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Osmany Caballero has a diverse work experience spanning multiple industries. Osmany started their career as a Senior Sales Account Executive and Oceania@Home Manager at Oceania Cruises, Inc. In this role, they demonstrated strong networking skills and the ability to close large accounts and complex groups. Osmany then worked as a Sales Coach and Call Center Supervisor at Rauscher Bekke, LLC, where they evaluated and mentored a team of 60 agents and created training manuals and workshops. Caballero later transitioned into the art industry, serving as Manager, Curator, and International Account Manager at Magical Thinking Art. Osmany was responsible for promoting artists' portfolios through various channels and managing gallery inventory. Caballero also co-founded and served as the President of The ComingOutCuba Foundation, where they developed marketing and fundraising strategies and served as a spokesperson and relationship builder. Osmany then worked as a Lead Designer and Owner at InteriorMan Design, where they provided full interior design services. Caballero also gained experience in the furniture industry, working as a Senior Design Consultant and Project Manager at Tui Life Style, a National Sales Manager at ADRIANA HOYOS, and a Senior Design Consultant at Modloft Furniture. Most recently, Caballero worked as the Business Development and Sales Director at Fede Design LLC, a division of Fede Group. Throughout their career, Caballero demonstrated strong leadership, sales, and creative skills.

Osmany Caballero began their education in 2007 at Albizu University - Miami Campus, where they pursued a Bachelor's degree in Business Administration and Management, General. Osmany completed their studies at this institution in 2009. It is also noted that Osmany Caballero later obtained a Bachelor of Business Administration (BBA) degree in Business Administration and Management, General from Albizu University - Miami Campus, although the specific timeframe for this achievement is not provided.