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Ole Insurance Group

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An easy, fast and flexible life insurance. Without medical exams for policies up to 1 million dollars

San Juan, Puerto RicoFounded 2021Fintech
Valuation $0–100M Latest valuation · 2025
Headcount 100–500 Current team size
Total funding $10–50M Disclosed equity funding
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About 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.

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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

Source: Dealroom company data

At a glance

Status
Operational
Founded
2021
Headquarters
San Juan, Puerto Rico
Employees
124
Open positions
1
Dealroom signal
83.5/100
Industry
Fintech
Sub-industry
Insurance
Sector
Fintech, Challenger Insurance, Life Insurance, LandH Insurance
Client focus
b2b, b2c

Latest news

Press, funding announcements and product moves mentioning Ole Insurance Group.

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Funding history

3 recorded events

Company financing events and reported valuations.

Deal typeDateAmountValuationInvestorsSource
SERIES BEquity / VC Jan 2025 $13M $52M AV8 Ventures · Advent-Morro Equity Partners · Mundi Ventures · PayPal Ventures
SERIES AEquity / VC Jun 2023 $12M $48M Mundi Ventures · Morro Ventures · AV8 Ventures
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Growth signals

Ole Insurance Group website traffic

Latest recorded traffic for Ole Insurance Group is 4.1K monthly website visits, down 48.1% over the last three months. Ole Insurance Group's team grew 8.8% over the past year.

Latest monthly visits4.1K 3-month web change-48.1% 1-year team growth+8.8%
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Similar companies

Closest operating peers by Dealroom taxonomy

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Investors

6 investors on the cap table

From Dealroom's funding and investor records, grouped by the round each investor first entered.

Series A5 investors entered at this stage

  • Mundi Ventures
  • Morro Ventures
  • AV8 Ventures
  • PayPal Ventures
  • Advent-Morro Equity Partners

Other known investors1 additional known investor

  • Overlook Ventures
Team profiled 4 named & role-tagged
Founders Hidden — book a demo/100 quality score
Key operators 2 quality Hidden — book a demo/100
Potential founders Hidden — book a demo likely future founders
Startup mafia Hidden — book a demo alumni-founded startups
Talent movements Hidden — book a demo in · Hidden — book a demo out past 12 months

Source: Dealroom Talent Intelligence.

Global footprint

Workforce and web traffic by country
Workforce by country
17 countries with
team presence
🇲🇽 Mexico18.8%
🇦🇷 Argentina14.8%
🇺🇸 United States11.9%
🇨🇴 Colombia10.9%
🇵🇪 Peru9.9%
Top 5 of 17 shown

Market sentiment

Posts on X, past 7 days

An AI-synthesised read of the highest-engagement posts about Ole Insurance Group on X, ranked by likes and reposts, corporate channels excluded.

Reading the room on X — pulling top posts and synthesizing themes…

Source: X recent search ranked by engagement (likes + retweets) · Synthesis by Claude · Cached for 1 hour

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