One of Toni Jacaruso’s most challenging moments brought Jacaruso Enterprises to life. After more than two decades in hospitality and rising to a senior executive role, she was unexpectedly fired. Days later, that setback became a defining turning point. During a long airport layover, sitting on the floor with a stack of napkins, Toni wrote three lists: what she loved to do, what she liked to do, and what she would never do again. Those reflections became the foundation of Jacaruso Enterprises and its guiding principles: do what you love, with people you love, and help others.

Recognizing a gap in the industry, Toni launched a new model in 2007—remote hotel sales support by professionals who could drive revenue, build relationships, and deliver results without being on property. Her people-first approach has transformed how hotels sell, grow, and connect. Today, the company is a trusted partner to hotels across the U.S., Canada, the Caribbean, and Latin America, empowering hospitality professionals to learn, succeed, and love the work they do.

At Business Honor, we had the privilege of interviewing CEO Jason Webb about how Jacaruso Enterprise’s remote sales model and Lead Shark platform help hotels drive revenue and strengthen client relationships.

How does Jacaruso Enterprises’ model challenge traditional on-property hotel sales methods and redefine how hotels drive revenue?

Jacaruso’s remote sales service model challenges the traditional notion that hotel sales must happen on property. When Toni started the company in 2007, she knew results depended on people, process, and accountability, not location.

The model gives hotels immediate access to experienced sales professionals who act as an extension of their team. These experts handle prospecting, qualify leads, respond to inquiries, and build relationships with corporate and group clients, all while understanding each hotel’s brand, market, and goals.

Hotels benefit by gaining the coverage and expertise of a tenured sales expert at a fraction of the cost, without losing personalization or brand alignment. For many properties, especially limited-service or new openings, it fills a crucial gap, allowing hotel teams to focus on operations while sales remains in expert hands.

 With the right systems, communication, and partnership, remote sales can be as relational and even more effective than traditional methods.

How has Jacaruso adapted its strategies to meet the changing needs of hotels and travelers in today’s market?

The hotel world changes fast. We stay connected to the people we support and focus on what helps their hotels perform. Three years ago, we started using AI internally to replace slow research with fast insight. What used to take hours now takes seconds. It helped our team see market opportunities earlier, understand demand shifts faster, and support our hotels with more clarity. That work led to the development of Lead Shark, our newest intelligence platform launching in 2026. We took what was working for our internal sales team and built a platform around it. Lead Shark uses proprietary AI to show hotels where the real opportunities are, who is behind that business, and how to reach out quickly. It is built by hotel salespeople, for hotel salespeople, and helps teams move faster in a market where timing matters.

What is Lead Shark and how does the tool address evolving challenges facing hospitality professionals and hotels?

Lead Shark is an AI-powered intelligence platform built specifically for hotels. It answers the question most sales teams struggle with: How do we spend less time searching and more time selling? The platform identifies real opportunities in your market, shows you the companies tied to that business, and delivers the exact contacts you should call. In two clicks, you move from insight to outreach. For hotels dealing with smaller teams, shifting demand, and harder-to-reach decision makers, Lead Shark cuts through the noise. Instead of digging through data or guessing who to target, hotels get clear direction, verified contacts, and AI support to help write outreach and prepare proposals. Lead Shark does not replace a salesperson. It removes everything that slows them down.

What features make Lead Shark unique among other lead generation tools available?

Lead Shark is not a generic AI tool. It is built only for hotels. Here is what makes it different:

• No search bar needed: Most tools require you to know exactly who you want to research. Lead Shark gives you the opportunities up front. 

• Two clicks from insight to action: You log in. You see your market. You click the opportunity. You click the contact. That’s it. 

• Built-in AI designed for hotel sales: The Lead Assistant helps you write emails, phone scripts, follow up messages, proposals, and segment-specific outreach. It focuses on revenue generating tasks.

• Hotel-specific market intelligence: The platform looks at your market, your comp set, and your demand patterns to identify the business that fits your hotel.

The result is simple: Hotels spend less time researching and more time talking to the people who can book with them.

How does Jacaruso Enterprises ensure that each hotel receives personalized attention and tailored strategies to meet its specific market needs?

Every hotel is unique, and we treat it that way. From the start, we learn each property’s story, team, goals, and market challenges because sales requires a tailored approach.

Each hotel is paired with a sales expert who acts as an extension of the on-property team, building relationships, understanding the market, and creating a plan aligned with the property’s goals. The broader Jacaruso team supports them with insights, best practices, and market data to drive faster results.

We use data tools like Lead Shark to analyze trends, identify opportunities, and prioritize the right leads. Combining AI intelligence with our sales expertise ensures each hotel gets a targeted, actionable strategy for its market.

Personalized attention isn’t just a feature; it’s our foundation, ensuring every hotel feels supported, understood, and confident in its sales strategy.

In what ways does Jacaruso Enterprises’ training prepare tomorrow’s hospitality leaders to deliver exceptional guest service and enhance overall profitability?

We believe great sales start with great people, so training is core to what we do. Our programs develop confident professionals who grow revenue, strengthen relationships, and elevate guest experiences.

We focus on real-world skills, not theory. Every module reflects what our sales professionals do daily—prospecting, responding to leads, building partnerships, and turning relationships into results—so teams can apply learning immediately and see measurable impact.

Training also develops leadership, helping participants see how sales drives guest experience and hotel success. Through virtual learning, live coaching, and feedback, we teach future leaders to think strategically, lead with empathy, and deliver results.

Ultimately, we help hospitality professionals become more confident, capable, and connected to their purpose, shaping the next generation of industry leaders.

What makes the Jacaruso Account Network a powerful resource for both your team and your hotel partners?

The Jacaruso Account Network (JAN) connects travelers with over 800 hotels nationwide, helping hotel partners unlock new business opportunities and strengthen market relationships.

JAN provides sales professionals visibility into travel patterns and account activity across industries, enabling quick identification of trends and opportunities that benefit hotels. While we don’t share proprietary info, this approach gives partners a competitive advantage by acting fast on shifts in demand.

For our team, JAN fosters alignment and collaboration, keeping sales professionals informed and supported remotely. For hotels, it expands access to new business and leverages the collective expertise of a nationwide sales team.

JAN provides hotels with the reach, perspective, and resources they need to grow business and build stronger connections with travelers.

Jacaruso Enterprises continues to redefine hospitality sales by combining expertise, innovation, and a people-first approach. With its remote model and Lead Shark platform, the company empowers hotels to maximize revenue, strengthen client relationships, and stay ahead in a rapidly evolving market.

Toni Jacaruso - Founder and President & Jason Webb - CEO

Jacaruso Enterprises was founded by Toni Jacaruso, whose vision still guides everything we do. As Founder and President, she mentors leaders, shapes strategy, and ensures our values remain central. Her entrepreneurial, people-first mindset built a company thriving on innovation, connection, and trust.

CEO Jason Webb shares that commitment to people, purpose, and performance. With decades of hospitality and sales experience, he develops teams that deliver results, expands our reach, and drives technology like Lead Shark.

Together, Toni and Jason lead with authenticity and collaboration, keeping Jacaruso grounded in its values while driving growth for our hotels.

"Jacaruso empowers hospitality professionals to grow, succeed, and thrive in an ever-changing industry. The company guides hotels toward focused revenue growth through expert support and precise market data."