Jason Webb, Jacaruso CEO: “The industry moves quickly. We are committed to moving with it by innovating, integrating new tools, and ensuring our team and clients benefit from every advancement.”

In 2007, Toni Jacaruso saw a blind spot in hospitality that no one was addressing. Hotels without a dedicated sales professional were leaving revenue on the table. For hotels in certain markets or during staff transitions, recruiting top talent locally was a challenge, and the cost of hiring full-time sales teams was out of reach. Her solution: build a team of sales professionals who could work remotely, bringing seasoned sales expertise and proven strategies to any property, anywhere so they can lead the market. What began as an idea scribbled on an American Airlines napkin became Jacaruso Enterprises, a company that redefined hotel sales. This solution wasn’t just clever, it was accessible to any hotel anywhere and disruptive to the industry. Remote sales service gave both branded and independent hotels a chance to compete and it delivers results quickly. Over the years, the remote sales model has become the blueprint for countless sales organizations and has influenced how many brands approach remote sales today. Toni’s vision laid the groundwork for this shift, opening the door for others to design and implement strategies of their own.

By the time Jason Webb joined the company in 2012, the model had already proven its worth. The company scaled quickly, rooted in a philosophy that continues to shape its culture today: do what you love, with people you love, and help others. Managing a portfolio of 10–15 hotels in his early days at Jacaruso, Jason’s natural charisma, strong sales instincts, and ability to connect with people quickly earned him a promotion to Senior Director of Sales. In that role, he led a high-performing team and helped expand Jacaruso’s hotel portfolio through a key partnership with a major hotel brand. From there, he advanced to Vice President of Sales Operations, overseeing the entire sales team and driving company-wide growth. Most recently, as Vice President of Digital Operations Jason brought the same scrappiness and innovation to advancing Jacaruso’s digital strategy before stepping into his new role as CEO in October 2025.

What sets Jacaruso apart is that every member of its executive team shares the same sales DNA. Each began as a Regional Director of Sales, carrying firsthand experience of managing portfolios, navigating stakeholder relationships, and tackling industry challenges head-on. That shared background keeps the company grounded in what sales teams really need and fuels its commitment to making their jobs easier while delivering better results for partners. Jacaruso strives to be the go-to name in hotel sales by combining talent, technology, and culture. Under Jason’s leadership, this approach centers on three commitments—delivering measurable results, creating smarter sales strategies, and keeping people at the heart of the business.

Today, Jacaruso offers a wide spectrum of services that address the evolving needs of hotels, management companies, brands, and ownership groups. Its flagship Remote Hotel Sales Service gives properties immediate access to best-in-class professionals who can stabilize operations, build a sales pipeline, and drive revenue growth. For hotels in transition, preparing to open, undergoing renovations, or recovering from natural disasters, Jacaruso adapts its services to meet the moment. Flexibility and customization are built into the model, ensuring every solution aligns with the unique challenges of each property.

Their newest service, Lead Shark was developed based on the firsthand experience of Jacaruso’s Regional Directors of Sales. Currently in pilot, Lead Shark conducts market research, analyzes trends, tracks competitors, and qualifies leads. It combines Jacaruso’s proven sales expertise with artificial intelligence to take the grind out of research and prospecting, letting salespeople focus on closing business. The public rollout is slated for 2026 and marks another bold step in blending human expertise with artificial intelligence.

Jacaruso’s impact to the industry isn’t limited to it’s services. It invests in people through speaking engagements, tailored training, and a free online hospitality community where they share resources to help hotels win. That commitment to growth—for clients and for the industry—has made Jacaruso more than a remote sales vendor. They have become a trusted sales partner for thousands of hotels.

Nearly two decades after its founding, Jacaruso Enterprises has stayed true to Toni’s original vision. They remain committed to their passion of hotel sales, innovation, and helping hotels thrive.

In conversation with Jason Webb, new CEO of Jacaruso

Jacaruso pioneered remote hotel sales support. What challenges did this model address, and how has it evolved over time?

The original challenge that the remote sales model addressed was access. Many hotels lacked local top-tier sales talent or couldn’t afford it. Our model removes that barrier, giving any property, anywhere, the expertise it needs to lead their market.

When we first launched, many were skeptical about remote sales. They did not understand how our team could access brand systems, send contracts, respond to leads, be productive, and fully support a hotel without being on site. Technology has made this possible and has become one of our greatest advantages. We use a highly customized Salesforce CRM to access and deliver results through dynamic, interactive reporting.

In my previous role as Vice President of Digital Operations, I led our first big automation for Salesforce to deliver market data to our team without hours of manual research. That laid the groundwork for my development of Lead Shark that combines market intelligence, competitor tracking, and contact data into a single workflow, allowing us to move from identifying an opportunity to speaking with the decision-maker in record time. This gives Jacaruso a distinct advantage in closing business faster and driving results for our partners. It’s something we think is so powerful we want to share it with the world.

The greatest challenge now is staying ahead of the technology curve. The industry moves quickly, and we are committed to moving with it by innovating, integrating new tools, and ensuring our team and clients benefit from every advancement.

How does Jacaruso ensure high-impact results during transitional periods?

We deliver high-impact results by springing into action quickly, deliberately, and with our team’s expertise at the center. Within days of onboarding a new hotel, we complete a market assessment, identify high-value opportunities, and begin targeted outreach. Our sales experts know exactly what to look for, and our custom technology surfaces the right prospects instantly. Our sales experts then turn those insights into booked business. By combining the skill and strategy of our team with AI-powered intelligence, we generate revenue even during challenging or low demand periods.

How does your training empower hospitality leaders and staff?

The foundational vision of Jacaruso is to do what you love, with people you love, and help others. We freely share our expertise to help others with training built for real-world results that actually move the needle.

Our training empowers hospitality leaders and staff with practical, actionable skills they can apply immediately. We teach them how to analyze markets, handle rate objections, close more business, and optimize operations. Beyond sales, we strengthen teams in service, lead generation, team building, marketing, operations, culture, and leadership, helping them perform confidently, make smarter decisions, and thrive in any market or situation.

Our team is incredibly seasoned. We’ve seen it all and know how to help people succeed. Each session is customizable, ensuring the content aligns with the unique needs and challenges of every team.

What do you look for in building such a high-performing team?

For us, building a high-performing team starts with the right people. We look for individuals who are curious, scrappy, and relentless in pursuit of results. Experience matters but attitude and problem-solving ability matter more. We want team members who embrace collaboration, thrive in fast-paced environments, and care deeply about our clients’ success.

Culture and alignment are just as important. Everyone on our team understands our mission, vision, our values, and how their work contributes to the bigger picture. Continuous learning and adaptability are also non-negotiable as we evolve, expand our service offerings, and continually refine our approach.

Our team is truly unique. I’m sure a lot of CEOs say that, but each and every person at Jacaruso brings a combination of expertise, creativity, and dedication that’s rare in this industry. That mix is what allows us to move quickly, execute with precision, and consistently deliver exceptional results for hotels. We’ve been recognized by Inc. 5000 as a Best Place to Work for the last three consecutive years, and it’s because of our amazing team who show up every day. They are the driving force behind our success.

How does Hotel Sales Support Services PLUS help clients grow?

Our Hotel Sales Service PLUS provides hoteliers with a full sales engine. It combines proactive strategy led by an assigned Regional Director of Sales with behind-the-scenes support from a Sales Coordinator, giving hotels two sales experts who manage every aspect of the sales process efficiently. This service helps hotels streamline operations, capture and respond to more leads, and execute targeted strategies to increase bookings and drive revenue growth. It’s ideal for properties with high lead volumes, operational challenges, or a need for additional support with sales administrative duties.

How does your JE Community foster collaboration and innovation?

JE Community is a space for hospitality professionals to connect, share knowledge, and access resources. We’re committed to sharing best practices, strategies, and real-world solutions that we encounter every day with others in the space. This constant exchange of insights keeps both our clients and community members with the information they can use to compete

What does the future hold?

The future of Jacaruso is about continuing to innovate and lead in hospitality sales. We’re committed to being the premier partner for hotel sales services, delivering unmatched expertise, and result-driven solutions that clients can trust. Our ambition for this extends beyond North America. We’re striving to be the global leader in hotel sales solutions, setting the gold standard in diversified products and services while preserving our culture and employee satisfaction. We aim to ensure our team members thrive as much as our clients do.

So, what’s next for us?

One of our biggest upcoming initiatives is the public launch of Lead Shark, our AI-powered platform, in 2026. Lead Shark will transform how hoteliers approach sales, integrate market intelligence, lead qualification, competitor insights, and more into a single, seamless tool. We believe it will be a game-changer, helping hotels move faster and drive measurable revenue growth. Beyond technology, we’re continually expanding our services and training programs to ensure Jacaruso remains at the forefront of innovation in the hospitality sales worldwide.

Meet the new CEO of Jacaruso

Jason Webb brings over 20 years of hospitality experience to his new role of CEO. He is the first CEO other than the owner and President, Toni Jacaruso. Since joining the Jacaruso team in 2012, Jason has led initiatives that have transformed Jacaruso’s services, culture, and technology. Jason’s leadership style is collaborative, strategic, and results focused. He’s passionate about building great teams, creating lasting solutions, and helping Jacaruso’s hotel partners succeed. With company culture at the forefront, his proven ability to integrate technology with the sales process continues to give Jacaruso a clear competitive edge.

For Jason, Jacaruso’s future is about more than growth. “We want to be the first and only call hotels make when they need sales expertise,” he says. “That means delivering faster, smarter, and more effective solutions than anyone else.” With technology at the center, human expertise driving strategy, and culture at the center, Jason’s leadership ensures Jacaruso continues to be the name synonymous with hotel sales.

A Kiwi by birth and a Texan by choice, Jason enjoys the outdoors, traveling, and adventures with his wife and two daughters. He approaches his work at JE with that same adventurous spirit, creativity, and a drive to move forward.

“We ensure high-impact results by springing into action quickly, deliberately, and with our team’s expertise at the center.”