For more than two decades, April Eskelson has built her career around a simple question: what if?
Today, as Vice President of Bold Moves at Jacaruso Enterprises, April sits at the intersection of hospitality, innovation, training, and business development. She has facilitated nearly 500 trainings, influenced more than 3,500 hospitality leaders, and helped bring multiple programs and products to life. But long before she became known for helping organizations think differently, she was simply trying to figure things out herself.
“Looking back at my 23-year-old self walking into the Radisson Hotel Fargo in a tube top and a blazer the day after graduation, I’m still a little shocked they gave me a job.”
Like many hospitality professionals, April learned by doing. She didn’t enter the industry with a carefully mapped-out career plan. What she did have was curiosity, determination, and a willingness to learn.
Early in her career, she became fascinated by the gap between effort and results. Hospitality is filled with talented people who work incredibly hard, yet she often found teams spending valuable time on activities that created motion without creating momentum.
“There was just so much noise, not enough clarity, and way too much time spent on things that didn’t actually drive results.”
That observation would ultimately shape the trajectory of her career.
While others focused on teaching people how to work harder, April became increasingly interested in helping them work smarter. That mindset would eventually lead her into training, instructional design, innovation, AI, business development, and product strategy. Yet no matter how her role evolved, the mission remained the same:
Help people remove barriers, think differently, and perform at their highest level.
Seeing What Others Missed
As April’s hospitality career progressed, she found herself working across hotel sales, leadership, training, and development roles. Regardless of the brand, market, or management company, she kept seeing many of the same challenges.
Talented sales professionals were spending enormous amounts of time searching for information, researching accounts, identifying contacts, and navigating disconnected systems. The work was important, but too often it was getting in the way of the work that mattered most: building relationships, creating trust, and driving revenue.
“I spent years in the trenches, sitting side by side with teams, and I kept seeing the same thing over and over. Good people. Strong effort. But systems and processes making the job harder than it needed to be.”
For many leaders, that observation might have remained a frustration. For April, it became a turning point.
The more teams she worked with, the more she realized the industry’s challenges rarely stemmed from a lack of talent. The opportunity was often hiding in plain sight. Teams didn’t need to work harder. They needed better ways to access information, act on opportunities, and focus on the work that drove results.
That realization sparked a growing interest in training and development. April became increasingly focused on helping people think differently about the work they were doing, not simply teaching them how to do more of it.
It was a shift that would eventually define much of her career.
Teaching Hospitality to Think Differently
Long before AI became a headline and long before innovation became a buzzword, April was helping hospitality professionals rethink the way they worked.
As a facilitator, trainer, and instructional designer, she spent years developing and delivering programs for hotel brands, management companies, ownership groups, and sales teams across the industry. Her focus was never simply sharing information. It was helping people apply it.
Over the years, she facilitated nearly 500 training sessions and influenced more than 3,500 hospitality leaders, building a reputation for turning complex challenges into practical action.
What made her approach different was her ability to meet people where they were. Rather than overwhelming teams with theory, she focused on helping them think differently about the work already sitting in front of them. Whether the topic was sales strategy, leadership development, communication, prospecting, or technology adoption, the goal remained the same: create clarity, build confidence, and help people take action.
Attendees consistently describe her sessions the same way: practical, engaging, and immediately applicable. One participant noted April’s ability to make the content feel “both actionable and relatable,” while another shared that they left with “a new assistant” and a clearer understanding of how AI could help them save time. Those reactions reflect what has become a hallmark of April’s work, helping people move beyond information and into implementation.
Those lessons weren’t coming from a classroom. While working alongside hotel brands, management companies, ownership groups, and sales teams across the industry, April was also helping train, develop, and support Jacaruso’s internal team. The combination gave her a unique perspective. She understood the challenges hospitality leaders were facing because she heard them directly from clients and partners every day. She understood the realities of execution because she was working alongside a team responsible for delivering results.
That experience became invaluable.
Working with hundreds of teams, both inside and outside of Jacaruso, allowed April to identify patterns that extended far beyond a single hotel, brand, or market. She saw where teams struggled. She saw where opportunities were being missed. And she saw how often great results were hiding behind small shifts in thinking.
Many of the ideas that would later shape her work in innovation, product development, and AI were born in those workshops, training sessions, and day-to-day conversations. The more leaders she worked with, the more convinced she became that lasting results don’t come from working harder. They come from removing barriers, focusing on what matters most, and helping people take action.
Today, April is one of the hospitality industry’s most sought-after AI educators, helping hotel teams move beyond theory and put technology into practice. Her workshops continue to challenge assumptions, spark new ideas, and help hospitality professionals rethink prospecting, revenue generation, and the role technology can play in their daily work.
Because for April, learning has never been about collecting information.
It’s about creating momentum.
Why Innovation Became Personal
For many people, innovation starts with technology. For April, it started with observation.
After years of working with hospitality leaders, sales teams, and Jacaruso’s own internal team, she began noticing the same challenges appearing again and again. The brands were different. The markets were different. The people were different. Yet the obstacles were remarkably similar.
Teams were spending too much time searching for information. Sales professionals were manually researching accounts, identifying contacts, tracking opportunities, and piecing together information from multiple sources. Valuable hours were being consumed by administrative work instead of revenue-generating activities.
“I was training sales teams and watching really talented people spend way too much time in the weeds instead of actually selling.”
The more she observed, the more obvious the opportunity became.
The problem wasn’t a lack of effort. It wasn’t a lack of talent. The challenge was that too much time was being spent on tasks that pulled people away from the work that mattered most.
That realization changed the way April thought about innovation.
She was interested in solving problems. If a tool could help people save time, make better decisions, uncover opportunities, or focus on higher-value work, it was worth exploring.
The question that kept resurfacing was simple: why is this harder than it needs to be?
That question would eventually lead her beyond training and instructional design and into the world of product development, innovation, and emerging technology. More importantly, it would position her to help shape some of Jacaruso’s most ambitious initiatives.
Because for April, innovation has never been about replacing people.
It’s about helping people perform at their best.
Turning Ideas Into Action
By 2023, the patterns April had been observing for years were impossible to ignore.
She had spent her career helping teams improve performance, adopt new ideas, and navigate change. But she also recognized that many of hospitality’s biggest challenges couldn’t be solved through training alone. Some required new approaches. Some required new tools. All required a willingness to rethink the status quo.
That mindset led April into a leadership role within Jacaruso Enterprises’ newly formed Innovation Hub, a research and development initiative focused on identifying industry challenges and developing practical solutions to address them.
The move felt like a natural progression. For years, April had been gathering insights from hotel owners, operators, brands, sales teams, and Jacaruso’s own internal team. The Innovation Hub created an opportunity to turn those observations into action.
Working alongside clients, partners, technology experts, and Jacaruso’s internal teams, she became increasingly involved in identifying opportunities, testing ideas, and bringing solutions to life. It was work that combined many of the strengths she had developed throughout her career: listening, problem-solving, facilitation, strategy, and execution.
The experience reinforced something she had long believed: the best innovations don’t start with technology. They start with people.
The more she immersed herself in innovation, the more convinced she became that hospitality didn’t need more complexity. It needed better ways to solve real problems.
Making Innovation Practical
One of the principles that guides Jacaruso Enterprises is simple: do what you love, with people you love, and help others.
That philosophy shaped April’s approach to one of the company’s most successful innovations, Lead Shark.
Originally developed by Jacaruso for internal use, the AI-powered prospecting platform helped sales teams uncover opportunities faster, identify decision-makers, and spend less time searching for information. The results were significant, but what caught April’s attention wasn’t the technology itself. It was the impact.
After years of working with hotel sales teams, she knew the challenges weren’t unique to Jacaruso. Across the industry, talented professionals were spending too much time researching and not enough time building relationships.
Recognizing the opportunity, April worked alongside Jacaruso’s AI Developer and Digital Operations team to help bring Lead Shark to market, giving hoteliers access to the same advantage that had already proven successful internally.
The experience reinforced a belief that has become central to her work: technology should make people better at what they already do well.
That philosophy has also shaped her approach to artificial intelligence. Through workshops, keynote presentations, and client engagements, April has become one of hospitality’s most sought-after AI educators, helping teams move beyond the hype and focus on practical application. Whether she’s speaking on Revenue Hiding in Plain Sight, Prospecting on Easy Mode, or People First, Process Second, Technology Third, her goal remains the same: helping hospitality professionals understand how technology can create more time for the work that matters most.
What makes her approach different is that she focuses less on what AI might do someday and more on what people can do with it today. Attendees frequently describe her sessions as practical, approachable, and immediately useful. One participant shared that April “made AI make sense,” while another praised her ability to customize the training and read the room, ensuring the content connected with the people in it.
Her message is simple.
“If AI is doing relationship-building, you’re using it wrong.”
For April, AI isn’t about replacing people. It’s about removing friction, creating efficiencies, and giving professionals more time to focus on the work that matters most. In an industry built on relationships, that’s where the real opportunity lies.
Why Bold Moves Matters
In September 2025, April stepped into the role of Vice President of Bold Moves at Jacaruso Enterprises, bringing together the many threads that had defined her career: training, innovation, business development, product strategy, and a relentless focus on helping people succeed.
The move wasn’t a departure from her previous work. It was a natural evolution of it.
For years, April had been helping hospitality professionals identify opportunities, solve problems, and adapt to change. Through training and facilitation, she helped people think differently. Through the Innovation Hub, she helped turn ideas into solutions. Through Lead Shark and her work in AI education, she helped bridge the gap between possibility and practical application.
Bold Moves brought those experiences together under one mission: helping hospitality organizations grow.
Today, April spends her time identifying growth opportunities, building strategic partnerships, evaluating new ideas, and helping bring solutions to market. Her approach remains remarkably consistent: start with the problem, listen first, challenge assumptions, and focus on what will create the greatest impact.
It’s a mindset shaped by years of working directly with hospitality professionals and seeing firsthand where opportunities are often missed.
Good ideas are everywhere. Meaningful results are harder to find.
That’s why April believes innovation is only valuable when it creates action. Technology is only valuable when people actually use it. And growth only happens when organizations are willing to move beyond what they’ve always done.
It’s also one of the reasons so many hospitality professionals continue to seek her perspective. She doesn’t stop at identifying possibilities. She helps people put them into practice. As one attendee noted after a recent session, “She made everyone feel comfortable.” Another observed, “She loves what she does, and it shows.”
At its core, that’s what Bold Moves is about.
Not chasing the next shiny object.
Creating opportunities that help people, teams, and organizations move forward.
The Future Belongs to the Curious
Throughout her career, April has built a reputation for asking one simple question: what if?
That question has shaped her work as a trainer, facilitator, innovator, and leader. It’s what led her to challenge assumptions, embrace new technology, and help hospitality professionals rethink how they work.
The hospitality industry will continue to evolve. New tools will emerge. AI will become more sophisticated. But hospitality has always been, and will always be, a relationship business.
Technology can create efficiencies. People create relationships.
Or, as April puts it:
“If AI is doing relationship-building, you’re using it wrong.”
The future doesn’t belong to organizations with the most technology. It belongs to the ones willing to think differently about how they use it.
And it all starts with a simple question:
What if?
