How Notion Scaled Customer Success and Digital onboarding scores by 14pp

Notion built its name the way few companies do — from the bottom up. Community and product-led growth made Notion a tool millions of people use to run their small business, their personal life, and now, the enterprise. But moving upmarket and selling to businesses changed their business model and the product itself. As Notion went AI-native — from a wiki to AI chat and meeting notes to custom agents and to a powerful AI operating system — the job of customer success grew right along with it.

Bo Sun, as the global head of customer success, first saw the opportunity within his own team. CSMs were capable of doing three things at once: consultative, technical, and now commercial. As CSMs got deeper with their dedicated accounts, there was a risk that the customers without a dedicated CSM could be left behind.

That long tail was the segment Kevin Cai, Head of Digital Customer Success, focused on since he joined Notion’s CS team four and a half years ago, when the digital motion was still in its infancy. The one number everyone watched – monthly active members – said something about usage, but little about whether a customer was actually getting value. Scale and care, in other words, were being treated as a trade-off.  Notion needed more than a collection of point tools – they needed a single operating system for customer retention. With Gainsight’s Customer Retention Platform, Bo’s team could finally connect digital programs, health scoring, and renewal workflows in one place, giving them the visibility to act before risk became churn.

Shortly after joining Notion, Bo created a global digital leadership role for Kevin. He replaced monthly active members with net revenue retention (NRR) as the number every CSM was measured on, and merged the renewals motion into CS, so the team finally carried revenue rather than just usage.

Then he reframed what digital was capable of. Not a lesser substitute for a human CSM, but something a human never could be: “imagine a teacher who isn’t lecturing to the entire classroom at once, but rather sitting on each student’s shoulder, providing the most relevant and achievable next step”. “I see scale and care not as an either/or but as an and to our dedicated CSMs,” he says. That distinction – and, not or – became the brief for everything Kevin built next.

That brief reached past software and into Notion’s own teaching material. Notion Academy — the library of polished learning content and certifications that a partner team runs on Skilljar — gave the digital motion something to deliver, and digital gave the Academy a way to reach the right customer at the right moment. “The education team and Notion Academy are critical to the success of digital,” Kevin says. His team shapes that content to fit what enterprise customers need, then uses digital as the channel to get it into their hands. Next on the list is wiring Skilljar into Gainsight directly, so CSMs can see which accounts have certified admins and how many users have cleared the basics.

Gainsight’s Journey Orchestrator — the automation engine for building and triggering multi-step email and in-app programs — became the backbone of the new motion. Kevin built onboarding journeys along with post-onboarding and pre-renewal surveys, and then the program he’s proudest of: three “archetypes of risk” — failed-to-launch, steep decline, and slow decline — that he mined from the data himself and codified with his Gainsight TAM into per-account signals. For digital accounts, a flagged archetype fires a journey automatically, with no human in the loop; for CSM-managed accounts, it pings the CSM instead so they can use their judgment on what to do next. The same signals feed a weekly digest for managers and leaders.

Piece by piece, Kevin built a powerful digital system. Along the way, Gainsight became, in Bo’s words, “a source of truth for our customers”.

The payoff showed up in the numbers Kevin used to make his case internally. Onboarding scores in digital increased by 14pp, Kevin says, with a 13pp lift in green health accounts. 

Those results didn’t just validate the program, it’s what justified expanding the role in APAC and EMEA, and eventually a promotion to lead all of it globally. “Gainsight was instrumental for me to be able to prove value and scale,” he says.

And he doesn’t think the story is finished. With Gainsight’s MCP and AI now in front of him, Kevin sees the next chapter as bigger than the foundation he spent years laying. “What is possible now with digital CS, we only were dreaming of two years ago,” he says. “It literally was not possible. I’m excited to see where the future takes us.”