Ole Insurance Group

Ole Insurance Group operates as a digital-first insurer in Latin America, providing financial protection to individuals and families across more than 30 countries through U.S. dollar-denominated life insurance. The company was officially launched in 2022 and is led by CEO and Founder Michael Carricarte. He co-founded the venture with his brothers, Andrew Carricarte, who serves as CTO and President, and Brian Carricarte, the Director of Integration.

The Carricarte family possesses a multi-decade legacy in the Latin American insurance sector. Their journey began in 1986 when they established Amedex, a pioneer in offering international major medical insurance in the region. Bupa later acquired Amedex in 2005. This deep industry experience underpins Ole's strategy, which evolved from the foundation of Amedex, rebranding to renew its image and focus on digital distribution. The firm is headquartered in San Juan, Puerto Rico, and registered in the United States, holding a Class 5 international insurer license. This regulatory status allows it to serve residents of Latin America and the Caribbean while adhering to the standards of the National Association of Insurance Commissioners (NAIC) in the U.S.

Ole's business model centers on simplifying the insurance process. It utilizes a digital platform infused with artificial intelligence for its underwriting, which allows for a streamlined application that can often be completed in minutes without a medical exam for policies up to $1,000,000. The company markets its products primarily through a network of over 4,000 distribution partners. Revenue is generated from the sale of term life insurance policies, which offer flexible terms, fixed premiums, and optional benefits. The firm's financial stability is reinforced through reinsurance partnerships with major global players like RGA, Partner Re, and Munich Re. In January 2025, the company secured $13 million in a Series B funding round led by PayPal Ventures, with participation from Mundi Ventures, AV8, and Advent Morro, to accelerate its expansion and develop new products. Keywords: insurtech Latin America, digital life insurance, dollar-denominated insurance, term life insurance, financial protection, Amedex, Michael Carricarte, Andrew Carricarte, Brian Carricarte, PayPal Ventures, Mundi Ventures, simplified underwriting, AI in insurance, Latin American insurance market, international insurer, family financial planning, insurance distribution partners, digital insurance platform, reinsurance, Puerto Rico insurer