse your users and reduce the CTR of your most important outcome.

Best you can do is follow the formula of email simplicity:

1 Email = 1 Goal (for you) = 1 Desired Outcome (for the user)  = 1 Call to Action

Going back to HeySpace, I’d take out the “Explore my account” button and emphasize the “Schedule a meeting” CTA IF the single goal of the email is to get people to book a call with Damian.

Image 2020 02 07 at 4.23.42 PM
One email, one CTA

2) Frame the meeting as a success meeting

We are predisposed to avoid salesy demos, the same way we turn away from the TV screen when the commercials start off. Nobody wakes up in the morning and says, “What a great day to buy a new software” after all.

To tackle this objection, frame your demos and meetings as customer success opportunities.

“Would you like me to help you and your team be more productive and save XX hours per month?”

“I’d like to show you how to put an end to the scattered email conversation. Let’s schedule a success meeting.”

“I’d really love to get you on a success call where we’ll set up your team, show you the ropes of HeySpace, and make sure we solve your biggest frustrations with team communication.”

Of course, this is not a sleazy way to trick your users into jumping on a call with you. Do your homework, research the user, and be ready to provide value.

Email #2: Follow-up

When: X days after signup

Screenshot 2020 02 25 at 5.33.11 PM

This email does some things well — looking for feedback and providing the next steps — but it needs improvement.

1) If you ask for more than one thing, break up the message into multiple emails.

Email is the new social media. People get a ton of broadcasts, promos, and automated sequences in their inbox. They scroll through, spending just a few seconds on each email.

You don’t expect people to watch a video, sign up for your product, and complete a survey out of a single post on your Facebook or Twitter page. (Unless you bribe them with an iPad, but that’s a different story). So it’s the same when it comes to your email communication.

HeySpace can easily break this follow-up into two emails:

Sending a separate email for the survey will also increase the Clickthrough Rate and eventually, the survey completion rate.

Note: Long-form emails have a place in the customer journey, but I wouldn’t use them for mission-critical onboarding emails.

2) Identify the most critical steps in your onboarding and help people to reach them.

We call these critical steps “value moment” because users experience critical value when they reach them.

Do everything humanly possible, so that your users reach the Value Moments before they forget your product.

Here’s your plan of action:

  1. Find the value moments.
  2. Eliminate any other distractions in the email onboarding.
  3. Provide the shortest path to success for your users, e.g. shortcuts to your value moments.

Instead of overwhelming the user with a list of all the features and things that they can do in HeySpace, they could list the 1 or 3 mission-critical things their user needs to complete in the app in order to become an active user.

Screenshot 2020 02 07 at 4.25.59 PM

For HeySpace, this potentially could mean guiding users to create their first board or to invite other team members.

This is how we do it with one of our customers:

For Veremark “Creating the first request” is a critical value moment, that’s why we use it as the only CTA to get the user back to the app and nudge them to complete the action:

Screenshot 2020 02 07 at 4.35.10 PM
Veremark value moment email

Notice how we don’t even mention any other features, how cool Veremark is, and all the other bells and whistles. Our goal is to get the user to submit their first request, that’s it!

We also address any possible objections like:

“It’s hard to send a request.”

“It takes a lot of time.”

”I don’t want to mess up something with my candidate.”

In some cases, all product actions are equally important, and there’s no clear order that they need to be completed in. In that case, framing the “next steps” as a customer success path/checklist is your best option. Here’s a great example from Dropbox:

onboarding checklist
Dropbox customer path onboarding email

3) Make your emails relevant.

It’s crucial that your onboarding emails follow the customer journey.

In the case of HeySpace, Asking someone to “Create a board” if they’ve already completed this action, would make your emails irrelevant.

Worse, once the user sees an irrelevant email, they start to perceive your whole email communication as irrelevant.

The goal here is to send the next most relevant action for the user:

If they’ve created a board but haven’t invited a team member, you want to ask them to Invite a team member in the email, and so on.

This is easier said than done. Setting up triggered emails based on the customer journey would require the technical setup of user events and careful planning.

Churn Email

For users last seen more than 10 days ago.

Screenshot 2020 02 26 at 10.40.30 AM
HeySpace churn email

I really dig this email, it’s awesome that HeySpace asks their inactive users for feedback.

Here are two ways to get better engagement on this email:

1) Send a follow-up to all users who haven’t responded.

I’d follow up this email with a second one to all people that haven’t replied. Doing this in Encharge is pretty straightforward:

  1. Send the first email →
  2. Filter users with “No reply received” →
  3. Send a follow-up email.
Screenshot 2020 02 26 at 10.45.04 AM
Increase response rate with a simple flow in Encharge

2) Increase response rate and automate the feedback gathering process with an inline survey.

No matter how many times you follow up, people are often just too lazy to reply to such emails.

Fortunately, we found a great way to get them to share why they’ve churned — we call it an inline email survey and it looks like this (taken from the Veremark onboarding):

Screenshot 2020 02 07 at 4.56.30 PM
Post-trial email survey

When a user clicks on a specific link, the answer is recorded in Encharge. Then, you can see the people segmented by the answer they’ve given (what link they’ve clicked).

This is how a segment of respondents looks like:

Screenshot 2020 02 07 at 4.59.00 PM
Respondents segments in Encharge

HeySpace could automate this even further. For example, if they answer/click “Price is too high”, they can send an automated email with a discount. If they answer “I didn’t understand how HeySpace work” they can send an automated internal notification to Damian to follow up with that person. Cool beans automation!

Money-making Tips 💵

With the emails out of the way, let’s see how we can improve the HeySpace onboarding, so they can make more 💵 without giving an arm and a leg.

1. Get users to experience the value of your product before asking them to upgrade.

And not the other way around.

HeySpace has a peculiar go-to-market strategy that combines both a freemium and a free trial onboarding model.

  1. A user signs up for HeySpace and they’re put on the low-level/freemium tier by default.
  2. Then, they’re asked to sign up for a 14-day free trial for the premium plan in order to lift the limitations of the freemium tier (like number of team members, file size, and so on.)
  3. If the user doesn’t convert within that window, they’re downgraded back to the freemium tier.

This model creates friction and a value barrier for the users.

Switching that onboarding process around — allowing freemium users to use the premium features for 14 days once they signup —  HeySpace can demonstrate value to a broader set of users and lock them in from the start:

  1. A user signs up for HeySpace, and they’re given access to a 14-day premium trial by default.
  2. If the user doesn’t upgrade within that window, they’re downgraded to the freemium model.

This go-to-market strategy can be fueled by the “loss aversion” effect to stress what people will lose if they don’t upgrade after the 14 days. Like, for example: “You currently have 5 members in your workspace. Your account will be downgraded on 24 Jan, and the following members will lose access.”

2. If you have a freemium model, aim to convert your free users quickly.

The general strategy we recommend for freemium products is: try to convert users as quickly as possible.

Send emails often and promote the tool aggressively from early on.

With a free trial model, people tend to wait until the end of the trial period to convert. 

It’s an analogy from the Parkinson’s Law that “work expands so as to fill the time available for its completion”. If you have a 14-day trial, people tend to widen their decision-making process to fill that window, if you have a 30-day trial, people would take 30 days, and so on.

Conversely, as freemium doesn’t have a timed window to experience the product, freemium users tend to convert faster than free trials. 

It’s your job to guide them to take that decision sooner than later.

As email expert Val Geisler says: “I tell all of my clients that with Freemium it’s a good idea to hit your new users early and often.”

MindMeister, a freemium mind-mapping tool, has leveraged this tip. I was recently using MindMeister and was prompted with this upgrade pop-up when I tried creating my 4th mindmap.

Screenshot 2020 02 26 at 11.32.17 AM
Upgrade Now prompt

They didn’t leave things there, though, and a few hours later I got this killer email in my inbox:

MindMeister upgrade email

This email does a few things great:

  • It’s sent at the right time. When I click on a premium feature in Mindmeister.
  • It uses scarcity to nudge me to upgrade.
  • It has a clear call to action “Upgrade now”.

HeySpace could easily trigger an email like this one with Encharge:

  1. When a user visits the HeySpace upgrade page ( or reaches the limits of the free plan (10 seats, tries to upload a file more than 5 MB). →
  2. Wait for 1-2 hours  →
  3. If the user hasn’t upgraded in that window  →
  4. Send an Upgrade now email.

This is how a flow that does this would look like in Encharge:

Screenshot 2020 02 26 at 11.45.02 AM
Trigger an upgrade email when a user opens an upgrade page or tries to use a premium feature. Easily achieved in Encharge.

3. Employ the “Better Life” email

The Better Life framework is a simple but powerful copywriting framework that:

  1. Emphasizes point A — the place where the customer is right now with all the pain that surrounds this place.
  2. Illustrates point B — a better life where the customer wants to be.
  3. Shows how your product is the bridge between points A and B.

When employing this framework with HeySpace can write an email that:

  1. Shows how teams are currently communicating. Stress the inefficiency/waste of time/challenges, etc. of that process as the gap between their current situation and a better life.
  2. Illustrates life after they cross the gap. How life could look like without the chaos of email communication and inefficient tools.
  3. Positions HeySpace as the right solution that can make team communication more efficient.

This is the Better-life email we wrote as a part of the Ve

Screenshot 2020 02 07 at 6.47.09 PM
Better Life email example

Want to get your email onboarding reviewed?

I’ve already dedicated a fair share of this blog’s space to big guys like Dropbox and Squarespace if you need of fleshed out and well-executed onboarding examples. This blog category is all about you — the early-stage SaaS companies.

If you have a SaaS company, want to increase your trial to paid conversion rate, and get your email onboarding reviewed in the same way, schedule a call with our team.

More resources on onboarding emails

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“Encharge helped us visually redesign our onboarding flow resulting in a 10% increase in our trial activation rate."

Camille Richon
Founder Payfacile
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