Hospitality leadership is rarely shaped in a quiet office. It emerges in the middle of real days, real guests, and real constraints. It is formed by watching what actually works, what breaks under pressure, and what teams can sustain when the pace does not let up.
As Vice President of Sales at Jacaruso Enterprises Inc., Cheryl Fosberry brings a perspective formed by experience across varied markets, hotel types, and ownership models. For Cheryl, that grounding is the foundation of how she leads and how she approaches sales, focusing on clear priorities and strategies built for the specific hotel in front of her.
Her philosophy is straightforward. Sales is not about chasing everything. It is about building a plan that fits the property, supports the people executing it, and stays consistent long enough to create momentum.
Scooping Ice Cream Shaped Her Leadership Style
Cheryl’s leadership story started well before she ever stepped into a hotel. “If you go far enough back, my first job was scooping ice cream,” she said.
Her early experience in food and beverage and sales taught her about what really matters in hospitality: what good service feels like from the customer side. Guests do not remember your intentions; they remember their experience. Those early lessons shaped how she thinks about leadership. She learned to value empathy, responsiveness, and making sure the plan supports the people doing the work.
When Cheryl’s career moved into hotels, she started at a large resort with multiple lodging types, restaurants, recreation, and constant guest needs. Her role touched just about everything. The fast-paced, complex environment gave her a deep respect for operations and for how interconnected hotel teams really are. She learned that to be effective, sales cannot ignore what is happening across the property.
Later, she worked in smaller, leaner hotels. In those environments, sales had to be focused and disciplined. Seeing both ends of the spectrum helped her develop a practical, actionable leadership style. “I try to lead with perspective,” she explained. “I stay grounded in what teams can realistically execute day to day. I focus on strategies that support people, rather than overwhelm them.”
Sales Strategy Has to Start with Context
Over the years, Cheryl has worked across a wide range of hotel brands and ownership structures. That breadth reinforced a truth she comes back to often. No two hotels are the same, even when they share a flag. Priorities shift for any individual property based on ownership goals, asset type, market conditions, and what the team can sustain.
“I do not believe in starting with a template. I believe in starting with context,” she said. It involves first considering a set of practical questions. What is ownership trying to accomplish? How is the property positioned in the market? What demand actually exists? What can the team execute consistently?
Cheryl has proven the effectiveness of sales strategy built around those factors. Focusing on the right priorities helps keep sales from feeling like pressure layered onto an already busy operation. Creating a clear strategy based on reality means it is a strategy the team can actually execute on to deliver results.
Relationships and Consistency Still Win in Sales
Technology changes. Markets shift. Tools evolve. Cheryl knows that the fundamentals remain consistent.
“Sales is much more about relationships than scripts,” she said.
Her experience shows that strong outcomes rarely come from saying the perfect thing. They come from listening closely, asking thoughtful questions, understanding what someone truly needs, and being honest about what will and will not work. It is an approach that builds trust, trust that leads to repeat business and long-standing partnerships.
Cheryl also understands that consistency is key to results. “I learned, sometimes the hard way, that consistency matters more than intensity,” she said. Sales rarely breaks down because a team is not working hard. It breaks when attention is scattered, follow-through drops, or priorities change too often.
She explained that sustainable performance comes from doing the fundamentals well, day after day, especially when the market shifts or when the operation is stretched. Quick wins can be energizing, but long-range success develops through trust and consistent execution.
What Sets High Performing Hotels Apart
Across markets and brands, Cheryl has observed repeating patterns. Hotels that outperform their comp set tend to be very clear about who they are and where they focus. They know which segments matter most. They say no to business that does not fit. They align sales and operations around a shared set of priorities. “You can feel that clarity when you walk the property,” she explained.
Hotels that struggle often demonstrate the opposite pattern. They try to be everything to everyone. They shift direction too frequently. They ask teams to execute plans that do not match staffing levels or market conditions. “What separates the two is focus and follow through,” Cheryl said.
In high performing hotels, sales and operations meet regularly. Goals are defined and achievable. Teams understand not just what they are selling, but why it matters. This alignment creates confidence and improves performance, even in challenging markets.
Why Sales Is Not a Short-Term Fix
One of the messages Cheryl repeats most often is also one of the most difficult to practice under pressure. “Sales is not a quick fix,” she said. “It is a long-term investment that requires consistency, patience, and support.”
She understands why leaders want immediate results. Hotels do not always have the luxury of waiting. But she has also seen what happens when sales is treated like something to turn on and off in response to short-term dips. It rarely delivers sustainable outcomes.
The hotels that see the strongest results stay committed, give teams the tools and direction they need, and allow the strategy time to work. When ownership, leadership, and the hotel team are aligned and playing the long game, performance becomes more predictable and far more resilient.
What Partnership Looks Like at Jacaruso
Cheryl was drawn to Jacaruso because the company is grounded in the realities of hotel operations and sales. “This is a team built by people who have actually sat in the sales chair,” she said.
Jacaruso is led and sustained by people who understand what it feels like to be responsible for results without perfect resources.
The company is known in the industry for pioneering remote hotel sales as an affordable and flexible model for owners and management companies seeking sales expertise. Supporting hotels across a wide range of brands and markets, its remote sales services help hotels build relationships and drive results in practical ways.
Cheryl describes the work as partnership, not a one-size-fits-all solution. Some hotels need help rebuilding a foundation after turnover or disruption. Others need sharper segmentation, stronger account management, or more proactive outreach. The approach is designed to adjust based on what will be most effective for that specific property. “We start by listening,” she said. “Our approach is intentionally flexible.”
When Cheryl and her team step into a hotel, they frequently come across competing priorities. Ownership wants performance. Operations wants stability. Sales teams are stretched thin and reacting to whatever feels most urgent. Her role is to bring clarity, reduce noise, and help hotels narrow in on the few priorities that will most drive revenue. Then the on-site and remote teams can spend their time building real relationships with guests and accounts.
Cheryl says there is a clear distinction between Jacaruso and other hotel sales options in the market. “Many third-party sales options promise activity. What is harder to find is judgment,” she said.
For her, the value does not lie only in how much work is completed. It is the decisions a hotel is supported in making through the work. Knowing when to push, when to pause, and when to change direction matters just as much as effort. The right discernment comes from experience, pattern recognition, and a commitment to results that last.
Turning Strategy into Execution
Cheryl remains optimistic about the future of hospitality sales, even as hotels face tighter margins, leaner teams, and increasing complexity. She believes the leaders who win will be the ones who protect focus, support their teams, and stay disciplined long enough for momentum to build.
What excites her most is the opportunity to keep raising expectations for what sales support can look like, not by adding noise, but by making strategy executable.
Looking ahead, she is energized by how Jacaruso continues to help hotels drive revenue in ways that make sense for their teams, their markets, and their long term success.
