For years, hotel teams have been expected to deliver sales results while juggling operational demands, lean staffing, and ever-changing guest expectations. Sales often become just one more responsibility added to already full plates.

Founded by Toni Jacaruso in 2007, Jacaruso Enterprises was built to change that dynamic. From the start, the focus was simple: provide hotels with experienced, remote sales professionals whose only job is to sell, without pulling attention away from on-property operations. Today, under CEO Jason Webb, Jacaruso remains focused on delivering solutions that help hoteliers work more efficiently and improve profitability.

Business Fortune spoke exclusively with Jason Webb, CEO of Jacaruso Enterprises, Inc., about the company’s origins, its remote sales model, and how Jacaruso continues to support hotels as the sales landscape evolves.

Early on, what did Toni see in traditional hotel sales that made it clear a different approach was needed?

What stood out to Toni early on was that hotel sales wasn’t failing because people didn’t care or weren’t capable, it was failing because the role itself had become unrealistic. Hotels expected salespeople to be everywhere at once: selling, supporting operations, attending meetings, and solving problems. Selling became the thing you did after everything else.

She also questioned the assumption that sales had to live on property to be effective. At the time, that wasn’t a common idea. But Toni saw that what hotels really needed wasn’t more presence, it was more focus. Consistent outreach, follow-up, and relationship-building were getting lost in the day-to-day demands of running a hotel.

Jacaruso built the hotel industry’s first remote sales model, delivering measurable results to thousands of hotels and shaping how many organizations approach remote sales today.

Jacaruso offers a wide range of services. Which of these are the foundation of the business, and how do newer offerings like Lead Shark fit into Jacaruso’s long-term vision?

Remote sales remain the foundation of Jacaruso. From the beginning, the goal has been to give hotels dedicated, experienced sales professionals focused solely on revenue, without adding strain to on-property teams. That model allows hotels to generate demand, build stronger pipelines, and compete effectively, regardless of size, brand, or market.

Everything else we offer is designed to support that same outcome. Hotel Sales Service Plus extends our remote sales model by adding a sales coordinator, while our Hotel Sales Admin Service removes administrative burden so sales teams can stay focused on revenue. Pre-opening sales service helps new hotels enter the market with the right momentum, while interim sales service address staffing gaps or urgent needs. The speaking and training we offer allows us to share practical, real-world insight with hoteliers and translate it into actionable strategies. Each service we offer ties back to improving sales performance and profitability.

Lead Shark, our newest product, is a natural extension of this mission. This AI-powered sales intelligence platform helps hoteliers quickly identify the right decision-makers with verified, up-to-date contact information and account insights in seconds. In an increasingly competitive environment, that speed and accuracy matter more than ever.

With Jacaruso’s sales team working remotely, how do you ensure they stay closely aligned with each hotel’s on-property operations and day-to-day realities?

Remote never means disconnected. Our sales experts work as an extension of the hotel team. That starts with an onboarding kickoff call and continues through consistent, ongoing communication via phone, text, email, video conferencing, and more. Our team works closely with property leadership, revenue management, and operations to understand each hotel’s goals, challenges, and what’s happening on property in real time.

Presence also matters. In addition to the daily remote support we provide, we offer site and market visits and engage directly with key customers when needed. Our sales experts think like hoteliers because many come from on-property leadership roles. They understand service standards and the operational realities that shape the guest experience and drive meaningful results.

Jacaruso has supported thousands of hotels across a wide range of markets and property types. How do you tailor your sales approach for different kinds of hotels, from boutique to branded, luxury to budget, and new openings to established properties?

No two hotels are the same, and we don’t treat them that way. While the fundamentals of selling stay consistent, how we apply them depends on the property, its market, and its goals. Boutique and independent hotels often benefit from strong storytelling, differentiation, and relationship-building, while branded properties focus more on working within brand standards and capturing demand effectively.

Luxury hotels typically require longer sales cycles and high-touch relationships, while budget and select-service hotels prioritize volume, efficiency, and rate integrity. New openings are focused on awareness and pipeline development, while established hotels may be protecting market share or repositioning in a competitive landscape. What never changes is our approach: we take the time to understand the hotel, ownership priorities, and market realities, then tailor sales efforts to fit what that property actually needs.

How does the launch of Lead Shark influence Jacaruso’s growth and longer-term direction?

Lead Shark allows us to support a broader range of hoteliers when remote sales services aren’t the right fit for their current strategy. It gives them better intelligence to stay competitive, strengthen their sales efforts and make smarter decisions. Our growth comes from solving real sales challenges and giving hoteliers tools like Lead Shark that help them move faster, target smarter, and protect revenue.

Beyond Lead Shark, our focus remains on continuing to evolve how we support hotel sales. Innovation comes from investing in our people so they continue delivering results for our partners, refining our sales strategies, and using technology to remove friction from the selling process. Every innovation we pursue is guided by one principle: it must help hoteliers compete more effectively in their markets.

Guiding Jacaruso Enterprises Forward

Jason Webb leads Jacaruso Enterprises after more than two decades working in hospitality. His career began on property, where he gained firsthand experience with the realities hoteliers face every day. Jason has grown with the company through multiple leadership roles, helping expand its hotel portfolio, strengthen its remote sales platform, and advance its digital strategy, including the creation of Lead Shark.

As CEO, Jason is focused on ensuring Jacaruso remains the go-to partner for remote hotel sales. He brings a practical, people-first approach to leadership, grounded in the culture Toni Jacaruso built and focused on results. His role centers on strengthening Jacaruso’s sales services, supporting the people who deliver them, and solving the problems that keep hoteliers up at night.

"Remote sales sit at the heart of Jacaruso’s mission. From day one, the focus has been clear: help hotels become more profitable and competitive, regardless of size, brand, or market.”