While onboarding is often viewed as the start (and sometimes even the finish line) for customer education, it is just one milestone in a much broader customer learning strategy. To the experienced customer education leader, onboarding is a moment in a journey that begins before purchase and continues long beyond.
In our recent webinar, Tom Studdert, VP of Customer Experience at Ensora Health, joined us to unpack how, when built and measured the right way, customer learning can be a growth engine that improves adoption, boosts retention, and even influences the pipeline. Watch the webinar on demand here, or keep reading for some insights from the event.
Reframing Education in Business Terms
Tom opened with a phrase he coined early in his tech career: “training equals retaining”. It’s simple, but it lands because it forces a mindset shift. Customer education isn’t just about teaching people where to click, it’s a vehicle for the outcomes the business actually cares about: retention, renewals, expansion, and revenue.
That’s why Tom challenges the way onboarding is commonly measured. Many teams track time-to-value or time-to-first-value, and while those metrics are useful, they’re not the end goal. In Tom’s view, onboarding should ultimately be measured by product adoption, by understanding when customers are using the product to the fullest extent that allows them to be successful.
This is not product adoption as the business defines it, but adoption as customers define it. Success isn’t “they completed the onboarding checklist.” It’s “they’re using the product in a way that creates value for them.” When you get that right, the chain reaction becomes clear. When customers use your product in a way that creates value for them, they are going to renew, and that leads to more revenue, more lifetime value, more cross-sell and upsell opportunities, and so on.
And in Tom’s own words, as “no one can adopt a product they don’t know how to use,” education is the bridge between onboarding activity and long-term customer outcomes. And onboarding is just the first step in getting to those outcomes.
Connecting the Dots: From Onboarding KPIs to Retention
It can be tough to draw a direct line from onboarding metrics to retention, so Tom’s advice was to think about product adoption as the “middle dot.” Going straight from onboarding to retention can feel like a stretch, but when you map onboarding KPIs to adoption behaviors first, the story becomes much more defensible.
Tom shared an “adoption ladder” that covers five steps which move customers from early, tactical usage to full ROI adoption. The early rungs look like what most onboarding teams focus on today, such as core features, basic functionality, and initial workflows. The goal is to guide customers up to a point where they’re using the product with minimal guidance, where it’s deeply embedded into how they work.
From there, work with a data analyst to understand how that product adoption correlates to retention and growth. You should already be able to see that those customers who have gone through onboarding and participated in education programs are using the product more, giving you that initial business case for what you’re providing with education. The next step is to be able to show that trained users are more likely to buy more, and more likely to renew.
Tom’s key point here is encouraging: you don’t need a perfect BI team on day one. In one of his early roles, he started with an FP&A partner who was simply a wizard in Excel! Over time, that matured into more robust analytics support. What mattered was starting with the right line of inquiry.
Speaking the C-Suite’s Language (and Getting Buy-In)
When the conversation shifted to executive buy-in, Tom was candid. Early in his tech career, he didn’t naturally think in “C-suite language.” So he did something most teams don’t do, he interviewed his executives, asking them a direct question: What do you need from me so you can do your job successfully?
He then started building out an understanding of what each executive role was looking to achieve:
- CCO / Customer leadership: retention, renewals, customer health
- CRO / Revenue leadership: upsell, cross-sell, expansion revenue
- CPO / Product: adoption and usage of key features
- CMO / Marketing: leads, advocacy, audience growth
- CFO / Finance: cost to serve, efficiency, profitability
- CEO: all of the above, as well as alignment across the business
Once Tom aligned education reporting to those outcomes, the response changed. Because when education is framed as a driver of value, not a set of training activities, it stops being seen as “cost of service.”
Tom credits this shift as a major reason he was able to grow an education team dramatically over time, because he wasn’t asking for headcount for headcount’s sake. He was showing how education affected retention and revenue. He even shared a moment where a CEO literally applauded in an operating review because, in his words, Tom had “finally got what I care about.”
There’s also a language component to making sure the C-suite cares about what you’re doing. Tom shared how when he started out, he paid close attention to the all-hands meetings and emails the CEO was sending out, and learned to stop talking about activities, and start talking about outcomes.
Instead of how many courses you offer, talk about how those courses lead to the outcomes the business wants, framing education as a revenue multiplier instead of a cost center.
“Don’t talk about how much you’re spending. Talk about how much you’re bringing in the door. Speak to strategic leverage and position education as a driver of customer success.”
Measuring ROI Without Getting Overwhelmed
For leaders just starting out, Tom suggested a five-step approach:
- Define program goals and align them to business outcomes (not just “how many trained” but how those trained users impacted retention or renewals.)
- Create engaging content across modalities.
- Target the right audiences and decide where training should be segmented, keeping costs in mind such as where training should be self-service vs. personalized.
- Personalize learning to how customers actually work and to what suits each audience.
Leverage technology and reporting where leadership already lives (CRM + BI tools, not just LMS dashboards)
Education as a Lead Generator
One interesting point in the discussion was a focus on Education Qualified Leads (EQLs). Education can influence the sales or revenue pipeline,, even if teams don’t always acknowledge it. Too many times, Marketing handles leads, and Customer Education does training, and never the twain shall meet. And yet, we’re all in the business of revenue and retention.
Tom argued that mature education programs can move early, building credibility, creating market awareness, and reinforcing brand leadership, instead of adding education late in the sales cycle, when prospects are near the finish line.
He shared three ways education can support pipeline:
- Make parts of your learning hub accessible beyond paying customers
- Open your knowledge center to your total addressable market
- Offer select public courses (free or paid) to showcase expertise and value
These tips help you to sell your value really early on with the thought leadership you demonstrate, sneaking in the product as part of making people’s role easier in their day to day work.
Ready to take it deeper?
This webinar was bursting at the seams with actionable content to help boost customer education programs up the maturity ladder. Watch the full event to learn:
- More about the data you need, outside of what’s sitting in your LMS.
- How to use customer communities to augment customer education.
- Positioning education as a strategic lever alongside customer success.

