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How Visit Milwaukee and San Francisco Travel Add a Human Touch to AI

LeRoy Butler poses in front of a Milwaukee mural for Ask LeRoy. Credit: Visit Milwaukee

The epochal launch of ChatGPT in November 2022 catapulted the world into a new digital era, with artificial intelligence at its core. ChatGPT shattered user adoption and usage records, becoming the fastest-growing consumer application in history. Three years on, the chatbot sees 700 million users every week—and that’s just one platform.

While just as eager to adopt AI, companies and associations have taken a more cautious approach, integrating AI into their practices and policies over time and analyzing how it can impact their image, message, productivity and performance.

The 2025 DestinationNEXT Futures Study—a global survey released every other year by Destinations International (DI) in partnership with MMGY NextFactor—researched how AI is impacting destination marketing organizations (DMOs) in particular and discovered that “the foundations of destination marketing are being profoundly reshaped” largely due to generative AI.

But the report also noted that “at the same time, authenticity is more valuable than ever, as travelers seek real, human-centered experiences and stories they can trust.”

There’s a fine line for DMOs to walk as they figure out how to balance the benefits of AI with something technology can’t replicate: the human touch. Here’s how two DMOs—Visit Milwaukee and San Francisco Travel—are thoughtfully embracing AI and authentically reimagining their destination marketing efforts.

[Related: How Visit KC and VisitNorfolk Are Balancing AI With Authenticity]

Visit Milwaukee

LeRoy Butler inside the Baird Center. Credit: Visit Milwaukee
LeRoy Butler inside the Baird Center. Credit: Visit Milwaukee

The people who know Milwaukee best are at the center of Visit Milwaukee’s marketing efforts, too, and like many other DMOs navigating the age of AI, Visit Milwaukee has introduced a chatbot-like concept for people looking to learn more about the destination.

Except instead of chatting with a bot, users will chat with Visit Milwaukee’s AI-powered augmented reality (AR) sales representative, who appears as a lifelike 3D avatar of Pro Football Hall of Famer LeRoy Butler.  

“The idea came about during the time of the [2025] NFL Draft being hosted in nearby Green Bay,” said Josh Albrecht, chief marketing officer at Visit Milwaukee. “We wanted to find ways that we could engage with fans when they were arriving and traveling through Milwaukee to that big event, and having a legendary [NFL] Packer be a part of the messaging was important to us. But since we aren’t home to the Packers, we’re a neighbor, we were like, ‘How can we make it more authentic to Milwaukee?’”

The Visit Milwaukee team looked into former players who are making an impact in the city, and LeRoy Butler’s name came up.  The “full-fledged Milwaukee resident” has called the city home for years after his playing career and is active in the community.

“We thought it’d be perfect to work with him during our promotions around the NFL Draft and have him be one of Milwaukee’s sports ambassadors,” Albrecht said. “And when we met with him, he happened to mention that he was working on an AI project for literacy and working with schoolchildren.  I thought, ‘Wow, that sounds really cool. I wonder if there’s a way we can incorporate that with travelers and meeting planners?’”

"Ask LeRoy" AI-powered augmented reality (AR) platform. Credit: Visit Milwaukee
"Ask LeRoy" AI-powered augmented reality (AR) platform. Credit: Visit Milwaukee

And with Butler’s help, Visit Milwaukee found a way. The DMO worked with the team Butler had already put together for his AI-related project to build its own version of Butler as a virtual sales rep. Butler recorded himself answering some starter questions for Visit Milwaukee, and from there, AI was able to learn his voice to incorporate it into additional responses later on.

“Part of what we wanted was to truly represent him as a person, who could also truly represent the destination,” Albrecht said. “So there are places vetted by him, places he would recommend. We made sure to include things that were his go-to spots because we wanted it to be his experience as well, and for people to learn from that.”

“Ask LeRoy” made its debut in late August at the Connect Marketplace show in Miami. One week later, the Meetings Today team had a chance to experience the AI-powered AR sales representative for themselves during a happy hour with Visit Milwaukee, and where Butler himself made an appearance.  

“Ask LeRoy” works by inviting users to scan a QR code with a phone, and Butler appears on screen looking as though he’s standing in the room with you. The avatar greets guests, highlights the city’s meetings and conventions scene and answers questions about the Baird Center, hotels, venues, restaurants, attractions and more.

“It’s been very well received. People have a lot of fun engaging with the AI-version of LeRoy—along with the live version, who came with us to Connect Marketplace,” Albrecht said. “People really appreciate the novelty of it. It’s not just a chatbot to get you information, but truly a way to get information through an experience that leaves an impression on you.”

[Related: Geopolitics, Tech and Community Input Impacting DMOs]

San Francisco Travel

“AI has quickly moved from an experimental phase in destination marketing to a key tool being utilized by DMOs across the country,” said Lynn Bruni-Perkins, executive vice president and chief marketing officer of San Francisco Travel. “Most DMOs recognize the need to embrace AI as traveler behavior evolves and see it as an opportunity to create operational efficiency while providing visitors and clients with more personalized experiences.”

The SF Travel marketing team uses generative AI primarily to brainstorm content ideas, social media campaigns and trip inspiration, as well as for the conversational chatbot on the SF Travel website, sftravel.com, that functions as a virtual visitor guide/concierge. From a productivity perspective, the benefits of AI can’t be denied.

Lynn Bruni-Perkins. Credit: San Francisco Travel Association
Lynn Bruni-Perkins. Credit: San Francisco Travel Association

“We are a small team, so AI has enabled us to maintain a larger content footprint,” Bruni-Perkins said, though they’re careful not to let efficiency cloud credibility. “Our team is consistently monitoring and editing AI outputs to ensure they are both accurate and authentic…If we misrepresent the city, we undermine our credibility and break the trust of our audiences.”

SF Travel understands the risk that comes with using AI to increase efficiency and makes sure audience and accuracy are prioritized above all else. The DMO recently updated its AI chatbot to provide suggestions based on what each individual user is specifically seeking, enhancing personalization while delivering reliable results.  

“In my opinion, DMOs should not avoid the use of AI, but need to consistently monitor and edit its outputs to ensure accuracy and authenticity,” Bruni-Perkins said. “In content and marketing, they should be careful about representing specific communities—AI can support content creation, but it shouldn’t replace the real voices of the community.

“As the DNext study suggests, we are constantly curating and amplifying compelling stories from visitors and locals to enhance our storytelling, primarily through social media,” she added. “We amplify stories that align with our brand pillars—iconic SF, diversity, arts and culture, and culinary—and that represent diverse voices.”

SF Travel embraced these pillars in its “Heart of the City” video series, which highlights San Francisco’s diverse neighborhoods “through the eyes, the work and the experiences of the locals who live in them,” Bruni-Perkins said.

“The content was 100% driven by local residents and helped create the story of each neighborhood through their lenses. It has resonated deeply with both visitors and locals alike,” she continued. “And locals and visitors can be our greatest, authentic storytellers about what makes San Francisco a unique and compelling place to be.” 

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Taylor Smith | Content Manager, Destinations

Taylor Smith joined Meetings Today magazine in May 2022 as a content developer, destinations and features and is the face behind the publication's column, "The Z: Planning for the Industry's Next Generation," which explores how to welcome, work with, understand and plan for the industry’s next wave of professionals, Gen Z. In addition to writing about the meetings and events industry’s newest and youngest members, Smith also covers top and trending meetings destinations as well as topics including wellness, sustainability, incentives, new and renovated properties and industry trends for Meetings Today.

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