5 step playbook for creating tailored user onboarding experiences

Why tailored onboarding matters

User onboarding is critically important to tech businesses. Improving onboarding is one of the best ways to drive retention and is a key driver of a product-led business. Even incremental improvements have an outsized impact on the business.

The most effective onboarding strategy is tailoring the experience based on user needs. We saw tons of success with it at Dropbox and since starting Dopt I’ve spoken with many other leading companies, like Postman and Airtable, that have had similar results.

Tailoring our onboarding was one of the most successful experiments we ran in the last year and drove a huge 10% increase in team activation.

If tailored onboarding is proven to work, why don’t more teams do it? Well, it’s hard. Teams wrestle with the questions: How should I segment my users? How do I leverage customer data? What should the experience be? How can I create a great experience without being intrusive or boring? How much dev effort will this take? How will I know if it’s working?

B2B SaaS products are super complex. To be successful they have to help users through integration-and-data-heavy setups and deliver value to a variety of users.

This complexity is what makes building tailored onboarding hard. But it’s also exactly the reason tailored onboarding is effective! With tailored onboarding, you can cut through the complexity of your product to help users reach their unique goals.

Even the simplest approaches to tailoring onboarding can lead to huge wins. One of our biggest wins at Dropbox was asking users what they wanted to do with the app and then connecting them with that value.

You can take an approach like this earlier than most think. Teams should start investing in tailored onboarding after their initial MVP when the value of the product has been validated. By starting early and simple, you’ll get good results and will set yourself up to learn as you grow and things get more complex.

5 step playbook for creating tailored onboarding

While there’s not a one-size-fits-all onboarding experience for B2B SaaS companies, there is a playbook to get started on creating one that’s right for your unique users, product, and business model.

Here are the steps:

Let’s break these down 👇

1. Understand your users and what they’re trying to accomplish

The job of a growth team is to connect users with the value your product offers. At the core, this means understanding your users. What are their biggest problems? And what do they intend to do with your product to solve those problems? The best framework for thinking about what users are trying to accomplish is jobs-to-be-done (JBTD).

This framework will help you and your team be grounded in user needs. For example, some of the key Jobs for Dropbox users are “backing up files”, “sharing photos”, and “collaborating with coworkers”.

How to learn your users' JTBD

The best way to know your user’s JTBD is to simply ask them! Start with a simple open-ended survey question: “What are you trying to accomplish with [product]”? Scaled research platforms like Sprig make this easy, but ad-hoc emails or remote user studies work just fine too. After a few weeks of getting answers, you should start seeing patterns of what your users expect to achieve by using your product.

Next, combine the qualitative learnings with other sources of data like analytics and demographic data from a CRM or LinkedIn. This work will help you understand if different types of users using your product have different JTBDs. These are your user segments.

Common user segments in B2B SaaS

The complexity of B2B SaaS makes segmentation challenging. Here are some of the most common examples of segments we’ve heard to help you brainstorm what might work for you:

Segment	Examples	Thoughts
Plan or SKU	Free trial, Plus, Pro, Enterprise, Add-ons	The most basic segment in B2B SaaS.
Lifecycle	Onboarding, Activated, Highly Engaged, Dormant	Onboarding is only one stage of the user lifecycle.
JTBD or usecase	Product specific. At Dropbox, these could be “storing files”, “sharing photos”, or “collaborating with coworkers”.	This is one of the most underutilized segmentation strategies.
Functional Role	Sales, Marketing, Developer	Common, but a potential trap. It may be a better strategy to segment on JTBD because often different roles will have the same JTBD.
Collaborative Role	Creator, Collaborator, Viewer, Invitee, Team Creator, Team Joiner	Common for productivity and collaborative products. The concept of a team or org can be powerful here.
Nth user	1st user, Nth user.	B2B SaaS apps often require setup that’s unique to the first user. That first user is also usually an admin (whether they intended to be or not).
Source	Specific landing page, general sign up.	Usually very effective.

Tailoring onboarding by plan or SKU is a good idea because you’ll want to connect users to the different values your products offer. It’s a great place to start, but we’ve heard from our research that almost all teams want to segment beyond plan and SKU. We agree, we think that’s where some of the biggest opportunities exist.

For example, Airtable tailors their onboarding based on JTBD and Nth users.

If someone discovers their use case via an Airtable landing page or template, then it's important that we connect them with that value by tailoring their onboarding to the same JTBD. Similarly, a user building their first workflow for personal use has meaningfully different needs than the 5000th user joining Airtable at a large enterprise.

As another example, Postman tailors their onboarding based on Collaborative Roles.

We segmented our onboarding based on if the user was the team creator, an existing user joining a team, or a new user joining a team. This enabled us to tailor the experience and language to the most important actions and connect each user to the relevant value.

2. Map out their end to end onboarding journey

Now that you know who your users are and what their key JTBD is, you’ll want to know what their end-to-end onboarding journey looks like. This will help you stay grounded in the ultimate goal of onboarding - to connect users to the value they’re looking for.

Mapping end to end journey and aha moments

Here are the steps to creating an end-to-end user journey:

Here are some good resources to get you started: Unusual Ventures has my favorite high-level B2B user journey you could use for framing and identifying the step -1, Reforge popularized the set up → aha! moment → habit loop framework, and Atlassian has my favorite activity to create a journey map.

To really go deep, create a journey map with actual product screenshots of each step. It’s eye-opening because you’ll see the problems and opportunities very tangibly. That’s how many steps there are?? Step 3 doesn’t make any sense! It’s a simple and powerful way to get insights and build alignment.

3. Use data to power the tailored experience

Okay, now for the data. To develop tailored onboarding you’ll need user, company, or application data to create the segmentation conditions, such as usecase = upload photos and integrations_set_up = 0.

Create a data plan

Look back at your end-to-end journey and take inventory of what pieces of data you need to achieve your onboarding steps from #2. Figure out if you have the data already or whether you need to start capturing it.

If your customer data isn’t super usable, don’t wait until it’s clean to get started on your onboarding. Try tailoring on just one property! You’ll still be able to make an effective tailored onboarding.

Types of customer data

To help you think about what data you might need, you can think of two types:

Generated data: data that is generated or enriched as a user uses your product. e.g. user props and events like signed_up_date, org props like number_of_integrations, or other props like a landing_page they arrived from.

Captured data: data you ask users for. e.g. survey responses during sign-up like usecase = sharing photos or role = marketing.

The easiest way to tailor onboarding using data

Like I said before, simply asking your users what they hope to achieve with your product is the most straightforward way to tailor onboarding.

For example, help users whose usecase = upload photos more easily upload photos by focusing the onboarding experience towards achieving that JTBD.

This isn’t a silver bullet, but it’s probably your best bet. At Dropbox, we implemented this strategy on our mobile app and it was extremely effective. Wistia found it effective too. Hubspot tried it and ultimately ended up ripping theirs out, but still learned critical insights from it. If there’s a place to start, it’s this.

Principles for quality survey experiences

I’m sure you don’t like entering your information into a sign-up form. Neither do your users. Sign-up surveys often create unnecessary friction and give no value back to users. Here are some simple principles to create quality survey experiences:

4. Design and develop the onboarding experiences

Okay, now you have user segments, their JTBD, their end-to-end onboarding journey, and data to tailor the experience 🎉. The next step is to design and develop the tailored onboarding experiences.

Of all the steps in this playbook, this might be the hardest. It’s worth calling out that “no onboarding is the best onboarding” is a fallacy. Of course, you should always be striving for quality design of the core product, but even with the best information architecture, discoverability, and usability, users will still need help discovering and understanding how your product can be valuable for them.

Principles for quality tailored onboarding experiences

To help with creating quality tailored onboarding experiences, here are some principles:

To help with creating quality tailored onboarding experiences, here are some principles:

Products that help you create onboarding

Developing onboarding experiences that follow these principles is hard. There are tons of products on the market that help teams create onboarding, but none of them are built for engineering, product, and design teams. They’re brittle, they cut engineers out of the process, and they offer a limited set of UI modalities.

We started Dopt to give product, engineering, and growth teams tools to more easily develop tailored onboarding experiences that are fully integrated, work with their UI components, and fit into their product development workflow.

Inspiration for onboarding experiences

You can take inspiration from other best-of-breed onboarding. I highly recommend you check out pageflows.com. It requires a subscription, but it’s worth it. Some of my favorites are Miro, Hubspot, and Superhuman. Growth.design is also great for tear-downs and design principles, but they aren’t as focused on B2B.

5. Launch, learn, and iterate

Start small and iterate

If you’re a growth team, you want to iterate fast to keep learning, so start small. From this playbook, the minimum steps to get started are:

Partner with research, learn from your users

I can’t overstate how important user research is to this process. The entire first step of the playbook is actually just research! If you have a research team, form a strong partnership. If you don’t, prepare to learn the basics 🙂. In addition to using research to discover your users’ JTBD, also run evaluative tests of your onboarding prototypes before you ship them. At Dropbox, this was a critical part of our growth practice and resulted in significantly better experiences for our first iteration.

Measuring onboarding and activation

Measuring and benchmarking activation is hard because every product has a unique definition of activation (like Slack’s 2,000 messages metric). Here’s a useful playbook for creating your activation metric. The most important part of measuring activation is not getting lost in the weeds of complex modeling and making sure that onboarding and activation drive retention.

At the end of the day, onboarding and activation exist in service of setting up users for long-term retention. As a result, a great activation metric should represent meaningful progress and habit-building that correlates with that retention. If your activation metric suggests that 75% of your new users are activating, then the metric you've chosen is probably not sufficiently correlated with long-term success.

Takeaways

And there you have it: how to create tailored onboarding experiences. It might feel like a lot, but we hope this playbook will give you some clear steps and examples to get started. Onboarding is one of the most challenging product and design problems, but also one of the most rewarding to get right. It has a huge impact on the user experience and plays a critical role in driving product-led businesses as a whole. Go forth and onboard!

Thanks to Lauryn Isford, Jesse Miller, Sandhya Hegde, Ian Taylor, Alon Bartur, and Alex Chan for giving feedback on drafts of this post.

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Dopt beta

We started Dopt to make it easier to build fully integrated tailored onboarding into your product. We provide powerful building blocks to define targeting and flow logic. Our APIs and SDKs give you full control over the UX and fit into your product development workflow, saving valuable dev time.

We're working with a small group of design partners as we build Dopt. If you’re creating tailored onboarding and our approach is compelling, we'd love to hear from you.

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