Chris:
Nick, in the words of Taylor Swift, you’ve had your fair share of “eras”—from customer success pioneer to architect of the customer OS, and now this new phase with Skilljar. What era are we entering now for customer education?
Nick:
(Laughs) That’s a great way to frame it. I’d say we’re far past customer education’s debut era—definitely out of “Fearless” and “Speak Now.” Today, customer education is integrated into a much broader ecosystem—CSM, onboarding, training, community—it’s all blending into one cohesive journey. That’s why at Gainsight we talk about the “Customer Operating System.”
Sandi:
Well, if we’re sticking with Taylor Swift, I’d say we’re in the “Midnights” era. When Skilljar started, we were still in the “Fearless” phase—trying to define what customer education even meant. Then we moved into the growth and chaos of SaaS, maybe the “Reputation” and “Folklore” phases. Now, we’re in a more reflective space—really getting to the heart of what customer education is all about.
Chris:
Sandi, Skilljar is known for the mantra “trained customers are your best customers.” Was there a moment when this shifted from a belief to a proven business truth?
Sandi:
I’ve always believed it. I don’t come from a SaaS or L&D background—I came from Amazon, where customer-centricity was just a given. So the idea that training your customers is valuable felt obvious. I’ve never understood the whole correlation vs. causation debate around customer education. Do we really think untrained customers perform better?
That said, the first real data came from Asana around 2018 when Daniel Quick was there. They did an A/B test showing how training impacted free-to-paid conversions. Since then, dozens—if not hundreds—of companies have shown that training improves product usage, retention, expansion, NPS, and reduces support tickets.
Chris:
Nick, when did customer education click for you as something more than just a support or CSM function?
Nick:
Early on at Gainsight, our CSMs were doing 1:1 trainings—literally on WebEx. It was effective but not scalable. We needed a better solution, so we started using Skilljar. We built an academy and launched a certification program. The impact was huge.
For example, our NPS for non-certified customers was 36. For certified customers, it was 72. That’s a massive jump.
Then I spoke at Skilljar’s Connect conference and saw firsthand the passion of this community. That was another inflection point for me.
Chris:
Sandi, you’ve described the risk of treating customers like “frozen blobs” at the moment of sale. Can you elaborate?
Sandi:
Absolutely. We’ve had Skilljar customers for nearly 10 years—and in that time, we’ve seen them go public, get acquired, go through multiple reorgs, and change product strategy. Their users and business goals are constantly evolving.
If you treat your customers like they’re static, you quickly fall out of alignment. Customer education gives you a way to continuously meet the needs of a changing learner base—different roles, different goals, different levels of expertise.
Education becomes this always-on, scalable support system—what I call “passive onboarding” or “passive income” for your customer experience.
Chris:
A lot of SaaS leaders say things like, “We don’t need an academy yet,” or “Our product is intuitive.” What’s your message to them?
Sandi:
Honestly? That’s hubris. If your competitors aren’t doing it yet, that’s your opportunity to get ahead.
And let’s be real: if you’re a growing SaaS business, you’re already doing education. Your CSMs and support reps are spending a huge chunk of their time training users informally. That’s shadow training. Why not formalize it and make it scalable?
Nick:
Totally agree. Products are less differentiated now, and customer loyalty is fragile. You have to re-earn their business constantly. Throwing more people at the problem isn’t sustainable.
CSMs jumping in after something breaks or after usage drops isn’t proactive—it’s reactive. Education is your proactive, durable strategy for scale.
Nick:
What really excites me is thinking beyond retention. Customer education is about helping people grow in their careers—getting promoted, switching roles, achieving their goals. That’s the deeper impact.
I’ve had customers tell me our academy helped them get a raise or feel more confident in their job. That creates real advocacy—and it’s incredibly sticky.
Chris:
That reminds me of HubSpot. We used to get messages from people saying their certification helped them get hired or even take their family on a vacation. That’s the ripple effect.
Chris:
Let’s talk about AI. As we move toward prompt-based interfaces and agentic workflows, what does that mean for customer education?
Sandi:
Great question. As UX becomes more invisible—just a search bar or prompt—the user has less context. That means more education is needed, not less. People will need help understanding what to ask, how to phrase prompts, and how to use these tools strategically.
There will also be a growing need for training new roles—like the people feeding data into AI models. That’s a whole new function.
Nick:
Agreed. AI is reshaping jobs, not just software. If your product helps marketers, for example, you now need to teach them how to do an entirely new kind of marketing. Education has to expand to cover those new paradigms of work—not just features.
Chris:
Are we seeing customer education evolve into a full go-to-market strategy?
Nick:
Yes. With AI, the sales process is the customer experience. You turn on the product, start using it, and decide based on that. Gainsight is doing it. Many others are too.
Selling work—not just software—requires education to be part of the entire buyer journey, from top of funnel through renewal and expansion.
Sandi:
If I could give one piece of advice: go through your onboarding flow like a first-time user. It’s humbling—and builds empathy.
Nick:
And if you’re saying, “We’re not ready for this,” what you’re really saying is, “We’re not ready to retain customers or make them successful.” That mindset needs to shift.
This is about helping people succeed—not just with your product, but in their work and their lives.