How Sun & Ski’s AI agent “Sunny” turns approachability into sales.
A fast-growing outdoor retailer transforms seasonal bumpiness into year-round sales by deploying an AI agent that matches the expertise of their best in-store associates
Conversion rate increase
3x
When Sicily Dickenson joined Sun & Ski Sports as CMO and Head of E-commerce in 2022, the Texas-based outdoor retailer was at an inflection point. They'd built a thriving brick-and-mortar business opening stores in unexpected markets and then expanded to resort markets. But customer behaviors were shifting, and the brand wanted to do more than just keep pace. Three years later, Sunny, their AI agent, has improved CSAT by 50% and tripled product page conversion rates…and they’re just getting started.
At first, the company set its sights on evolving from a predominantly in-store experience to a robust omnichannel operation. They faced a specific challenge: how do you scale the deep knowledge of your best outdoor experts who can guide both first time and black diamond skiers and snowboarders through complex decisions about skis, boards, boots, and bindings—across digital channels?
Meanwhile, Sun & Ski's business is intensely seasonal, with most revenue happening in a 3-4 month winter window. This creates massive customer service spikes that historically required hiring a new crop of temporary representatives each year—a costly, disruptive cycle of recruiting, training, and managing seasonal staff.
Starting small, thinking big
Marcus Tyree, Sun & Ski's CFO and Head of Software, saw an opportunity. With a background spanning corporate banking and technology transformation work with Fortune 500 companies, he believed AI could help Sun & Ski achieve the expert knowledge depth of their best associates, with the asymmetric upside of digital delivery.
"I thought there was a unique opportunity for us to have a very approachable and knowledgeable conversational AI agent where people could ask it anything, at any time of day, and actually build that trust and confidence," Marcus recalls.
But selling that vision wasn't easy. The co-owners needed convincing. And Sicily? She was drowning in priorities, racing to build e-commerce infrastructure before the peak winter season.
Marcus chose to partner with Sierra, betting on technology that was ready to deliver results immediately. He decided to start with simple use cases that would scale with seasonal demand, like handling basic returns and order status inquiries.
As Sicily's team watched the agent, affectionately named “Sunny,” answer increasingly sophisticated product questions, they had a realization: this could be so much more than support.
Sicily had been exploring an expensive third-party tool to answer product questions on detail pages, but decided to pause the process. After all, a better option was already in motion. Sunny moved beyond support into sales.
An approachable expert who never intimidates
Sunny's personality reflects the Sun & Ski Sports brand. She’s friendly, warm, and approachable—a direct contrast to competitors who often have intimidating, hardcore vibes that scare off novice athletes.
"You can ask Sunny anything. Sunny will never intimidate you," Sicily says. "There are a lot of questions people ask Sunny that they would never have clicked on a chat, picked up the phone, or sent an email about."
“You can ask Sunny anything. Sunny will never intimidate you. There are a lot of questions people ask Sunny that they would never have clicked on a chat, picked up the phone, or sent an email about.”
Sunny helps shoppers by asking expert-level questions: What's your skill level? Powder or moguls? Which resorts? She handles the complexity of outdoor gear—will these skis work with those bindings and boots?—with remarkable depth.
"It's surprising how she can personalize in ways that aren't scalable with one human on a phone," Sicily reflects. "Sometimes I'd see a conversation about skis where Sunny asked if they were a beginner or advanced skier—okay, normal question. Then she'd ask about powder or moguls. Then where they're skiing, what resorts. I'm like, I'm not sure if one of our outdoor experts could have even had this level of conversation unless they were from that particular area."
Numbers tell the story: From connection to conversion
The results have been remarkable. Sunny achieves 90% customer satisfaction compared to 68% for conversations transferred to human agents. Customers who engage with Sunny convert at triple the rate of those who don't.
She's handled thousands of after-hours conversations in just three months. "Those are conversations we wouldn't have fielded until the next day, if at all," Sicily notes. "That is really helpful for us—and is helping us raise our customer satisfaction overall."
And perhaps most impressively: despite growing e-commerce substantially year-over-year, Sun & Ski hasn't hired a single seasonal customer service agent this winter, eliminating the complexity of recruiting, training, and managing temporary staff during their crunch period.
The shift in Marcus's thinking was profound: "There's a lot of people who see AI as immediately an expense-saving tool, but the true leverage is conversion. It starts with connection, which turns into conversion."
“There's a lot of people who see AI as immediately an expense-saving tool, but the true leverage is conversion. It starts with connection, which turns into conversion.”
And Sicily has experienced a shift as well: "Honestly, in the beginning, I did it for Marcus. I just wasn’t sure this was one of our highest priorities, but now? This is probably one of the most impactful things we'll do this fiscal year."
