Email automation can be a powerful tool for your SaaS to boost new user activation and drive growth at every stage of the user journey, if used correctly.  

And that’s a big IF.

Simply flooding the inbox of someone that just signed up to try your product and sending them one email each day of the trial won’t help you increase your activation and conversion rates.

Your users’ mailboxes are already flooded with so much mail, it’s *really* hard to get through the noise.

So how do you do it right?

How do you use email automation to create value for your user?

You’ve guessed it ( or read it in the title), it’s using context to trigger emails.

Contextual email is more than simply segmenting your list of users based on demographics, job roles or location.

It’s about really trying to understand the user’s needs and create the best possible experience for them.

The problem your product solves might be the same for more than one user, but the path towards fixing the problem and seeing value in your product, will always be different.

It’s your responsibility to start personalizing the experiences you offer to your soon to be customers.

What you will find in this article:

  1. SaaS user journey stages overview( just to make sure we’re on the same page).
  2. The ingredients you need for your contextual email automation strategy: events, tags, scores, goals/milestones, JTBD and the ‘’magic powder’’
  3. The recipe: steps towards creating great CX with the help of contextual email automation.

SaaS user journey stages overview

When we talk about SaaS products, especially from a product-led perspective, the user journey stages look like this:

  • Awareness
  • Activation
  • Adoption
  • Retention
  • Advocacy

1 - user journey stages (1)


There are four stages of awareness, and you might interact with someone for the first time, in any of these stages. In order to properly package and deliver your message you need to understand what each of them are:

Unaware: when the users don’t even know they have a problem. You need to educate these users, not try to get them to try your product out. They will simply not understand why they should do that.

Problem-aware: the users recognise they have a problem. Maybe they are repeating a task each day that drives their productivity down and it’s starting to become frustrating. They are not ready to take action, they need to understand possible ways to fix the problem after clearly identifying the cause of their frustration.

Solution-aware: this is when the user identifies a few possible solutions for the problem. In the above example, these can be : hire an assistant, get a tool and automate it, eliminate the task altogether or replace it with something else by changing the process etc.

Product-aware: this is when they settled on one solution and also identified products they can buy. This is the step when they are looking to try your product and see if it’s a good fit.


User journey

The activation stage in the user journey is when someone subscribes to your trial, demo or free account. This is the user’s way of telling you that they are considering your product as a solution to their problem.

Unless you’ve raised false expectations and your product can’t deliver on the promise, now’s the time to properly put contextual email automation into action.

By sending triggered emails based on context, you will deliver a tailored experience for each user and guide them on the shortest path to their desired outcome.


This is when the user becomes your customer. The moment they decide to subscribe to your product.

You’d think your job is done now; invoice sent, money received, that’s all.

Well, wait a minute. I guess you want them to pay for the second month too, and third, and forth, and… see where I’m going with this?


You’ve managed to find someone that needs your product, got them to try it, showed them the value of it, and they became your customer.

This is where retention kicks in. You want them to become a repeat customer ( pay the second month too, at least).

I won’t tell you that retaining customers is actually cheaper than acquiring new customers, you’ve probably read it 1000 times by now.

But I will tell you that sending an email when the customer’s behaviour tells you they’re about to churn, can go a long way.


Happy customers become your advocates, if you treat them right.

Once they start advocating for your brand, you know you’re doing something right.

And as we all know, word of mouth is the best advertising there is.

If you can’t get users to the advocacy stage, you probably have a retention problem and should be looking into improving your product. Talk to your customers and find out how your product can better suit their needs.

Yes, you can use email automations for this.

The ingredients you need for your contextual email automation strategy

To properly plan and set up your email automation strategy you first need to get familiar with a few terms and understand their purpose.

Tip: knowing what you need will also help you find the best email automation tool for your needs, avoiding the unnecessary pain of setting up your account only to find out the platform doesn’t offer the right features.

Here is what you’ll need:

2 - Events, tags, scores, milestones


This is pretty much self explanatory.

Events are actions performed by the user inside your app. If you’ve ever used Google Analytics, I’m betting you are already tracking some events.

For SaaS users these events are small actions such as ‘logged in’, ‘updated a credit card’, ‘invited a coworker’, ‘created a project’, ‘added a task’ etc.

The events you need to track will always be specific to your product, even though some are common across all SaaS products.


Here is where things get a little confusing.

A tag is like a label that you apply to a contact’s information in your email list, based on a criterion selected by you, not what the user does. You can add and remove tags from a contact as many times as it’s relevant.

Tags help you segment your list so you can deliver a more personalized experience.

Here are some examples of tags you can use:

  • Track the journey stage: lead, PQL, paid user, trial user etc
  • Track behaviour: interacted with x campaign, visited pricing page x times in a week, downloaded ebook, opened chat support x times in the last 30 days  etc
  • Track in app engagement: invited a coworker, has connected x app, added a project, used x feature etc

Tip: events and tags can be confusing, I know. To separate them, think of the purpose you are tracking them for: use events to answer yes and no questions when it comes to a user’s actions and inactions that might determine whether to send an email or not.

Use tags to have a better view of your customers and be able to segment them into smaller lists (you might want to do a one time promotion campaign for a specific type of user; tags will tell you who they are and might also give you an idea of what that offer should be).

It’s ok to have “added a project’’ both as a tag and an event. It’ll make more sense once you start using them, I promise.


Tags are nice, but they lack scalability. This is where scores come into play.

Let’s say you want to create a list of your most loyal customers and reward them. Scores will help you  ‘’count/measure’’ the engagement that tags and events keep track of.

For example, you might start a campaign addressed to customers that have been with you for the past 12 months. The campaign objective is to convert them into brand advocates, so your emails will try to encourage referrals for example.

Every time the customer refers someone you can add 1 point to a score you name referral. Your campaign can then send more emails if the score stays below 5 for too long, or less emails and special bonuses if the score reaches 10 or 15 in a determined time.

The possibilities are endless, and the customer experience will be up to the roof.

Don’t get me wrong, you shouldn’t use scores just for tracking referrals: scores are great at every stage of the user journey.

Tip: scores can be negative too when you subtract points for inaction ( add 1 point for an action, subtract one for the inaction).  If you have a project management app and the user  score for “projects added’’ in a month is 10 and it suddenly drops to -5, it might be a sign they are about to churn and you need to engage them.

Goals/ milestones

Depending on the tools you use or the people you work with, you’ll either be familiar with goals or milestones, or use the terms interchangeably.

To be clear, when it comes to email marketing they pretty much mean the same thing. So as long as you are clear on what they represent, it doesn’t matter how you call them.

Goals/ milestones are the points in the journey you want your user to get to.

For example, a lead turning into a PQL ( product qualified lead) is an important milestone you want your user to achieve.

In order to get there, they might have to ‘’jump a few bridges’’ aka go through some steps/ actions that are specific to your product.

For some products it might be as simple as installing a tracking code or a browser extension without which your user would never be able to see the value of your product.

What’s the point of sending features and benefits email to a user that hasn’t even taken the first step?

Or worse, why should you send an email telling the user to install the tracking code, after they’ve already done that?

This is why we use goal tracking.

If a user performs an action or a series of actions, we should remove them from one automation and add them to another one that will guide them towards the next milestone in their journey.

JTBD – Jobs to be done

If events, scores, tags and milestones are more on the “technical’’ side of email automation- i.e they help you understand your user behaviour and trigger emails; jobs to be done can help you understand the user’s need or better said, the job they are trying to achieve, for which they “hire” your product to get it done.

Understanding JTBD will help you decide what’s the best journey for a specific user and what are the milestones they need to achieve in order to get that job done.

Here are some suggestions of most commonly used milestones, events, scores, tags, to get you started.

3 - Events, tags, scores, milestones examples

It’s time for the last ingredient.

The “secret sauce” that supports your email marketing automation

I have to admit there’s no recipe that will guarantee success, but switching from sequence email campaigns to a more contextual approach, can work like magic to your conversion rates.

Not to mention, it’s also more beneficial to your user.

What’s the point of sending an email like the one below, when the user hasn’t even logged in once since subscribing to the trial?

You should already know what “I managed to discover” and send me more relevant emails.


Gamification is nice, and can bring results. But the email above is just telling me about you and ignores my problem altogether. Sending an email telling me to try and hunt features instead of asking me why I haven’t logged in a second time, just doesn’t feel like you care.

But the right message at the right time is not the “secret sauce” I’m talking about.

It’s important to understand that no email campaign will work when it’s not synced with other tactics and tools that help your user succeed.

That being said, the magic comes when you optimise the in-app experiences too.

You see, email helps guide the user on the path to accomplishing their job, but if they log into your app  and see a blank screen and don’t know where to start, then you’ve lost them.

Right there, there’s no coming back.

No matter how many emails you send, how nice the design is or how good your copy skills are.

Contextual email marketing can only help make the experience better. But it’s powerless unless mixed with other tactics.

You need to optimise the entire user experience, and use your product as your main selling tool. By the way, empty states are not the only in-app optimization you should look into.

welcome screen

Source: Userpilot. Welcome Screens are a great way to segment your new users and thus personalize their onboarding flow both in-app and via email. Learn how to build them code free!

Tip: it’s scary when you are just starting out, not knowing where to begin and what emails to send. That’s ok, just think of the MVP concept. Contextual email automation can start small too. Try optimising the path between two milestones and grow from there. You don’t have to do it all at once.

You’ve got the ingredients, so far so good, what’s next you might ask.

It’s time to plan your contextual email campaigns and then start implementing them.

The recipe: steps towards creating great CX with the help of contextual email automation

In short, it goes like this:

  1. Choose the stage of the user journey you want to focus on
  2. Set a clear business objective and the KPIs that will measure success
  3. Focus on the user: what’s their most pressing JTBD
  4. Map the shortest path for getting that job done
  5. Define the events, tags and scores you will need
  6. Build the logic of your email automation
  7. Set it all up and test it

5 - email automation steps

Let’s take a closer look at each one.

Choose the stage of the user journey you want to focus on

What sets you up for guaranteed failure is wanting to fix everything at once.

It’s overwhelming and you’ll end up doing a poor job.

Before you start anything, look at your numbers and see where your conversion rates are suffering and could benefit from some email automation help.

If your SaaS is just starting out, look into optimising the adoption stage first. There’s no point in getting people to sign up for a trial if you have no guidance set up to help them. So start there.


If you’re on the growth stage, check out your conversion rates and decide where to focus first.

Are you seeing high churn rates? Start with retention.

Conversion to paid is good and retention is awesome? Maybe you want to look into ways of getting more users: this could mean a focus on the activation stage or even advocacy.

The important thing is to focus on one stage at a time and base your decision on facts and numbers.

Tip: where you need to start with is always going to be where your users struggle. You need to look at this from their perspective. Once you help them succeed, your business will too.

Set a clear business objective and the KPIs that will measure success of your email automation campaign

Once you’ve decided on the user journey stage you want to focus on, define a clear objective of what you are trying to achieve with email automation.

If you don’t know where you’re trying to get, how will you know you succeeded and most importantly, how will you know if you’re on the right track?

Start by stating the problem you identified in the previous step.

Are your adoption rates suffering because users need a lot of hand holding and your support team doesn’t have the means of guiding them in a time efficient manner?

This might be causing the users to simply give up.

If this is the problem you will be focusing on solving, state the objective as:

“Increase trial to paid conversion by x% and decrease support tickets by Y% through email automation”

This is just an example, the options here are limitless.

What’s important is that you make it very clear so you don’t lose focus and try to solve too many things at once.

Focus on the user: what’s their most pressing JTBD

You’ve identified the problem and set an objective, now it’s time to turn your attention towards the user.

What’s the actual job they are trying to solve with the help of your product?

Don’t forget, we’re still focusing on a specific stage of the journey and a specific problem you’ve identified in the previous step.

If the business problem was that your support team was overwhelmed, causing the user to feel lost and give up, look into where they struggle.

What are they asking your support team?

Usually when someone contacts support, they start by stating the problem: “I was trying to do x and can’t find/ don’t understand/ got stuck etc”

This is probably them stating the roadblock they encountered. Look a bit deeper and try to understand what’s the real outcome they are looking for. They might have an issue with installing a browser extension or not knowing how to use it. Or maybe they need technical assistance installing the js code. These are just surface level issues, what they are really trying to do is get more productive with their time, and your project management tool might help…if they ever manage to get set up. The lack of support is their pain, and you should be focusing on that.

Understanding the real job, the specific use case your user is hiring your product for, will determine the milestones you need to focus on.

Map the shortest path for getting that job done

Now that you understand the problem both from your business view and the user’s perspective, it’s time to map the ideal path.

Here’s where you’ll define the milestones your emails will help guide the user towards.

Keep in mind that these will need to be in a progressinve order: if milestone 1, 2, 3 and 4 were not reached, don’t guide the user towards milestone 5.

Reaching a milestone can mean triggering an event or a set of events. And the number of milestones simply depends on the product and the user journey.

Try and set milestones that are not too far apart from each other. This will make it easier to give more clear guidance and will make for a greater user experience.

Define the events, tags and scores you will need

It’s time to break those milestones down into events, tags and scores.

Not every email automation campaign will require you to use events, tags and scores together. Focus only on what’s needed for a specific campaign,in order to send personalized emails.

As mentioned before, your goal is to not sound like a robot, repeating the same messages to everyone.

What events, tags or scores do you need in order to deliver the right message at the right time?

Do you need to know when the user logs in? How often does it happen? Maybe how many times they’ve opened a support chat is relevant information?  

Write down everything that you might think it’s important, then you’ll start noticing patterns and you’ll simply know what you should be using.

Build the logic of your email automation

This is where it gets technical a bit.

Your automation needs to function in a logical way: if and when conditions are mostly used to trigger emails.

It’s contextual email marketing after all, right?

You might have some time based emails, but be careful with those. You want to always check conditions ( aka events, tags, scores) before sending a time-based email.

The entire journey can be built inside one automation or you can split it into multiple ones.

If you have more than 3 milestones, you might want to consider building a smaller automation to get the user from one point to the other, otherwise your campaign implementation will get messy and it will be harder to test and make sure you’re not missing something or aren’t making the experience a complete chaos for the end user.

Some email marketing automation platforms allow you to set “goals” inside a campaign, that can be used to move the user to a different point inside of the same campaign or start a new automation altogether, once the “goal” is reached.

Here’s an example: trigger emails in a linear path but interrupt it and bump the user further when they reach a milestone (some users might need 5 emails to get from point A to point B, others might only need one)

If you’re looking for inspiration, check out some ideas from ActiveCampaign’s automation recipes. I might be biased, but I find it to be a great tool for contextual email automation.

Set it all up and test it

There you have it, but before launching it, take some time to test it first.

Simply create a test account and check if your automation is triggered properly, then test each event, tag and score you used.

You want to make sure emails will be sent when intended.

Don’t forget to also test the experience:

  • Does the email display properly on mobile devices?
  • What about on a desktop browser?
  • Will it work both on a dark mode and light mode?
  • Is the font easy to read and big/small enough?

Looks hard?

Start small and expand your automations as you go, one email automation at a time.

Once you have one campaign set up, you should not only track and optimise it, but  start the process all over again and identify a different problem to focus on.

It’s a continuous process, but results will come fast if you don’t skip steps.

About the author

Adina Timar is a SaaS Product Marketer working with small businesses, focused on finding innovative ways to improve CX at every stage of the user journey. She’s the founder of AT-SaaS Marketing and the President of IAA YP Cluj Chapter ( International Advertising Association Young Professionals). You can get in touch with her on FB and Linkedin