How Cabana Life’s AI Concierge “Jess” Recovered Weekend Sales and Lifted Conversion 5.4x

Cabana Life sells sun-protective clothing to a demographic that skews older — and that demographic has questions. Mostly about sizing and hem length. Before REP AI, those questions had nowhere fast to go.

The Challenge: A Team of One, and a Weekend Problem

Cabana Life’s customer service team was, in Jennifer Kovac’s words, “a team of one.” Their prior tool, Zendesk, only supported email — no live chat — which meant every question became a ticket, and every ticket that arrived on a weekend sat until Monday.

“The majority of our sales and revenue happen over the weekend. So when a customer had a question, there was a good chance we’d miss the sale because we wouldn’t be able to respond until Monday. As a customer, I wouldn’t wait around on a website for an answer - I’d move on. We needed a way to respond instantly.”
— Jennifer Kovac

The friction was concentrated in one place: fit. Specifically, whether a hemline would fall above or below the knee — a make-or-break detail for Cabana Life’s core shopper.

Building Trust Into the AI

Jennifer’s biggest worry going in wasn’t technical — it was whether an older, less AI-native customer base would trust a chatbot. The team’s answer was to make the AI experience feel as human as possible, deliberately: they named it “Jess” (distinct from their human rep, Tracey), matched its interface to Cabana Life’s brand colors so it wouldn’t look like a bolted-on plugin, and let it just do its job.

“I did ask Tracey, our customer care manager, the other day, are people asking if Jess is actually real? And she said no — people are asking her if she is real. The feedback hasn’t been anything about thinking Jess is AI.”
— Jennifer Kovac

Rollout took about three weeks — slightly longer than expected due to an API issue on REP’s side — but Jennifer described the support team as helpful throughout.

The Results

• $4,713.70 in AI-generated sales over the trailing 30 days on $647 in platform cost — a 7.3x return this period, part of $24,371 in AI-generated sales since launch in March 2026.
• 8.71% conversion rate on conversations with Jess — a 5.4x lift over baseline.
• 27 orders rescued this period, 15 shoppers added an item to cart directly in chat without leaving the page, converting at 34% — the standout metric of the engagement.
• 89.68% of conversations resolved by AI with no human needed; 123 support tickets deflected this period (434 all-time).

From Support Tool to Merchandising Input

The add-to-cart feature mattered because it removed a step from the customer journey, but Jennifer says the bigger unlock has been what Jess’s conversations reveal about what customers actually want.

“It’s become a really valuable source of merchandising insights. What prints are customers responding to? What are they asking for? Sizing is a big one, which is why we’re working on making our size chart more clear. Length has also been a recurring theme with our older customers. We had been moving toward shorter lengths, but the conversations we’re seeing are telling us that customers actually want longer styles. So we’re adjusting our product strategy based on what we’re hearing directly from them.”
— Jennifer Kovac

The team also feeds Jess real-time context — current promotions, upcoming new product launches, and the $195 free-shipping threshold — and uses full chat transcripts to hand off warm, informed conversations to Tracey instead of cold tickets. When a wholesale inquiry came through chat, Jennifer used it to update the FAQ and route future leads to the wholesale rep directly.

The Recommendation

“Definitely do it. It’s not just about improving customer service and driving conversions. The customer insights we’re gaining are incredibly valuable — they’re helping us better understand our buyers and, ultimately, what we should be creating and designing for them.”
— Jennifer Kovac, Director of Ecommerce, Cabana Life