Jacaruso Enterprises Appoints Jason Webb as CEO, Launch of AI Platform Planned for 2026

October 31, 2025
Jacaruso Enterprises has appointed Jason Webb as its new CEO, the first leadership change in its 18-year history. Founder Toni Jacaruso will remain as President, and the company plans to launch its AI-powered sales platform, Lead Shark, in 2026.

Jacaruso Enterprises has appointed Jason Webb as Chief Executive Officer, marking its first leadership transition in 18 years, announced in a press release. Founder Toni Jacaruso will continue as President, while Bill Jacaruso remains Chief Operating Officer.

Webb, who joined the company in 2012, has led technology integration initiatives and the development of Lead Shark, an AI-powered sales platform set to launch in 2026. The platform is designed to enhance hotel prospecting by combining artificial intelligence with sales expertise.

Alongside Webb’s appointment, several internal promotions were announced: Janel Allen becomes Senior Vice President of Marketing, Amanda Harris is Vice President of Operations, April Eskelson is Vice President of Bold Moves, and Cheryl Fosberry is Vice President of Sales. Each will contribute to advancing the company’s remote hotel sales services across North America, the Caribbean, and Latin America.

Founded in 2007, Jacaruso Enterprises provides remote hotel sales and training solutions and has been recognized as an Inc. 5000 Fastest-Growing Private Company and an Inc. Best Workplace for three consecutive years.

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