# Michael Carricarte

> Michael Carricarte is the Miami-based co-founder and chief executive of Olé Life, a digital insurer serving Latin America and the Caribbean. A second-generation insurance entrepreneur, he led Amedex and USA Medical Services, held senior roles at Bupa and Pan-American Life Insurance Group, and later founded Olé with his brothers Andrew and Brian. His career combines regional insurance experience, technology-led distribution, and a longstanding record of community work in Miami.

- **Role:** Co-founder and Chief Executive Officer at Olé Life
- **Organizations:** Olé Life, Amedex, USA Medical Services, Bupa, Pan-American Life Insurance Group
- **Education:** Owner/President Management Program, Harvard Business School
- **Known for:** Built and led insurance businesses that collectively served more than one million customers across 42 countries before their acquisition by Bupa., Launched Olé Life as a fully digital life-insurance carrier serving Latin America and the Caribbean., Raised a $12 million Series A in 2023 and a $13 million Series B led by PayPal Ventures in 2025.

## Career timeline

- **1986** — Began his career in the Carricarte family's Latin American insurance businesses, including Amedex and USA Medical Services.
- **1997** — As president of Amedex, was recognized in the US Congressional Record for leading a building-fund effort that added classrooms and a playground at St. Francis Xavier School in Miami.
- **2001-2003** — Completed Harvard Business School's Owner/President Management Program.
- **2005** — Amedex and USA Medical Services were acquired by Bupa; the businesses had served more than one million customers in 42 countries.
- **2010** — Became president of Pan-American Life Insurance Group's International Private Client division.
- **2019** — Founded the company that became Olé Insurance Group.
- **2022** — Launched Olé Life with brothers Andrew and Brian as a fully digital life-insurance carrier for Latin America.
- **2023** — Olé raised a $12 million Series A; the company reported close to $1 billion in issued coverage and members in 30 countries.
- **2025** — Olé raised a $13 million Series B led by PayPal Ventures and entered a reinsurance partnership with Swiss Re.
- **2026** — Olé expanded in Brazil and advanced a partnership-led entry in Mexico.

## Achievements

- Built and led insurance businesses that collectively served more than one million customers across 42 countries before their acquisition by Bupa.
- Launched Olé Life as a fully digital life-insurance carrier serving Latin America and the Caribbean.
- Raised a $12 million Series A in 2023 and a $13 million Series B led by PayPal Ventures in 2025.
- Secured reinsurance support that includes Swiss Re, RGA, PartnerRe and Munich Re.
- Received International Investor's 2025 Most Innovative CEO - Insurance, LATAM award.
- Led a community fundraising effort that delivered new classrooms and a playground for St. Francis Xavier School in Miami in 1997.

## Latest updates

- **2026-09** — Visited Mexico for adviser training and the public launch of Olé's alliance with Seguros Patrimonial.
- **2026-08** — Discussed Olé's plan to reach Mexico's emerging middle class through more accessible digital life insurance.
- **2026-04** — Outlined Olé's Brazil strategy, built around US-dollar-denominated coverage distributed through a partnership with Nomad.
- **2026-03** — Olé entered Brazil as part of its broader expansion across Latin America.
- **2025-05** — Announced Swiss Re as a key reinsurance partner alongside Olé's existing global reinsurers.
- **2025-01** — Closed a $13 million Series B led by PayPal Ventures with participation from Mundi Ventures, AV8 and Advent Morro.

## Links

- Website: https://olelife.com
- LinkedIn: https://www.linkedin.com/in/michael-carricarte-9b4abb211
- Facebook: https://www.facebook.com/OleLife

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Profile page: https://yespress.io/michael-carricarte
Published by YesPress — https://yespress.io
Last updated: 2026-09-27