AI as the Sidekick, Agents as the Hero: Key Takeaways from Gladly Connect Live 2025
The “gladly-ators” descended upon Nashville Tennessee last week for their annual user conference, Gladly Connect Live. Metric Sherpa sent me onsite to hear the announcements and to speak with CX leaders from a variety of iconic brands in attendance. As conversations unfolded, there was significant excitement about how customer service could be an even more strategic driver inside of the organization.
Gladly CEO Joseph Ansanelli opened his keynote with the question, “How can we achieve radically personalized customer service in the age of AI?” The announcements that followed show that gladly is tripling down on a desire to create unique, distinctive experiences through a seamless agent and AI collaboration.
The Bottom Line
Joseph described two potential paths for the focus of their technology roadmap. The path of “deflection and containment” of service interactions versus the path of enhancing customer engagement. Gladly intends to set itself apart for brands wishing to make moves in the second direction. They announced the following imminent enhancements and features for 2025:
“Sidekick Guide”: This is expected to be released in the next two weeks. This feature intends to make it significantly easier for service workers to train the “Sidekick” AI. Their goal is to make it possible for employees “without a computer science degree” to effectively evolve the AI resource through an extremely simple interface.
“Sidekick Actions”: This feature is Gladly’s splash into Agentic AI. By maintaining a lifelong “conversation” with the customer across all channels, this feature intends to connect Gladly with other key systems across the enterprise. Once trained, the Gladly AI capability will be able to take significant actions on behalf of the customer such as processing returns, changing flights, or making exchanges.
“Sidekick on Voice”: This promises to be a significant step for Gladly’s AI capabilities. This feature makes it possible for a customer to dial a phone number and interface directly with an AI agent over voice. Everything from the actual sound of the voice to the actions it can perform is said to be highly configurable. In theory, this means that a brand can provide immediate support with no hold times at any hour of the day. This feature is also said to integrate seamlessly into SMS, allowing things like order tracking and status updates to happen on mobile.
Ansanelli made a bold prediction that many brands will see phone interaction volume increase due to this type of technology. There is not yet a definitive date for the release of Sidekick on Voice.
Read the Gladly Sidekick on Voice official announcement here: https://www.gladly.com/blog/sidekick-on-voice/
Coming Later in 2025 and Beyond
As Joseph extended his vision a bit further into the future, he demonstrated a prototype of a service worker collaborating with the AI engine in real time. By “bringing sidekick into the hero (agent) experience” Gladly expects organizations will be able to achieve better handoffs, more effectively manage exceptions, and significantly accelerate even complex resolutions.
Additional announcements included a conversational AI reporting engine geared toward leaders called “Sidekick for Insights” as well as a customer-facing conversational AI digital experience called “Sidekick for Sales.”
In Conclusion
While achieving efficiency through enhanced AI capabilities was certainly a theme, the real takeaway from Joseph Ansanelli’s keynote and conversations with CX leaders was Gladly’s commitment to designing “hand-crafted” experiences—ones that blend AI’s power with human empathy. The phrase “Simply powerful” echoed throughout the event, underscoring Gladly’s vision of AI as an enabler, not a replacement.
My personal take?
The “Sidekick to Hero (agent)” concept represents a bold step forward and has tremendous potential. Compared to other AI-enabled agent inferences, the Gladly UI appears clean, fast and powerful. So much of it will come down to how brands choose to implement the technology and how much freedom they award to agents.
Gladly’s vision is clear: AI should empower agents, not replace them. The real question is, how many brands will hyper-focus on the efficiency play and not capitalize on the potential for elevated experiences though AI / human collaboration? Those who do may redefine what the future of customer service looks like.
