Optimizing Onboarding Messaging for SaaS companies — An Interview with Alli Blum

Sofia Quintero
May 16, 2018 · 7 min read

In this interview with Alli Blum, Onboarding Optimization Consultant, we explore conversion copy and how to use customer feedback to optimize messaging for SaaS free trials. This interview is filled with practical advice and recommendations.

Sofia: Why don’t you tell me a little bit about your background and how you ended up doing this type of work?

Alli: My first few jobs were generalist roles that involved a lot of different kinds of writing. I ran a blog. I managed an ecommerce shop. I hired, onboarded, and managed interns. Along the way, I started to feel a drive to specialize. I wanted to build a business around solving a specific problem that multiple businesses faced, so I started talking to people. I interviewed somewhere between 40 and 50 folks to learn about the challenges they faced in their industries. Eventually, I learned that software businesses, in particular Software as a Service (SaaS) businesses, had very similar challenges from one business to the next.

What I discovered is that one of the most commonly neglected areas is new user onboarding, so that’s where I decided to specialize. When someone signs up for a SaaS product you have to show them what they need to do to be successful. When they leave, you have to help them come back to your product. And one way to help those customers get started is by sending onboarding emails.

The emails that are most effective are the ones that join the conversation happening in the readers’ heads in the moment when they sign up to start using a product while also showing them the one thing they need to do to get started. This kind of writing is called “conversion copywriting” and it’s based on deep research into how people use a product, why they start using it, and what they want to happen.

Now, I help companies keep more of their trial users by writing conversion-optimized onboarding emails.

Sofia: Can you take us through your process? How do you decide what messaging to use during the onboarding flow and when?

Alli: Before we even begin to think about what emails we might want to send, I guide companies through Onboarding Roadmapping Session where we consider three sets of questions.

First, I want to know how people are using a product. What do the people who become customers do differently during their trial compared with the people who don’t become customers? What leading indicators might we have about what behaviors lead trial users to upgrade?

The second area to explore is why people are here. Did they sign up because they’re curious? Because they’re trying to replace a tool they already use? Because their boss told them to vet new products? What outcome are customers looking for? How do they define success? How do they measure success? To answer these questions, I look at customer support tickets and at what people are saying about their problems on forums and review sites. After Roadmapping is complete I conduct several “jobs to be done” interviews with customers.

The last area we consider during Roadmapping is who “owns” onboarding. One of the reasons why onboarding is challenging for so many businesses is because onboarding touches every department. You need product, design, marketing, sales, customer support, customer success, and copywriting to work together. The biggest and most frequent challenge that my clients come across is that they have an army of customer support people but there’s no one from sales or marketing looking at customer data. Or the sales team is very concerned with spotting potential enterprise customers and so customer support teams are the only “sales” people that self-signup customers ever encounter.

Very often I find that teams take a “piecemeal” approach by shipping components of onboarding without anyone being in charge of the process, how success is measured, and what experiments they’re going to run, so a part of what we do at the beginning is to decide who is charge of onboarding.

Finally, after looking at user behavior, customer support tickets, and sorting through huge troves of what copywriters call “voice of customer data”, it’s time to plot onboarding email sequences and write emails to help people accomplish the task that they “hire” a product to do.

Sofia: How do you go about your initial research before working on onboarding copy? There are so many things to consider when it comes to designing great onboarding experiences.

Alli: Asking these questions is one thing. Actually looking at the data is another challenge altogether.

When I first started doing conversion copywriting, I’d get my transcripts and I would write things down on index cards. Then I’d lay them out on the floor and ask, “What are the big messages here and how do I put them together?” That wasn’t fun. And it’s even less fun when you have 30,000 rows of Excel data from a customer support export, because who wants 30,000 index cards? I started using Airstory, a writing software, and it was so much easier to create the cards from transcripts and to organize the messages that I could find manually in an export from Zendesk or Drift — but it was still a pain to trudge through customer support tickets in a spreadsheet.

I was looking for a tool that would be able to take an Excel spreadsheet and make it readable and that was the first time I used EnjoyHQ. When I imported a spreadsheet, it was like magic. I can quickly see all the questions and comments that people made in an easy-to-read ticket format instead of squinting at a tiny clipped spreadsheet cell. Instead of running searches over and over with an “edit, find”, and then copying and pasting the data, I can run a search for a feature might be talking about and see all of the tickets come up one by one.

With EnjoyHQ, I don’t even have to worry about massive spreadsheets anymore because I can pull in data from customer support tools with integrations. Being able to see everything in one place and being able to search through it with the option of viewing suggestions of things that might be relevant, is really, really helpful because a lot of times things that may be relevant — different types of customer data, different things people are saying — may not have the same terms or phrases and I may not be able to find them manually.

Sofia: What would be your advice for someone currently working on their onboarding messaging? What are the things you noticed would make for a better onboarding if people did them more often?

Alli: The first piece of advice is about getting into the right mindset. Almost all of my clients will say, “We have so many great features and we built them all because people asked for them. If we could get more people to use all the features during their trial, maybe more people would upgrade to become customers.” I remind people that no one’s here for your features. They’re here to solve a problem.

Instead of having a mindset of, “How do I show people everything in my product?”, have a mindset of, “How do I get people started? How do I help people navigate a world that they are new to? What does somebody need to know when they know nothing about how my software works or how it can help them?”

Once you have that mindset, instead of thinking about onboarding as this scarily complex problem of “How do I do the behavioral triggers for my email sequences?”, you can say, “How do I help people get started? What information do I need to share with them (and when) so that they can solve the problems they have when they sign up to try my product?”

If you know what people need when they sign up you can help them figure out whatever problems they have. That’s my number one piece of advice.

The other piece of advice to put one and only one call to action in each email. In copywriting we call this ‘the rule of one’. It states that you write every piece of copy for one reader, you give them one offer, you invite them to complete one action, and offer them one way forward. Instead of sending an email that says, “Here is the 22-minute video or the 35-page guide to our product. You just need to read it all and you’ll be good to go,” say, “Here’s the one thing you need to do to get started”.

Whatever that one thing is that people must do, start with that as the first task you’d like people to complete. There’s a slight caveat that you can have different versions of the call to action. If you have complex software, you can say, “Go do this thing,” or you can say, “Watch a video or read an article about this thing,” but you want to confine each email to one big idea.

Sofia: Alli, where can we learn more about your work?

Alli: My website is a good place to start, AlliBlum.com. I write about what I have learned and all things onboarding including a quick free intro course to SaaS trial optimization.

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