Jorge de la Osa

Director, Legal Recruiting & Placement

Jorge is Director of Legal Recruiting & Placement, working in the company’s Tampa office.

As Director of Legal Recruiting & Placement, Jorge serves the Tampa Bay legal community by connecting top-tier attorneys with meaningful flexible engagements and permanent roles, helping legal departments and law firms swiftly meet fluctuating demand.

Jorge brings extensive experience leading legal teams across real estate, hospitality, and resort vacation ownership industries. Most recently, he served as Executive Vice President, Chief Legal and Compliance Officer, with Bluegreen Vacations in Boca Raton, managing a 20-associate legal department and successfully navigating a $1.5 billion sale to Hilton Grand Vacations.

Previously, Jorge held the role of Executive Vice President, General Counsel at Wyndham Vacation Ownership in Orlando, leading 80 associates in the U.S. and Australia. During his eight-year tenure, he focused on development, compliance, regulatory affairs, consumer finance services, and negotiated a spin-off transaction from Wyndham Worldwide.

Jorge began his legal career as a real estate associate at BakerHostetler LLP in Orlando, counseling vacation ownership companies like Hyatt, Disney, and Starwood on hospitality, resort development, and timeshare law. He earned his J.D. from the University of Florida Frederic G. Levin College of Law and a B.S. in Business Administration from the University of Florida.

A former board member of Harbor House of Central Florida and volunteer with Big Brothers Big Sisters of Central Florida. Jorge and his wife Ada have three sons and live in Treasure Island, Florida, with their dog Scout. Jorge enjoys endurance sports such as triathlons and marathons.

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