Blog - Email List Building and Growth

The Five Emails EVERY Saas and eCommerce Business Must Send

You’ve got the right product. You’ve attracted the right audience. You’ve even convinced them to sign up; giving you their email address. But what does it take to convert them to a paying customer?
Last month I spoke in London at the excellent Litmus Email Design Conference. They have just released the 20 minute video which you can find below. In this session, I share the actions a user must take (and the emails you must send) that lead to an AH-HA moment—the moment a user realises the value of your service, become hooked, and have no problem paying for that value.

The 5 Emails EVERY Saas and Ecommerce Business Must Send - Alan ORourke - The Email Design Conference 2015 from Alan O'Rourke on Vimeo.

Bonus: Download the five email worksheet
I have put toggether a handy worksheet to help you write all five emails. The worksheet covers what to write and when you should send each email. Download the worksheet (.pdf ) now:


Hello all and welcome!
My name is Alan. I’m the Director of Marketing for WorkCompass. It’s a B2B business that sells Performance Management software to HR departments of organizations that are big enough to have HR departments. You’ll be glad to know I’m not going to be telling you about this.
Instead, I’m going to focus on the 15 people that signed up to your service yesterday. We’ll also look at how you have just 30 days to convert them into customers before their interest runs out.

So, you’ve got 30 days to convert them to a paying customer – what will you do?

In my previous life, I had this very same problem – converting potentials into customers!
A few years back I founded an ESP (Email Service Provider) called Toddle, but I eventually sold it. I soon discovered that I was very good at attracting people to sign up; it was really easy. Usually, all I had to do was ask, and they would do it. However, there was just one problem; I wasn’t great at turning those people into customers.

Something was missing. We had a great product and a great team, but there was a piece missing from the puzzle.

I sold the business and moved on, but I still kept thinking about it. I was obviously missing out some vital steps – the steps that need to be taken before a user is converted into a customer.

So, when I sold Toddle I moved to research what everyone else was doing; I wanted to find out how they worked and how they were successful. I ended up signing up to hundreds of emails, different types of web services and even e-commerce sites. I wanted to see what it was they were doing. I tracked the progress and activity as they guided me through the process. As a result I was left with a lot of data, but from this data I could see some distinct patterns that had emerged from the process; it was a kind of a framework to build an activation campaign.

The Ah-ha Moment!

A user needs to take a certain number of steps that leads to an “Ah Ha” or “WOW” moment.
A few years ago with my design background, I would have tackled this problem from a ‘UX point of view’. I would have tried to optimize the application in an attempt to guide a user through the whole user-flow. But if people aren’t actually coming to the application, there’s a problem. So, this is why I needed to look to emails to drive this interaction and progress.

You’ve Got 30 Days To Activate The User…

To snag the user and convert them, you’ve got 30 days (a month) to do so. In these 30 days, you’ll need to be active yourself. Here are the 5 core emails that you need to send out to people to get them on board.

1. The Welcome Email

It’s quite straightforward. First impressions are very important and set the tone for the whole relationship. These impressions are likely to be one of the deciding factors as to whether a user will bother reading any future correspondence from you.

There’s a very fine line of getting that balance right – the balance of giving them the information they want without giving too much away. If you bombard them with too much information in the ‘welcome mail’, chances are they’re going to save it to read later, but as you’re already probably aware - no one ever reads their emails ‘later’. So, it’s a case of now or never.

This is an example from a Cliniko the Clinic Management SaaS product. They keep their ‘welcome mail’ very clean, simple and straight to the point. It basically tells you ‘Thanks for signing up’ with your login details and a few helpful tips as to how you can get started.

Asana, which is a project management tool, takes a different approach with its welcome emails. Its aim is to try and create excitement and curiosity through the design to get you pumped about using their product.

FogBugz is a bug tracking software. In its ‘welcome mail’ it tells you upfront what to expect over the course of the next 30 days: “Over the next 6 weeks, I’m going to send you exactly 3 emails. That’s it, I just want to help you learn a bit more about FogBugz”. It sets that expectation for the user right from the get go. They know they’re not going to be bombarded with countless emails and they’re probably going to look forward to receiving them when they do – their curiosity has been roused.

The email of course needs to contain important information such as user account information, how to get started and so on. Squarespace asks you to save it for reference later.

It’s very easy to forget in these ‘welcome emails’ how effective and personal they can be. A welcome from a team is nice, but a welcome from a person is even better. Whatever you do, please don’t send these from ‘no response’ or ‘please do not respond’ email addresses.

Bonus: Download the five email worksheet
I have put toggether a handy worksheet to help you write all five emails. The worksheet covers what to write and when you should send each email. Download the worksheet (.pdf ) now:

A clinic-booking site,, sends emails to their users via an Account Manager. Each email contains their actual picture and a signature. The people responding are ‘real’ people from the company. This is their way of trying to build a personal connection and rapport with their users.

The e-commerce site Shopify provides you with their Support Guru to try and help you get started. One global company, which I can’t really mention, has 400 million users, and every email comes from one woman called Liz, who doesn’t actually work in the company anymore. They haven’t gotten around to changing that, but there’s still a sense of a real person behind the emails trying to build some sort of connection.

Perhaps you don’t want to put a real person on your emails, and that’s fine. Sometimes people leave the company or maybe one person alone can’t be arranged. That doesn’t mean your welcome emails should lack personality. Take the company MOO for instance. All of their emails come from ‘Little Moo’, the company’s mascot (aka robot). This personal touch adds a little bit of fun, and this is what users want.

E-commerce sites’ ‘welcome emails’ are a little different. When they send their first welcome email, they usually include an offer, which I’ll go into more detail later.

2. The Mission email

The second email to think about often comes together with the first ‘welcome mail’. It’s often from the CEO, the Founder and it’s the ‘mission email’.

This is another opportunity for a personal outreach. It’s from a real person who’s trying to build that connection. However, it often has a second purpose and that’s to build a mission, to build a vision.

It’s an interesting technique – you might have read the book called ‘Made to stick’, which is about the power of stories in Marketing. This is exactly what it is. It creates a shared vision. It tries to state what the company does and where they want to take people. This is their way of telling you how they want to change the world. It’s a great tactic for getting people on your side. Instead of just them trying to sell something to you, it’s about you and them being on the same team and marching together towards their vision.

This email is a personal email from Denis my CEO in WorkCompass. It’s his personal story, and how he came around to creating his company. It tells you how he started off as an accountant and then how he got promoted to the Financial Controller, a Manager. It outlines how he had years of training as an accountant, but zero years of management training. It then goes on to tell you how within the first year he almost got fired because he was a terrible Manager, which then led him to create software to build a better management process to build a management framework.

In all honesty, the email’s really wordy, but in saying this, it’s also the most-read email in our sequences, and it’s the one that gets the most replies.

3. The Activation Email

The third email is the ‘activation email’. This is the email that pushes a user to the point where they’d see the real value of your product or service. This is often referred to as that ‘Wow’ or ‘Ah-Ha’ moment, and this is probably the most important email out of the five.

Twitter needs a user to follow 30 people before a user activates. This is the point where a user realizes the value and stick. This is Twitter’s core activation metric, and every email pushes the user towards this point. Facebook follows a similar route.

I’ve created a Twitter account, but I haven’t actually interacted with them. Last week I was looking back over all the emails that I’ve received from them trying to activate me. In the first year I got a 182 emails trying to activate me and push me towards this point. The following year, I got 400 emails. This is how important this metric is for them, and this is how much they are trying to push users towards it.
However, as you’re most likely aware – quality is better than quantity, and this is something that Twitter might need to reevaluate.

Dropbox’s core activation metric is to get users to install the Desktop app so all their initial emails push the user towards this.

I previously touched on e-commerce sites and their ‘welcome mail’. The key activation for an e-commerce site is that very first purchase. Once a user buys a product from an e-commerce store and the product is delivered on time this builds confidence and trust in the relationship. From this point, the user (the consumer) is activated, and they’re more likely to go back and shop with them in the future. E-commerce sites tend to push some kind of voucher, discount or sale, usually with a time limit from the very start to try and get the user to buy. They usually push this from the very start, because this is when the user is most engaged.

Activation is the critical link between user acquisition and revenue…

…This is one of the core points I was missing way back when I was running Toddle.

Finding Your Activation Point

Do you know what an activation point for your product or service is? Do you know how you can find it?

Ask your existing users these 3 questions:

  1. What would you do if you could no longer use this product/service?
  2. What was the primary benefit you received when using this product/service?
  3. Would you recommend this product/service to someone else? Why/why not?

Bonus: Download the five email worksheet
I have put toggether a handy worksheet to help you write all five emails. The worksheet covers what to write and when you should send each email. Download the worksheet (.pdf ) now:

Photo from the excellent photographer on the day: Rajesh Taylor

Sean Ellis of ‘Growth Hacker’ fame developed this method. He developed a series of questions with the tool, which is a free tool that allows you to drop a bit of a code onto your site to survey users. With these 3 questions, you can find out what the core value of your service is. This is not what you believe the core value is, but it’s what your customers think. It’s really interesting and helpful to look at the actual language they use and not the language that you use yourself, and from this, you can modify your activation emails accordingly.

Step by Step

It’s not always possible to demonstrate the activation in one step. Some products are a little bit more complicated and they need a few more steps. An example of this is MailChimp, which has a series of 9 emails. These emails guide you through the different steps of their product, which will get you to the point where you’ll realize “Oh, wow! This is great! I’m sending email newsletters”. It’s also a great excuse to keep in regular contact over that 30-day period to keep that relationship going with a user. In fact, I’ve noticed that MailChimp actually repeats this process a year later after you sign up. If you didn’t activate within the first year, they come back the following year and try again.

You probably have this content already from your support and sales teams. They’re asked questions from users all the time, so it should be pretty easy to pull this together.

Remember to push benefits, not features. For example, when Facebook pushes the feature of importing your contacts from Gmail, they push the benefit of ‘connecting with all of your friends’. Shopify works in a similar way by advocating the benefit of more sales and not focusing on putting a product up for sale.

Squarespace has put all its steps into one course, through an in-depth video, which they’ve pushed as their activation. Whereas Basecamp goes for a ‘one-on-one’ Webinar where you can actually interact with the Core Product or Core Marketing Team.

User Triggered Emails

Almost anyone can do what has been mentioned so far. Most of the ESPs have some kind of automation system, which allows you to automatically send a series of emails based on the time the user signs up. You’ll probably end up doing a bit of testing and playing around with regards to what is the best time and right sequence, but imagine how much more powerful it would it be if you could send an email to the user while they’re in front of your product at that very moment. Imagine knowing what they just did and being able to guide them with the next step…

You’re probably going to need some kind of engineering help to set this up and plug it into your existing product or service. Luckily, there are a few tools available such as that are making this process a whole lot easier.

Automate And Put Some Intelligence Into Your Activation Campaign

BugHerd is a company that provides bug-tracking software. Their activation is to get you to install a piece of code. They send out a whole series of emails pushing for this activation. Once installed, they’ll move you on to a separate sequence of emails – this is when they try to get you to use and engage with the product more. If this doesn’t happen after a certain period of time, they’ll send out a third sequence of emails trying to reengage you.

Tumblr also does something along these lines. Their emails are highlighted with what you have already done, so essentially, they’re trying to push you to the next step. Crossing out what the user has done is great for reinforcing user behavior, giving users a sense of completion and driving them to the next step.

Triggered emails open rates are up to four times higher than timed ones.

In e-commerce about 65% of people quit before they activate during the checkout process. E-commerce sites like use triggered emails to try and tempt the users back with Cart Abandonment emails. Once a user abandons the cart, send him or her a simple reminder to go back before the shopping cart expires. This is done by setting time limits, offering discounts, deals, and so on. These are all great examples of emails that you can send to lure your users to activate.

“Sending perfectly timed emails can result not just in an activated customer, but can increase sales by 15-30%!” - Direct Marketing Association.

4. The Last Chance

This is an email or a series of emails that are sent telling you your trial is about to expire. A common tactic used is – you’re about to lose data, you’re about to lose whatever you have invested in your trial so far. Microsoft, for example uses the message: “You’re about to lose data from your Microsoft Office trial”.

The fear of losing something is really a powerful motivator for driving user behavior.

The fear of losing something holds a much greater weight compared to gaining something.
So, this is a clever tactic worth utilizing in your final series of emails.

5. The Hail Mary Email

Normally, this is the end of the mail sequence, but there is one more type of email to consider – the ‘Hail Mary’. The 30-day trial is over, the user didn’t buy, but it’s worth trying to engage them again. For some users they just weren’t interested in your product at the time. For others, they didn’t have the time to trial it. This is your opportunity for one last hit - ask them if they want to extend their trial. You never know, they may just be interested in checking it out again.

Bonus: Download the five email worksheet
I have put toggether a handy worksheet to help you write all five emails. The worksheet covers what to write and when you should send each email. Download the worksheet (.pdf ) now:

SugarSync uses the ‘Hail Mary’ tactic by offering a discount. They might not have bought it the first time because of the price. If you’re still able to make money off your product or service by offering a better deal, do it. A lower price offer often will bring them back, but make sure you put a time limit on these offers, because this is a really good driver.

Another tactic is using this as a learning experience like FreshBooks and Zendesk do. They ask questions to try and figure out why people didn’t sign up during their trial. They obviously weren’t interested right from the start, so something must have been wrong, right?

Ask a user:

  1. Are you still interested?
  2. Was price an issue?
  3. Was the product too hard to use?
  4. Did you go to a competitor?
  5. Did the trial meet your needs?
  6. Was the trial too short?
  7. Or were you ever interested? Eg just doing research.

There is no downside to the ‘Hail, Mary’ email, there’s only a potential positive outcome.

30 days ago someone signed up to your service. You gave them a warm welcome, got them excited, and guided them step-by-step into finding value from your product. You have found out what the person needed, you gave it to them, and when they forgot, you gave them a gentle, or maybe a not so gentle, nudge. And you know something? You can automate all of these while you get on with the rest of your work.

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Now It’s Your Turn

I have put toggether a handy worksheet to help you write all five emails. The worksheet covers what to write and when you should send each email to convert users to customers.
Download the free worksheet now: