How to Make Onboarding a Revenue Multiplier: A Guide for Customer Success

If you’re looking at onboarding as nothing more than a process to set customers up on your software, then you’re missing out on some serious benefits that onboarding can provide the rest of your company.

Onboarding is a critical part of the customer lifecycle. It can set customers up for success (or failure) and provide valuable insights for the rest of your teams. The companies that prioritize onboarding as a growth function are the ones that can retain customers at a higher rate, improve their products faster, and scale to new heights. 

Linnea Olson (Director of Customer Experience at When I Work) and Nina Wilkinson (Partner at ScaleUp CS) joined us for a webinar on this topic to share their views on using customer onboarding as a revenue multiplier. Read on (or watch the webinar) to see how.

Meet the Experts: Linnea And Nina

Nina has managed six Customer Success orgs over the years at companies ranging from Series A to D – including standouts like Apollo, Lob, and Canary Technologies.

Nina has built CS teams in-house while helping individuals build their CS careers, and now, through ScaleUp CS, she partners with B2B companies to build and scale their CS orgs.

Linnea has worked in CS since 2014, managing CS operations at Apollo and Jamf after beginning her career in sales; it was the relationship-based approach to sales that gave her a taste – and love – for the operational side of Customer Success. Currently, Linnea heads Customer Experience at When I Work.

Together, they have over a decade of CS leadership experience, making them the ideal experts to guide you on this topic as you consider scaling your CS team.

Onboarding Is a Must-Have, Not a Nice-to-Have

If you don't teach your customers how to use your services, your platform, or your functionality, why even bother selling to them in the first place? 

It’s rare that a CS team doesn’t care about onboarding, but it’s common that a CS team will be drowning in their company’s chaos and unable to use onboarding strategically.

Startups are always chaotic, though. But onboarding usually suffers from one or more of the following:

• Inconsistent onboarding experiences
• No clear definition of success for customers
• No way to measure onboarding ROI
• No dedicated onboarding person

Or all of the above. If you’re experiencing these, then don’t worry – it’s normal. But you don’t have to take it at face value either. Nina and Linnea shared a unique approach to onboarding that transforms it from a chaotic process to a growth driver for the rest of the company.

The Hidden Revenue Opportunity Behind Onboarding

Does this sound familiar? 

You’re in a Slack channel with your sales team, and a rep posted that a new deal closed, to much fanfare in the way of emoji cakes, bells, and fireworks. Then your founder hops in and says he knows the customer, has a relationship with their CEO, and wants to handle onboarding personally. 

This “all hands on deck” mentality is part of what makes startups fun, but it also leads to customers being lost in the chaos. 

Without a streamlined, operationalized approach to onboarding, the experience will vary based on whoever is available at the moment, and that is a recipe for a poor onboarding experience that allows customers to silently drop off in their first month.

63% of customers say that onboarding is key to whether they subscribe in the first place and stick around, and 86% claim they will stay longer if you offer a solid onboarding process with continuous education. You don’t need to be a math expert to see that onboarding is your fastest path to improving GRR or NRR. 

An Example From Apollo: How Onboarding Drives Retention

Linnea and Nina shared their firsthand experience leading CS at Apollo. Apollo is a sales data platform with four primary product lines and additional add-ons and upsells. 

While at Apollo, they focused the onboarding team on getting customers to try at least two base products and one add-on. Then, the CSM team (measured against product adoption) focused on getting accounts to engage with the product, providing the team with a leading indicator for upcoming renewals.

The CS team also collaborated with Apollo’s BI team to run an analysis of their customers to predict renewals and churn based on product adoption and answer questions like:

• If a customer used three products, what was their likelihood of renewing? 
• How many of those customers actually got to renew or potentially expand on the platform? 
• If they used all four products, what did that number jump up to? What did our retention metrics look like? 
• What could they predict in terms of that renewed health? 

This information was critical and enabled the CS team to have strategic conversations about increasing adoption to drive renewals, rather than looking back and wondering why customers churned.

It also put CS in a position to drive renewals and upsells more reliably, both key parts of Apollo’s growth strategy. You may not earn all the Slack emojis that your sales friends do, but there is no denying that onboarding is one of the best levers for sustained revenue for your business.

Reframe Your Onboarding: From Chaos to Compound Interest

Turning onboarding into a revenue multiplier begins with reframing your approach. 

Userpilot conducted a study in 2024 that found 74% of customers will churn due to a poor onboarding experience. More often than not, churn doesn’t happen at “month 11,” it happens in the first 45 days. That’s because the first 45-90 days with your product are a critical period where customers will judge how well you can help them achieve their goals.

If integrations stall or APIs fail, your NRR is dead on arrival, and your CSMs have a steep uphill battle ahead. This is where onboarding isn’t just a problem for Customer Success, but becomes a problem for Product and the rest of your company.

Beyond improved retention and revenue metrics, onboarding has another sneaky benefit most chaotic CS teams miss: it gathers intelligence for every other department in your company.

Here are a few examples:

• Executive team: Every milestone you hit is a leading indicator for GRR, and NRR is storytelling ammunition to use at board meetings. 
• Marketing: Partner with marketing to identify the best customers, define your ideal buyer personas, and highlight successful customers with case studies.
• Sales: Share customer success stories with sales to narrow down your ideal customer profile and partner with sales on clean handoffs from closed deals to onboarded accounts.
• Product: Share gaps and stumbling blocks with customers in your product and engineering teams. This can help your product team refine the product, improving the customer experience and your onboarding process.

And all of this combined fuels the PLG (Product Led Growth) motions in your company. The faster you learn from your customers – what works, what doesn’t, how to get them to value faster – the more those learnings can carry over to the rest of your company.

How to Balance Your Company’s View With Customer Value

We’ve established that onboarding can drive revenue and retention for your company, but you can’t ignore your customers’ perspectives in all the excitement. 

Far too often, we focus on onboarding purely from our perspective: what we want, our goals, our metrics, etc. But successful onboarding starts with a stellar customer experience, and that means bearing in mind what your customer cares about as they work through your onboarding steps:

• Can I actually use this? 
• Did I buy the right thing? 
• Did I make the right choice? 
• Will your team be able to support me in the long run? 

Yes, you should balance the above with your team and company goals, but you need to bear in mind where your customer is coming from. When those two sides align, that’s when you know your onboarding process is done correctly.

How to Drive Value From Onboarding: Go Beyond Feature Adoption

The key to everything we’ve covered so far is that you need to drive real, quantifiable value for your customers within the first month. 

That means doing more than simply sending a checklist to complete. Checklists are great; we all love them. But checklists are good for giving customers a workflow to follow, and not driving the kind of value that will keep them in the long run. 

The answer is to attach a benefit to every onboarding step.

Every setting toggled, item created, and integration connected needs a benefit attached to it. Customers won’t always remember your product's features, but they will remember the benefit they got from using it.

Focusing on benefits over features can help you shorten that magical metric: time to value. Customers who hit that time-to-value within their first 14 days renew at a 2x higher rate. For more complex products, which might be longer, the point is to drive it as soon as reasonably possible, given the complexity of your product.

Seeing Revenue Gaps? Solve Them With The Great Revenue Mystery

Onboarding is more than a mere formality or series of hoops to jump through; it’s one of the strongest predictors of renewal in your toolbelt.

To get onboarding right, though, you’ll need time and tooling to invest in your onboarding process. CS teams know this. What’s harder is demonstrating their value and impact to the rest of the org. We surveyed 400+ CS and business leaders to better understand how they measured the business impact of their work.

We wanted to know:

• What metrics did they track
• How did they quantify success
• The value CS provided

And more. You can read the results of the survey and learn how to demonstrate the value CS has in your org by clicking the button below.