In a digital world shaped by convenience and connection, the customer journey has evolved into a two-way conversation. In this CommerceNext webinar, leaders from Boot Barn, Billabong/Quiksilver, Sideshow and iAdvize explored how conversational commerce is transforming product discovery, driving conversions and helping brands build long-term customer relationships through smarter engagement.
Moderated by Allan Dick, Co-Founder of CommerceNext, the discussion covered everything from the power of real-time AI to the evolution of chat tools, customer expectations and building customer connection at scale.
What We Learned:
- Rethink the role of chat—don’t limit AI to a chatbot.
- Use conversational tools to simplify complex product decisions.
- Layer AI with human support to build authenticity and trust.
- Personalize engagement based on shopper behavior and demographics.
- Train your internal teams to shape and own AI experiences.
Speakers:
- Justin Hanley, Director of Data Science, Boot Barn
- Natasha Trout, Director of Merchandising, eCommerce, Oved Group (Billabong/Quiksilver)
- Chris Pirrotta, VP of Marketing, Sideshow
- Mike de la Cruz, President, iAdvize
- Moderated by: Allan Dick, CoFounder, CommerceNext
Watch the replay here or read the recap below.
Beyond the Chatbot: Creating Conversations That Convert
De la Cruz, iAdvize, kicked things off with a bold idea: “Fire the chatbot.” He urged brands to rethink the limits of traditional chat experiences, which often only engage 1% of site visitors. Instead of confining AI to passive chatboxes, leading retailers are using intelligent assistants to proactively guide customers through the funnel, without interrupting the shopping experience.
Whether helping shoppers find the right gift, offering product education at the PDP level or acting as a virtual stylist, these AI-powered touchpoints deliver value where it matters most. These initiatives have seen a 13% lift in conversion and five times more engagement when implementing interactive, helpful assistants that act more like in-store associates than clunky pop-ups.
CX That Learns and Adapts in Real Time
At Boot Barn, Hanley explained how the brand is using a custom language model and generative AI to power “Cassidy,” their in-store and online shopping assistant. Customers often have technical questions—especially about sizing or work boot specs—and Cassidy provides real-time answers, personalized recommendations and product locations to help users feel confident in their purchases. This tool also helps shy or hesitant customers navigate complex buying decisions with less friction.
Trout, Oved Group (Billabong/Quiksilver), shared a similar challenge. Technical products like wetsuits require detailed education. To combat this, conversational tools give first-time buyers the confidence to convert quickly. The result? Brands see reduced cart abandonment and increased trust across unfamiliar categories. Trout also emphasized the importance of tailoring engagement by demographic, noting that some audiences engage more with chat, while others prefer traditional filtering and guides.
From Fan Chats to Frictionless Journeys
For Pirrotta, the connection between customer and brand is deeply emotional at Sideshow. With a high AOV (Average Order Value) and a passionate fandom, the brand has fully embraced AI—without compromising authenticity. Their conversational assistant references specific characters and franchises to ensure relevance, while Sideshow’s ambassador program lets superfans engage with fellow collectors in real time.
This layered approach has been game-changing for Sideshow, helping deflect 90% of support inquiries while keeping conversations natural and aligned with brand voice. Fans are rewarded with loyalty credits for acting as brand ambassadors, creating a scalable human experience that still feels personal. “We couldn’t staff 24/7 support without this,” Pirrotta said, “but now we can do it in a way that’s better than we ever could with just full-time staff.”
Authenticity and AI Can Coexist
As brands embed AI deeper into CX, authenticity remains non-negotiable. The panel agreed that customers should know when they’re interacting with a bot—but that doesn’t mean it has to feel robotic. At Sideshow, early AI tools referenced pop culture and even used animated gifs to set the tone. At Boot Barn, copywriters helped shape the tone of generative content to match the brand’s voice and style. In both cases, AI wasn’t replacing humans—it was amplifying them.
Real-time engagement isn’t just about responding faster—it’s about being more thoughtful, helpful and aligned with what the customer actually needs. Brands that embrace conversation-driven commerce aren’t just boosting conversions—they’re building community.
For more insights like these, register for the 2025 CommerceNext Growth Show, June 24–26 in NYC. Register here.
