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February 12, 2021

Behavior-Driven Customer Messaging for SaaS Three Blueprints You Can Use

By Aggelos Mouzakitis

How can you create behavior-driven customer messaging for your SaaS company? This is the question on everybody’s lips.

In a previous interview with Jane Portman, she shared with us the most important events we need to take into consideration when emailing our customers. But what exactly should we send? In this interview with Jane Portman, co-founder at Userlist, we dug deeper into exactly what you need to send and what specific campaigns you need to have running.

Jane Portman is a UI/UX consultant specializing in web application design, co-founder of Userlist, and host of UI Breakfast Podcast. At Userlist, Jane’s goal is to provide flawless UX and help users be awesome at their customer messaging.

By the end of this article, you will know exactly what to send, when to send it and how it needs to look, how to segment your campaigns according to users’ product maturity, and how to convert more free users with the right timely emails

Today, we’re going to talk about actual business examples. In our previous conversation, we were discussing what kind of events and properties you can be tracking in your SaaS business. “Userlist is a customer messaging tool for SaaS and like any other SaaS business, we are also struggling with onboarding and definitely paying a lot of attention to it,” Jane told us.

As Jane explained, “One of the challenges that our potential customers face is that before you even draft your first message, you need to understand and plan a few important things. The number one thing you need to do is translate your customer success into the language of properties and segments. And sometimes it’s obvious sometimes not so much. And second, you need to figure out the right time when you can be sending helpful messages and this all really goes hand in hand”.

“It’s wonderful to plan together what you’ll be tracking and what you’ll be sending. In our conversation today. We will walk through three business examples and different setups that might be helpful in your particular business. Blueprint number one today is helping users overcome a technical challenge. Essentially, when your product is somewhat tech-heavy and you need to offer your hand during onboarding.”


Understanding The Purpose & Benefits Of User Segmentation

She continued, “Here is Dave a founder of DevHunch. It’s all imaginary, but we decided to make them with faces so that you can imagine that this is a real person. It’s a product user tool for developers. They’re bootstrapped and profitable. And Dave really doesn’t have too much time to onboard each of the users manually, however, he would love to offer help. So, here’s how he combines these approaches in his onboarding sequence.”


“Let’s see what success looks like for their users. They know that in order to be successful, they need to do have at least one successful integration. They need to configure their first project and they need to invite at least one team member. In order to be able to track all of these, you can see that Dave has three properties: integrations, projects, and team members,” Jane told us.

According to Jane, these are just numerals. “Typically, there’s zero and everything is just getting started. And when they turn into one or more, you can understand that something’s been going on and the product is being adopted successfully. He also has a segment called activated users, which has all three of these conditions together. When the user joins the segment activated users, that means that all of these conditions have been performed successfully and they are already on board with the project.”


Structuring An Onboarding Campaign

Let’s take a look at the onboarding campaign. It’s time-based but it’s smart, which means that it’s not sent automatically to everyone. The key here is that Dave uses behavior data for keeping messages, not for triggering them. Therefore, he decides a sequence when these messages are going to be sent, but skips them.

“He has a campaign which is called basic onboarding. It starts when the user creates an account and we can see the sequence of messages here. The first one is the universal welcome message sent to everyone. And then you can see three messages sent within one or two days. In an ideal situation, if the user is really up to speed already, they’ll get just the welcome email. And that’s perfect because they are ready to move on with your product.”

As Jane told us, “They don’t need your activation emails. And another thing that Dave is doing with his email automation is now nurturing. He is advancing users. We’ve already described the segment called activated users, which means that all three conditions have been applied. Once the user joins the segment, once they’re activated, they’re moved into the educational stage where they are sent weekly productivity tips. These tips will never be sent to someone who’s struggling to get on board, they will be sent to those who can make good use of them.”

“Once the user becomes activated after seven days, they will get their products, your tip number one, productivity tip number two, number three, and so on. You can actually be using some additional properties. Blueprint number two, dealing with advanced features, meet Joanna, head of marketing at, which is an online photo editing tool. And generally speaking, it’s a pretty straightforward application.”


Educational Sequences For Advanced Features

As Jane explained, “Typically, users don’t need an educational sequence to get onboard. They can figure it out pretty well, but their complexity is that some areas of the product are harder to master. For example, in our case, that’s a batch photo editing or print management. In order to track these, we have events happening for a user batch editing started and print started.”

Jane continued, “And when these events appear in the user timeline, we can understand that the users are making use of these features so we can start bringing them on board and give them additional education about these topics. John is sending smart educational campaigns. One is for batch editing before his custom event batch editing started, they started getting educated.”

“We’re keeping their inbox clean of clutter and being respectful by only sending highly relevant information. In addition to that, she also sends webinars and things like that to people who use certain features a lot. She has a custom segment for the power users.”

“She only has a customer segment for advanced users of batch editing. These are users who have used this feature at least five times over the last month and advanced users of printing who have used this at least five times over the last month. She doesn’t send the webinar announcement to their entire user base. She only sends it to users who have actually been using specific features lately, Jane told us.”

Dealing With The Freemium Model

Blueprint number three is about dealing with freemium. Framing is always a challenge because you don’t have a specific deadline for converting people. You can’t do it all of the time. It’s almost like beating a dead horse and trying to make them convert. Jamie is the founder of Simple Tracker, which is a time tracking app and they have a freemium offering

As Jane explained to us, “The vast majority of their users are on the free plan and he wants to automate those conversions. What does success look like for their users? In order to be effectively nudging users, we will be nudging only those who are actually getting value from the app. Jamie understands whether this user belongs to the paying segment or to the freemium segment.”

“Let’s see how that’s applied in this case. Segments are really useful. One segment is called free users and when the billing state equals free, the other is paying users when the billing state equals active and the last one is active users. These are people who have, before a meeting, logged at least five times over the last six days. In this case, you can see again how separating by putting conditions into segments gets really handy.”

“When you start applying campaigns later on, you don’t have to worry about the definitions of these segments. You just know these are free users, this is a pain, and you only have to set up those conditions once in the segments, part of your app. This is how segments look in a user list, for example, but that can be slightly different in your tool of choice.”

“Here’s a campaign that Jamie uses to nudge their active users into pain. The campaign name is upgrade nudges. The trigger is when the user joins the segment active users. So we are triggering just that narrow segment of people. This campaign stops when the user joins the segment paying users.”


Final Thoughts

We hope that this article has helped you to learn more about behavior-driven SaaS messaging and how it can enhance your product’s customer journey process. It was an absolute pleasure to speak with Jane Portman again about such an important topic. There is plenty of value to be extracted from her insights on behavior-driven SaaS messaging. 

Aggelos Mouzakitis

Aggelos is the founder and Growth Product Manager of Growth Sandwich. He is among the first Customer-led experts in the world, leveraging advanced, Jobs-to-be-done customer research to orchestrate and guide Growth for B2B SaaS companies. A- and B- series SaaS are hiring him to organise, design and execute programs that infuse the whole company with qualitative data, empathy and the necessary knowledge to address any growth dilemma. In the last 4 years, he has worked with more than 100 SaaS companies and trained literally, thousands through my physical and online courses.