How to Build Your SaaS Onboarding Strategy

To improve your SaaS trial to paid conversion rate, you're best off starting with a strategy to onboard trials instead of implementing random tactics. This article walks you through how to create your strategy.

Do I need a Strategy? Why can’t I just improve my UX?

Let’s get something out of the way - Onboarding UX walkthroughs are valuable (I certainly do them!)

These walkthroughs identify surface problems that will likely improve conversion (or are worth experimenting with). But a review is ultimately tactical and should support a plan. Doing a review without looking at the bigger picture makes it likely you’ll be optimizing for a local maximum.

Here’s a basic example, imagine you’re running a business with two types of users - dev managers and devs. Dev managers are the buyers and devs are the users. You could have literally the best UX possible for onboarding devs… but if the dev managers can’t figure out what they’re buying and why they should buy, you’ll be leaving a LOT of money on the table.

What is an onboarding strategy?

Your onboarding strategy identifies three things:

  1. Which customer segments to focus on converting (and why)
  2. The outcomes your trial signups want to get from your product
  3. How to change the experience so trials in those segments get the outcome they want

1. Which customer segment(s) to focus on, and why

This is one of the most important questions to answer, because it helps you understand the reason your prospects sign up for your service. This is part of your positioning, and I strongly recommend reading April Dunford’s book on positioning called Obviously Awesome if you’re trying to figure out WHO your key customer segments are.

2. The outcomes your trial signups want to get from your product

Also known as “which jobs are your customer hiring your product to do” (e.g. Jobs to Be Done) or “what’s your customer’s desired outcome”, onboarding success might look different to your different segments.

Imagine an email marketing tool that’s used by three different types of customers: SaaS founders, ECommerce companies, and Content Creators:

  • SaaS Founders might want to send events to the tool and then send emails to customers when events did (or did not) happen
  • E-Commerce companies might want to slurp in data from Shopify and set up Abandon Cart and Winback emails
  • Content creators might want to integrate a lead capture popup into their blog / website

In a pre-product market fit company you’re better off with a generalized approach to onboarding until you know who your most valuable segments are.

In a scaling company you have a better idea who your key segments are. At this stage factors like (but not limited to) market size, lifetime value, business strategy, competition, and a host of others will help determine the segment(s) to optimize for.

Understanding what success looks like to each segment will point the way to helping your new signups get to a happy place with your service.

3. How to change the experience so trials in those segments get the outcome they want

Once you understand who you’re selling to and what success looks like to them, you’ll have a good high-level understanding of the kinds of things to change to help your prospects succeed.

For example, imagine you’re running our email marketing tool and learned that your most valuable segment are bloggers. A Blogger’s main goal might be to collect emails from site visitors in exchange for a free PDF. In that case you might decide to make it as easy as possible to install a popup email collection widget that would deliver a PDF to people who signed up.

But if you sold to Youtubers and few of them had websites, you might focus on helping them set up landing pages for each video they produce to collect email addresses and send email signups a drip sequence.

How to build your onboarding strategy

To figure out answers to the above questions, you can rely on two types of data.

1. Product Usage Data

Digging through the data can yield insights about areas of opportunity to invest in. For example:

  • Do people onboard on a mobile device or desktop? Should we invest in improving one experience more than the other? How should they be different (if at all?)
  • What does feature usage look like in active vs. churned customers and converted vs. unconverted trials? And how should we structure onboarding accordingly (read more about how I did this successfully in How we reduced churn by 87.5%).

When you have enough data, you’ll understand what your successful customers do and what your unsuccessful ones don’t do.

For example, former Twitter PM Josh Elman says about Twitter

Once a user follows 30 people, they’re more or less active forever.

Just think about what you’d do if you knew that about your app. I stumbled on the same approach back in 2012 and have been using it ever since… because it works.

2. Qualitative Data

There are three primary sources of qualitative data that can help inform strategy.

1. Session Recording tools. Installing tools like Full Story or SmartLook are magic. They can help you understand how people in different segments use your app (and where your experience is falling over). In recent memory watching user sessions helped me:

  • Understand why signups had cratered, and formulate a hypothesis as to why (we had changed pricing recently and raised it substantially for a few customer personas. When people hit the new pricing page they realized pricing ramped quickly based on specific usage patterns that we hadn’t considered, and would bounce.)

  • We were using an onboarding checklist. The checkboxes weren’t clickable but looked like they were, so people tried to click them. This frustrated users at a key point in their lifecycle when we wanted them to succeed with joy, not feel like they were failing with frustration.

  • I was working on an app where people got lost in a multi-step onboarding process, didn’t get value, and eventually bounced. Full Story helped me understand where the leaks were and how to tighten up the process so more people could succeed sooner.

10/10 would use session recording tools again.

2. Phone Calls. Hopping on the phone with your users can yield huge insights. You’ll want to talk to:

  • new trials to understand what problem they were hoping your app would solve
  • trials who didn’t convert to understand why your app didn’t meet their needs
  • recently converted trials to understand why they converted
  • active customers to understand the value they get

Basically you need to figure out:

  1. For new trials, what value do customers expect? (So you can give it to them)
  2. Why did prospects not convert? (If they’re in your ideal segment, you need to address the problems they have.)
  3. Why did prospects convert? (So you can help more people have the experience these folks had.)
  4. Why do customers stay on board with you? (So you can help converted prospects continue to get on-going value.)

3. Customer Feedback. It can pay off handsomely to ask for feedback when customers sign up, when they convert, and when they don’t convert. Putting this feedback into a user feedback tool ensures you’ll have it at hand when you need it. Reviewing it along with help desk tickets from trials and newly-converted customers can provide helpful insight about how to improve the customer experience so more people convert.

Putting your Strategy into Action

Once you’ve identified:

  1. which customer segment to focus on and why
  2. what success looks like to them, and
  3. what to change about the experience to help them succeed

…and you’ve grounded your strategy in data, you’re in a great place to actually make a list of onboarding experiments to increase conversion.

At this point I bucket changes into several types:

  1. UX changes we should make
  2. UX changes to experiment with
  3. Supporting onboarding tactics

1. UX changes we should make

Pretty clear - these are changes we’ll definitely make. They’re foundational enough to the strategy that they need to be done.

2. UX changes to experiment with

These are changes you think may yield gains. You can prototype these on sites like, builds Buttons no Nowhere, A/B test them in production (if you have enough traffic), or implement them to watch how they’re received and make a judgement call on whether to keep them or discard them.

3. Supporting onboarding tactics

There’s a whole host of these that can help improve onboarding. My go-to’s are:

  1. Welcome videos sent from tools like Bonjoro and BombBomb
  2. In-app guides like those provided by AppCues
  3. In-app chat like Help Scout’s Beacon and Crisp
  4. Automated onboarding emails from companies like Vero and UserList

Once you’ve got a strategy, know what changes to make, and have identified supporting tactics to help improve conversion, it’s all about execution and learning which changes move the needle and which don’t.

Improve your trial to paid conversion

Get two articles per month to improve your onboarding and trial to paid conversion. Subscribe for the next one.

Max 2 emails per month. Unsub anytime.