Have you ever had a customer sign up for your product, receive the initial welcome gift, and then... do absolutely nothing? It’s a common frustration in the B2B world. 

We spend so much energy getting them to the point of purchase, only to watch them fall into a post-purchase pit of despair where doubt and overwhelm take over. 

In fact, change is hard even when it’s good, and without a clear path, your customers might just decide that doing nothing is easier than figuring out your software.

In this article, you'll discover how to build an onboarding program that wins both hearts and minds. We’ll cover how to set measurable goals tied to customer value, how to segment your audience without losing your mind, and the best channels to guide users toward their first "aha!" moment. 

Defining onboarding beyond the checklist

Onboarding isn't just a technical to-do list; it's the process of leading customers on the path to value and bringing them into your community. 

When we talk about onboarding, we're really trying to accomplish two distinct things:

  1. Product adoption: These are the nuts and bolts. The user needs to log in, click the right buttons, and set up the features required for basic functionality.
  2. Winning hearts and minds: We need to make the customer feel great about their decision. They’ve made a big commitment, and we need to validate that they haven't made an expensive mistake.

It’s important to remember that you aren't talking to a logo or a company. You're talking to a person (or a small group of people). The more you recognize that you’re a person talking to another person – not a corporate entity – the more your messaging will resonate.

The Tuckman model and the pit of despair

In business school, we often learn the Tuckman model (forming, storming, norming, and performing) regarding team growth. It applies perfectly to onboarding too.

Right after purchase, customers are excited. But then they hit the "storming" phase: What if this doesn't work? What if I look bad in front of my boss? Onboarding acts as the bridge over this pit. While we might not stop them from feeling a little nervous, we can grab them as fast as possible and move them toward confidence.

Building a foundation with goals and alignment

You can't build a successful program if you don't know what you're aiming for. When picking your onboarding goals, follow two rules: it must be tied to customer value, and it must be measurable.

A goal shouldn't just be something that's "good for the company." For example, when I was at Fivetran, we found that when a customer connected three data sources, they suddenly saw the power of the tool. It was a moment for them. Because we could count it, it became a perfect metric to align the whole organization around.

Start small with segmentation

It's tempting to create 250 different segments for every possible use case, but unless you have a massive team, you won't be able to manage that. Start with the big differences. 

At WordPress VIP, we start with two main groups:

  • Technical users: They care about architecture, security, and the nuts and bolts.
  • Content creators: They don't care how the site works; they just want to publish faster.

By starting with just these two, we can speak their specific language without getting overwhelmed by operational complexity.

Choosing the right channels for your message

Every program is different, but you’ll likely use a mix of digital and personal channels. It’s not about using every tool available; it’s about using the right tool for the specific task.

Email and in-app

Email is still the workhorse of customer marketing because it’s the only way to get a specific message to a specific person at a specific time. 

In-app messaging, on the other hand, is great for quick hits, like signing up for office hours or checking out a new feature. Just don't use in-app messages for deep conceptual learning, and don't distract them from the task they actually logged in to do.

Person-to-person and scaled channels

Don't forget your account teams. They’re a channel too. We’ve had success creating launch kits for CSMs to give to customer champions. This way, the excitement comes from an internal leader rather than a vendor they don't know yet.

If you're dealing with smaller accounts (tech-touch), you can scale the personal feel through webinars, office hours, or digital communities. Retargeting ads are also a surprisingly cost-effective way to stay top-of-mind for customers who haven't logged in for a while.

Operationalizing and measuring success

When it comes to the technical side, don't wait for a perfect data setup. If you ask your dev team for every single data point, they’ll tell you they can get to it in four years. 

Pick the two or three milestones that actually indicate a customer is getting value and focus on those.

Tracking the right metrics

We often dismiss engagement metrics (like email opens) as vanity metrics, but they're useful for understanding which channels your customers actually prefer. However, you eventually need to move toward deep actions.

  • Binary milestones: Did they finish setup? Yes or no?
  • Healthy habits: Are they using the tool in a repeatable pattern?
  • Retention and expansion: While these are the ultimate goals, they can take a long time to show up in the data (especially in multi-year enterprise contracts).

In the meantime, just ask: Can the customer articulate the value they’re getting? If they can’t, you’ve still got work to do.

Coordinating with other teams

If you have instructional designers or support teams, you can’t have two different processes. You have to agree on the goal and the order of operations. Marketing can handle the scaled work – like getting people to take a course – so that the customer success team can focus on the interpersonal relationships that a computer can't build.

Onboarding isn't magic, but when you build a clear, guided path, it certainly feels like it for your customers. Instead of sending a welcome package and hoping for the best, show them exactly how to win.

This article is based on a presentation given by Lauren at our Customer Marketing Summit, Boston 2024.

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