Why Gainsight’s Acquisition of Skilljar Is a Big Deal for CX

Yesterday, Gainsight announced their acquisition of Skilljar—and this is big news for anyone working in customer education, community, customer success, or the broader customer experience space.

I’ve been operating in and around this space for over seven years now. I’m Sam—founder of AlignedCX, an end-to-end customer experience optimization agency. Before that, I was the Senior Director of Go-to-Market Strategy at Docebo, and I led customer education at Shopify.

Not only have I been a buyer of this kind of technology, I’ve studied the market deeply. And from where I sit, this acquisition matters. A lot.

A Step Closer to the Seamless Customer Experience We’ve All Been Talking About

Even just on the surface level—what the customer actually sees—this acquisition gets us one step closer to the kind of cohesive experience we’ve been dreaming about (and customers have come to expect).

For years, we’ve been talking about the need to unify:

• The customer academy

• The community

• The knowledge base

• The in-product experience

And now we’re finally seeing momentum.

When education, community, knowledge, and support strategies are better integrated, we unlock some pretty compelling use cases:

• CSMs can assign personalized learning journeys

• We gain visibility into how customers are engaging across properties

• CSMs get the data they need to be more strategic and deliver more value

But even that isn’t the full story.

The Real Unlock Is the Data Infrastructure

This is the part most people don’t see—but it’s the piece that makes hyper-personalized customer experiences possible at scale.

When I was at Shopify, I led global customer education across 2M+ merchants. (That little thing on my shelf? It’s from the day we hit that milestone.)

And even back then—before the AI boom—I had a vision for what was possible: Hyper-personalized customer experiences, driven by behavioral data.

We were already tracking so much:

• Platform usage

• Feature adoption

• Where users got stuck

• Content engagement

• Conversion pathways

• Emails opened

• Courses taken

• Community activity

• Support tickets

• CSAT, NPS, login frequency...

The amount of data was insane. But it was fragmented. Siloed across systems and teams.

And even though I knew machine learning or AI could make personalization at scale possible, I couldn’t get it to happen. Not without the right infrastructure.

Fast forward to today, and most companies still haven’t figured this out.

That’s Why This Acquisition Matters

The core issue remains: the systems are still disconnected.

You’ve got your academy over here.
Your community over there.
Your product data in some other stack.

No unified view. No backend infrastructure connecting the dots.

That’s what makes this acquisition such a power move.

Skilljar is one of the best customer education platforms on the market.
Gainsight, meanwhile, has been quietly evolving into a full-blown customer experience optimization engine.

They’re already pulling in:

• Product telemetry

• CS automation

• Community data

• Digital CS motion

Now add Skilljar to the mix and you get incredibly close to a system where product usage, learner behavior, content engagement, and success interactions live together in one place.

But Let’s Be Real...

This kind of integration won’t happen overnight.

Someone commented on Adam Avramescu’s LinkedIn post saying, “Just because Gainsight made this acquisition doesn’t mean the data will suddenly be visible across the stack.” That’s totally right.

The silos still exist.

The real unlock will come when Gainsight connects the data on the backend—when it becomes interoperable and actionable. And yes, that will take time.

But the intention is there.
The foundation is being built.

And once the data becomes visible and actionable? That’s when we officially move from reactive enablement to personalized, intelligent customer experiences at scale.

The Buyer Is Evolving—and the Tech Needs to Evolve With Them

It used to be:

• Customer Education bought the LMS

• Community teams bought their own tool

• CS had its own platform

• Product owned product analytics

Everything—and everyone—was siloed.

But that’s changing.

We’re seeing the rise of the Chief Customer Officer—a cross-functional leader asking bigger questions like:

• How does our product deliver value against jobs to be done?

• What experiences are we layering on top to reinforce and expand that value?

• How do we connect education, marketing, CS, and product across the customer journey?

• How do we align around shared outcomes and OKRs?

This Is Bigger Than Customer Education Maturing

If we’re serious about delivering proactive, value-led, digital-first experiences across the post-sale journey, then this acquisition puts Gainsight and Skilljar in a completely different category.

This isn’t about stitching together point solutions.
It’s about building an integrated foundation for orchestrated, connected, and data-informed experiences.

This is Customer Experience becoming a strategic function—
A lever for growth.

We’re seeing:

• Team structures evolve under the Chief Customer Officer

• New frameworks like service design gaining traction

• And now? The tech finally catching up

We’re on the brink of something big. And this acquisition is a signal of where the industry is heading next.