JC

Jason Cavallo

President and Chief Sales Officer

Professional Overview


Jason Cavallo currently holds the positions of President and Chief Sales Officer (Property & Casualty) at Hotaling Insurance Services (HIS). With nearly two decades of experience in the insurance industry, Jason is recognized for his deep expertise in high-level, complex risk mitigation strategies, particularly within the New York construction sector.

Career Path and Professional Experience


Jason Cavallo's career has seen significant progression within Hotaling Insurance Services. Initially serving as Managing Partner and Chief Operating Officer, his leadership and operational expertise led to his promotion. On August 2, 2024, Jason assumed his current roles where he continues to influence the strategic direction and operational efficiency of HIS.

Notable Positions and Roles


  • Founder and CEO overseeing New York’s operations at HIS.

  • Managing Partner & Chief Operating Officer at HIS.

  • President & Chief Sales Officer (Property & Casualty) at HIS since August 2, 2024.


Skills and Specializations


Jason's diverse skill set is particularly honed in the following areas:
  • High-level complex risk mitigation strategies

  • Bespoke risk management/mitigation planning tailored to corporate clients

  • Deep knowledge in the construction insurance domain, backed by the Construction Risk and Insurance Specialist (CRIS) designation


Professional Achievements


  • Holding supervisory and strategic control over HIS’s New York operations.

  • Demonstrated leadership that earned him key promotions within HIS.

  • Extensive experience and proven expertise that have positioned him as a trusted advisor to clients in the NY construction industry.


Professional Affiliations and Online Presence



  • Published several posts about the strategic initiatives and team accomplishments at HIS, showcasing his active involvement in the company’s digital and community presence.


Hotaling Insurance Services Background


  • Hotaling Insurance Services is a family-owned, full-service insurance brokerage firm with nationwide offices across the United States.

  • The company specializes in a variety of insurance services, including Commercial, Private Client, Life Insurance, Employee Benefits, and PEO.

  • They also have niche specializations in sectors like Sports & Entertainment, Construction, Real Estate, Energy, Healthcare Workers, Estate Planning, International, and Bitcoin Mining.


Leadership Structure at Hotaling Insurance Services


  • Bobby Hotaling: Founder

  • Salvatore Alimonda: Partner

  • Dan Dilella: Managing Partner & Chief Growth Officer

  • Vince Castro: Managing Partner

  • Gina Fini: Managing Partner

  • Jason Cavallo: President & Chief Sales Officer (Property & Casualty)

  • Alexa Hotaling: Partner

  • Gabby Dieppa: Managing Partner

  • Neil Verdeja: Managing Partner


Conclusion


Jason Cavallo's extensive experience, coupled with his leadership roles and specialized skills in risk management, positions him as a pivotal figure within Hotaling Insurance Services. His focus on the construction insurance sector and commitment to professional growth reflect his capability and dedication to driving forward the strategic goals of HIS.