Ole Insurance Group
Olé Life is a digital-first life insurance carrier serving Latin American and Caribbean families across 38 countries with USD-denominated term life coverage from $100K to $10M, distributed via 100% online enrollment and 4,000+ advisors.
- Company typePrivate
- Founded2022
- HeadquartersSan Juan, Puerto Rico
- Headcount11–50
- GTM typeB2C
- OfferingServices
What Ole Insurance Group does
Ole Insurance Group, operating commercially as Olé Life, is a digital life insurance carrier targeting families across 38 countries in Latin America and the Caribbean. Founded in 2021 with corporate headquarters in Miami and a regulated Class 5 international insurer entity in San Juan, Puerto Rico, the company addresses a regional gap in USD-denominated life insurance, where local products are typically denominated in volatile currencies and rely on exam-intensive underwriting. Olé Life distributes coverage through a hybrid model combining direct-to-consumer digital enrollment with a network of more than 4,000 insurance advisors. The product portfolio is anchored by Easy Term (USD $100K to $1M coverage, no medical exams required) and Master Term (USD $1.1M to $10M coverage, tele-underwriting via video conference), with optional living benefit riders covering return of premium, critical illness and cancer, accidental death/disability, and income replacement. Both products are underwritten by Olé AI, a proprietary automated evaluation system that processes applicant data to enable enrollment in under 10 minutes, supported by member and advisor mobile apps, an advisor web portal, and the OléLifeGo training platform. The business operates on a recurring monthly subscription premium model with fixed pricing throughout the policy term. Risk-bearing capacity is provided through a 90% quota-share reinsurance arrangement with Munich Re (joined by Partner Re and RGA from October 2023 and Swiss Re from April 2025), and the company carries an AM Best Financial Strength Rating of B++ (Good) achieved within 20 months of launch. Olé Life has raised approximately USD $25 million across funding rounds, including a $13 million Series B led by PayPal Ventures in January 2025, and operates with 11-50 employees.
Ole Insurance Group firmographics
Firmographics- Name
- Ole Insurance Group
- Legal name
- Olé Insurance Group Corp. I.I.
- Website
- https://olelife.com
- Company type
- Private
- Founded year
- 2022
- Operating status
- Operating
- Headcount range
- 11–50 employees
- Short description
- Olé Life is a digital-first life insurance carrier serving Latin American and Caribbean families across 38 countries with USD-denominated term life coverage from $100K to $10M, distributed via 100% online enrollment and 4,000+ advisors.
- Ownership category
- akta.pro rank
Ole Insurance Group industry classification
Industry- Product category
- Digital Life Insurance
- NAICS
- Direct Life Insurance Carriers (524113), Direct Health and Medical Insurance Carriers (524114), Insurance Agencies and Brokerages (524210)
- SIC
- Life Insurance (6311), Accident & Health Insurance (6321), Insurance Agents, Brokers & Service (6411)
- akta.pro primary industry
- Guaranteed Issue Term Life Insurance (FSAIAAAG)
- akta.pro secondary industries
- Accidental Death Only (AD-Only) Insurance (FSAIALAI), Ancillary & Supplemental Health Products (Accident/Critical Illness/Hospital Indemnity) (HLAEABAJ)
Keywords
Where Ole Insurance Group is headquartered
LocationHeadquarters
- HQ city
- San Juan
- HQ country
- Puerto Rico
- HQ region
- Latin America
Offices2 records
Markets served
Ole Insurance Group business model
Business model- GTM type
- B2C
- Offering type
- Services
- Cost components
- Personnel, Technology or R&D, Operations, Marketing or Sales, Infrastructure, Supply Chain
Revenue model
- Life Insurance Premiums: Recurring premium payments for term life insurance policies (Easy Term and Master Term) with fixed premiums throughout the contracted term. USD-denominated coverage with pricing that remains stable without annual increases.
- Living Benefits Add-ons: Optional rider benefits including return of premium, accidental death/disability coverage, income protection, and critical illness/cancer protection sold as add-ons to base policies.
Pricing tiers
| Model | Billing | Price |
|---|---|---|
| Subscription | Monthly | Easy Term - Entry-level term life insurance coverage |
| Subscription | Monthly | Master Term - High-value term life insurance coverage |
Go-to-market motion3 records
Distribution channels3 records
Marketing channels5 records
Ole Insurance Group product offering
Product offeringCore offering
Ole Insurance Group sells USD-denominated term life insurance products to individuals and families across Latin America and the Caribbean. The company offers two core products: Easy Term (coverage from $100,000 to $1,000,000 with no medical exams required) and Master Term (coverage from $1,100,000 to $10,000,000 with AI-powered underwriting), both distributed through a 100% digital enrollment process powered by Ole AI. Optional living benefits add-ons include return of premium, critical illness/cancer protection, accidental death/disability, income replacement, and terminal illness cash advance.
Product overview
Olé Life is a digital life insurance platform offering a portfolio of USD-denominated term life insurance products. The core offerings are Easy Term (up to $1,000,000 coverage) and Master Term (up to $10,000,000 coverage), both underwritten through a simplified digital process powered by Olé AI. Living benefits including Return of Premium, Critical Illness/Cancer Protection, Accidental Disability, Income Replacement, and Funeral Expenses are available as add-on modules bundled with base policies. The company supports distribution through multiple digital channels including the Member App for customers, Advisor App and Advisor Portal for agents, and OlelifeGo for training and materials. Coverage is available across 38+ countries in Latin America and the Caribbean.
Differentiator
Problem solved
Functional benefit
Brands
- Easy Term: Term life insurance coverage from USD $100,000 to $1,000,000 with simplified evaluation, no medical exams required, and automatic approval.
- Master Term
- Olé Life Go
Products and services
- Easy Term Term life insurance providing financial protection from USD $100,000 to $1,000,000 with simplified evaluation supported by Ole AI, no medical exams required, and enrollment completed in under 10 minutes for individual consumers and families across Latin America and the Caribbean.
- Master Term High-coverage term life insurance for USD $1,100,000 to $10,000,000 featuring dynamic application process with AI and predictive algorithms, faster underwriting via tele-underwriting video conferences, and competitive rates up to 30% below competitors for high-net-worth individuals and families seeking comprehensive financial protection.
Quantifiable outcome
- Enrollment completed in under 10 minutes
- +5 more outcomes
Companies that use Ole Insurance Group
Customer profileNamed customers6 records
Segments4 records
Ideal customer profiles3 records
Ole Insurance Group technology and API
TechnologyTechnology focussed Yes
API detail
- Has API
- No
- API docs
- API detail
Core technology
AI maturity
App detail
Integration6 records
AI capability5 records
Feature4 records
Ole Insurance Group partnerships and signals
Strategic signalPartnerships
Four partnerships are on record, tiered core.
- Swiss RecoreSwiss Re, one of the world's leading reinsurance providers, joined Olé Life as a strategic reinsurer as of April 1, 2025. This partnership strengthens the company's financial foundation and reinforces its long-term commitment to protecting families across Latin America.
- Munich RecoreMunich Re, the world's largest reinsurer, became a commercial partner in a 90% reinsurance arrangement with risk-sharing contract. This guarantees continuity of the same reinsurer throughout the full policy term, providing certainty to policyholders.
- Partner RecorePartner Re is part of the reinsurance family alongside Munich Re and RGA, strengthening Olé's commitment, support, and seriousness in the business.
- RGAcoreRGA is part of the reinsurance family alongside Munich Re and Partner Re, providing risk-sharing reinsurance support.
Scale indicators6 records
Recent moves6 records
Expansion highlights6 records
Ole Insurance Group competitors and assessment
Company assessmentDirect peers
- Ethos Life: Ethos is a digital life insurance carrier offering simplified-issue term and whole life policies with AI-driven underwriting and no-medical-exam coverage up to multi-million dollar limits — directly comparable to Olé's Easy Term and Master Term products.
- Haven Life: Haven Life (a MassMutual subsidiary) pioneered digital term life with streamlined online underwriting and no-exam options — a near-exact analogue of Olé's product strategy, although focused on the US market.
- Ladder Life: Ladder is a digital term life insurer that allows coverage adjustments online without medical exams, targeting a similar simplified-issue digital experience and competitive pricing model as Olé.
- Bestow: Bestow offers fully digital term life insurance with instant decisions and no medical exams for coverage typically up to $1M — directly comparable to Olé's Easy Term positioning and underwriting approach.
- Pan-American Life Insurance Group: Pan-American Life is a major LATAM-focused life and health insurer where Olé's founder previously led the international medical division; it is one of the closest direct competitors in the USD-denominated, cross-border LATAM insurance market.
- Breeze: Breeze is a digital life insurance platform offering no-exam term life online with instant approvals — closely aligned with Olé's simplified digital underwriting and direct-to-consumer experience.
Broad incumbents
- Lemonade: Lemonade is an AI-native digital insurer expanding from renters and auto into life insurance across multiple geographies; it represents the broader incumbent digital-insurance category against which Olé's tech stack and AI positioning compete.
- Mapfre: Mapfre is one of the largest insurance groups in the Spanish-speaking world, with deep LATAM distribution and product breadth far beyond Olé — a broad incumbent against which Olé's digital-only model competes for advisor mind-share.
- MetLife: MetLife is a global life insurance incumbent with significant LATAM operations offering a broad range of life, accident, and health products — a large legacy competitor Olé must differentiate against on digital UX and simplified underwriting.
- Prudential Financial: Prudential is a global life insurance leader with growing digital distribution and LATAM presence through Prudential of Brazil and other units — a broad incumbent that competes for the same pool of life insurance buyers Olé targets.
Market position
Strengths1 record
Weaknesses1 record
Competitive moat6 records
Key risks6 records
Key highlights7 records
Customer concentration
Ole Insurance Group social profiles
Digital presenceOle Insurance Group compliance and trust
Trust signalCompliance2 records
Ole Insurance Group financial estimates
Financial estimateRevenue estimate
Valuation estimate
Ole Insurance Group leadership team
Management profileNumber of profiles
Profiles1 record
Ole Insurance Group funding detail
Funding detailFunding overview
Funding rounds3 records
Investors5 records
Funding detail is available on the Subscription and Enterprise plan.Contact sales →
Ole Insurance Group M&A and investment
M&A and investmentM&A
Investments
M&A and investment is available on the Subscription and Enterprise plan.Contact sales →
Frequently asked questions about Ole Insurance Group
What does Ole Insurance Group do?
Ole Insurance Group sells USD-denominated term life insurance products to individuals and families across Latin America and the Caribbean. The company offers two core products: Easy Term (coverage from $100,000 to $1,000,000 with no medical exams required) and Master Term (coverage from $1,100,000 to $10,000,000 with AI-powered underwriting), both distributed through a 100% digital enrollment process powered by Ole AI. Optional living benefits add-ons include return of premium, critical illness/cancer protection, accidental death/disability, income replacement, and terminal illness cash advance.
Is Ole Insurance Group a public or private company?
Ole Insurance Group is a private company. It is classified as venture growth investor backed and is currently operating.
When was Ole Insurance Group founded?
Ole Insurance Group was founded in 2022. It employs 11 to 50 people.
Where is Ole Insurance Group based?
Ole Insurance Group is headquartered in San Juan, Puerto Rico, in the Latin America region.
How does Ole Insurance Group make money?
Two revenue lines are on record. Life Insurance Premiums are the primary driver. The others are living Benefits Add-ons.
Who are Ole Insurance Group's main competitors?
Direct peers on record are Ethos Life, Haven Life, Ladder Life, Bestow, Pan-American Life Insurance Group and Breeze. Broad incumbents are Lemonade, Mapfre, MetLife and Prudential Financial.
Does Ole Insurance Group have an API?
No public API is recorded for Ole Insurance Group.
What industry is Ole Insurance Group in?
Ole Insurance Group's product category is Digital Life Insurance. Its primary akta.pro industry code is FSAIAAAG, Guaranteed Issue Term Life Insurance, with a secondary code of FSAIALAI, Accidental Death Only (AD-Only) Insurance. Its NAICS code is 524113 and its SIC code is 6311.