60% of Calendly’s Community Content Is Now User-Generated—How They Made It Happen With Gainsight

Calendly, a leader in scheduling automation, had a support-focused community that wasn’t getting engagement beyond troubleshooting. To encourage new ideas and use cases, they needed to make their community a space where users could share creative, real-world workflows in an accessible, inspiring environment. Using their existing instance of Gainsight Customer Communities (CC), they reimagined their community strategy. Now, 60% of their community content is user-generated, with customers learning from one another and pushing the product in new directions.

Calendly had built a successful customer community that was focused primarily on customer support, effectively problem-solving user issues at scale. They did a great job at deflecting tickets via peer-to-peer troubleshooting, while creating a living knowledge base that grew over time.

But as Calendly’s business grew, their customer base became more diverse, spanning everything from individuals and small, informal groups to enterprises with thousands of employees. To take advantage of the growing versatility of their product, they wanted their community to become a place where customers could share and explore unique use cases.

The challenge? Their traditional support strategy was too reactive, redundant, and narrow in scope to deliver on that objective.

Their support-focused community was also overly transactional—many customers only visited when they wanted to fix a problem, in the moment. That meant Calendly was missing opportunities to engage with customers in other ways, like surfacing new product applications or workflows.

“They’re not coming to you in a place of discovery,” explained Jillian Bejtlich, Senior Manager of Community at Calendly.  “We wanted to have conversations that sparked creativity, and also make it so that contributions were actually pushing our internal teams to innovate and create and do things they’ve never done before.”

The team saw a chance to move beyond support and build a space where customers could embrace their creativity, swapping ideas and sparking inspiration. To get there, Calendly needed to figure out how to leverage their instance of Gainsight CC even better.

Calendly used Gainsight to help them deploy a “solution engineering” approach to their customer community. Solution engineering means creating a space for customers to have goal-driven conversations around the product, encouraging interactions that come from a place of curiosity and exploration.

With Gainsight, they made adjustments to their existing community to allow for more unstructured interactions, without having to create a separate solution engineering space. For example, they eliminated the requirement for customers to complete a complicated form when submitting a post. Design choices like these made the community more accessible to new users.

Their goal was to keep the platform open and easy to navigate, encouraging users to post questions, share wins, and learn from each other. These real conversations became the community’s backbone.

“If customers want to talk about kittens or funerals or fly fishing,” Bejtlich said, “we let them do that, focusing on their goals. We meet customers where they are.”

As users share unexpected applications of the Calendly platform, their stories demonstrated Calendly’s flexibility and inspired other users to try new things.

With Gainsight, Calendly’s community has become a user-led product exploration engine, with 60% of posts now generated by the customers themselves. The result is a self-sustaining cycle: users find help and inspiration, which in turn helps other customers, which leads to even greater engagement.

Solution engineering has also benefitted Calendly’s Product team. User conversations around product usage gives them a front-row seat to what matters to customers, and also provides real-time feedback that impacts the product roadmap.

Peer-led support has reduced the volume of repetitive queries within the community, improving efficiency for both customers and the Support team, who can devote more energy to engaging in higher-value conversations.

“Our new approach helps us tap into niche industries, workflows, and segments that we had never imagined,” says Bejtlich. “Not only does that inspire and aid other customers, it also surfaces new customer personas that we were unaware of.”

Calendly plans to continue investing in its power users, the champions who stretch the product in unexpected ways. The plan? Highlight more of those stories, build tighter feedback loops, and make it easier for new users to find ideas that work.

Internally, the company is pursuing structural changes to integrate community-derived insights even more deeply into product development and onboarding strategies. By tying these insights into the customer journey, Calendly aims to help users discover new features in context, intentionally, not by accident.

The takeaway: Calendly isn’t just building tools. With Gainsight, they’re building a community that helps people do more with what they already have.