How Windstar Cruises increased conversion 2% and contained 70% of chats with Cresta

About Windstar Cruises

Windstar Cruises is a small-ship cruise line known for taking guests to places larger ships can't reach, with a level of service that has built fierce loyalty among repeat travelers. The brand's reputation is built on the crew, on the ships, and on a guest-centric philosophy that runs through every decision the company makes.

"At Windstar Cruises, we are really guest-centric," said Chris Prelog, President. "Everything turns around the guest."

That philosophy doesn't start when a guest steps onto the ship. It starts the first time they reach out.

"We want to make sure it's not just the destination, but it's also the journey that they're enjoying," said Jaymi Fiveash, Sr. Director, Guest Services.

Featured in this story:

• Chris Prelog, President, Windstar Cruises
• Jaymi Fiveash, Sr. Director, Guest Services, Windstar Cruises
• Shahaab Razak, Outbound Sales Manager, Windstar Cruises

The challenge: matching the at-sea experience on shore

Windstar's crew is famous for the experience they create on board. The contact center had to live up to that same standard, often in the very first moments a guest interacts with the brand.

"Our crew performs amazingly. That's why people come back to the ships," Jaymi said. "So we really have to elevate ourselves at the contact center to step up and deliver that same service."

A few specific challenges stood in the way:

• Routine inquiries were absorbing agent capacity. Agents were spending time on simple questions, like a guest asking about a blow dryer in the cabin, instead of the higher-stakes booking conversations where their expertise matters most.
• Building deep destination knowledge across a growing team was hard. Windstar sails to ports most travelers haven't been to, and agents need to speak about those destinations with the confidence of a world traveler.
• Insight into what was actually happening in the contact center was limited. "It's usually the loudest voice, a voice of one," Jaymi said about how feedback typically surfaced.
• Quality management was a sampling exercise. Supervisors were spending hours manually listening to calls and still weren't seeing a holistic picture of how the team was performing.

‍

Windstar needed an AI partner that could automate the routine, elevate the complex, and finally give the team a complete, real-time view of the guest experience.

The solution

Windstar leaned into Cresta as one of the first AI investments the company made, and rolled out a connected suite of products across the contact center:

• Cresta AI Agent handles the high volume of routine chat inquiries, so guests get instant answers and agents only see conversations where they can make a real impact.
• Cresta Agent Assist listens to every call, understands what the guest is asking, and puts the right information at the agent's fingertips in the moment.
• Cresta Insights and AI Analyst give Jaymi and her leadership team a data-driven view of every guest conversation, surfacing trends, identifying coaching opportunities, and feeding decisions across the business.
• Automated Quality Management scores 100% of calls, replacing manual sampling with full visibility into agent performance.

‍

"The contact center is one of the first spaces that Windstar has adopted AI, and we're leaning in hard, and it's really proving to be a great selection," Jaymi said.

Why Cresta

For Chris, the value of Cresta isn't just in the product. It's in how the two companies work together.

"It's not a vendor-customer relationship. This is a partnership," he said. "Technology is evolving. Things are changing all the time, particularly in the contact center space and in the AI industry. You have to lean in. You have to be there. You have to be in front of it, because otherwise you're falling behind."

What's next: the next wave is already in motion

For the Windstar team, the lesson from the first wave of AI is straightforward: in a space that's evolving this fast, hesitation is its own kind of risk. The contact centers that move first are the ones that get to shape what comes next.

Jaymi put it even more simply: "Just jump in. It's time."

That mindset has already paid off. The first wave of AI investments at Windstar reshaped how the contact center operates, what the leadership team can see, and how guests experience the brand from the very first interaction. The next wave is already in motion.