For the first time in its 18-year history, Jacaruso Enterprises, the company that pioneered remote hotel sales, has made a historic leadership transition. Jason Webb has been appointed to Chief Executive Officer, becoming the first CEO other than founder Toni Jacaruso, who will continue as President. Bill Jacaruso, will remain as Chief Operating Officer.
The move signals the next chapter for the company that redefined how hotels approach sales. Since 2007, Jacaruso’s remote model has helped thousands of hotels across the U.S., Canada, the Caribbean, and Latin America increase revenue and market share. Under Webb’s leadership, Jacaruso will continue scaling innovation, including the 2026 launch of Lead Shark, its AI-powered sales platform designed to transform hotel prospecting.
Webb is proud to welcome these newly promoted leaders to the executive team:
- Janel Allen, Senior Vice President of Marketing
- Amanda Harris, Vice President of Operations
- April Eskelson, Vice President of Bold Moves
- Cheryl Fosberry, Vice President of Sales
Each brings deep hospitality expertise and a history of delivering measurable results for owners, brands, and operators.
“When I started this company, remote sales was unheard of.", said Toni Jacaruso, President. “Today, Jason and this new leadership team will take us into the next era, leveraging innovation and our people-first culture to help hotels grow stronger and more competitive.”
Since joining Jacaruso in 2012, Webb has spearheaded initiatives that have redefined how Jacaruso delivers results for hotel partners. He was instrumental in integrating technology into the sales process and led the development of Lead Shark, designed to revolutionize hotel prospecting by combining artificial intelligence with proven sales expertise.
“I am honored to step into this role and continue the vision Toni created,” said Jason Webb, CEO. “The hospitality industry moves quickly. We are committed to moving with it by innovating, adopting new tools, and ensuring our team and clients benefit from every advancement. Our goal is to be the first and only call hotels make when they need sales expertise.”
Since its founding in 2007, Jacaruso has been recognized as an Inc. 5000 Fastest-Growing Private Company for several years, and most recently, as an Inc. Best Workplace for three consecutive years. The company continues to innovate while staying true to its founding philosophy: do what you love, with people you love, and help others.
Jacaruso Enterprises is the hospitality industry’s leading provider of remote hotel sales service and training. The company pioneered an affordable and flexible sales outsourcing solution for hotel owners and management companies looking to increase occupancy and revenue. Jacaruso’s customers include small to medium-sized hotels across the U.S., Canada, and Latin America. You can learn more about Jacaruso Enterprises and their remote sales offerings at Jacaruso.com.