Enter, a São Paulo-based legal-AI startup founded in 2023, tripled its valuation to US$1.2 billion (R$5.9 billion) in a Series B round announced May 5 that raised over US$100 million led by Peter Thiel’s Founders Fund with participation from Sequoia Capital, Ribbit Capital, Atlantico, ONEVC, and Kaszek.
The deal makes Enter Latin America’s first AI unicorn and the first regional legal-AI company to cross US$1 billion. The company processes more than 300,000 lawsuits annually for clients including Nubank, Bradesco, Mercado Livre, Airbnb, Azul, and LATAM Airlines, with its EnterOS system covering everything from initial filings to settlement-cost calculations.
Key Points
— Series B raise: over US$100 million; valuation tripled to US$1.2 billion (R$5.9B).
— Lead: Founders Fund; participation by Sequoia, Ribbit, Atlantico, ONEVC, Kaszek.
— Latin America’s first AI unicorn; first regional legal-AI company over US$1B.
— EnterOS processes 300,000+ lawsuits per year; revenue up 10x since Series A.
— Brazil hosts ~75 million pending lawsuits and 90%+ of global labor cases.
The Deal Mechanics
The Rio Times, the Latin American financial news outlet, reports that the Series B was led by Founders Fund (Peter Thiel) with Sequoia Capital and Founders Fund having previously co-led Enter’s Series A round in 2025, while Ribbit Capital joined the new round alongside regional investors Atlantico, ONEVC, and Kaszek, marking continued institutional commitment from both Silicon Valley and Latin American venture capital. Founders Fund partner Matias Van Thienen said the bet is on Enter’s advantage in a highly litigious environment, telling Bloomberg the firm feels “very comfortable winning Brazil decisively”. Cofounder Mateus Costa-Ribeiro said Enter aims to become a “monopolistic force” in Latin American legal AI.
Enter was founded in 2023 by Henrique Vaz, Mateus Costa-Ribeiro, and Michael Mac-Vicar with the goal of building a global AI company from Brazil. Since its Series A round, revenue has grown more than 10x and the client base has tripled. The company plans to grow headcount from approximately 100 to 150 employees and expand into other markets that have not yet been disclosed.
How the Technology Works
EnterOS is an end-to-end litigation platform where AI agents handle every stage of a case before any human attorney is involved, from drafting initial petitions to calculating settlement costs and even researching weather conditions cited in airline-cancellation suits. The technology covers civil and labor cases and outputs are audited by partner law-firm attorneys for legal safety, while Enter charges roughly 30% of revenue on a success-fee basis tied to case outcomes with the rest invoiced upfront for technology usage. Cofounder Costa-Ribeiro said the harder integration challenge is connecting the AI to all legacy data sources required for case analysis.
Brazil’s Litigation Market Opportunity
The structural opportunity is unique: Brazil entered 2026 with approximately 75 million pending lawsuits, hosts more than 90% of the world’s labor-court cases, and runs as one of the most litigious jurisdictions globally. Enter’s 45+ enterprise clients now include heavily regulated banks (Nubank, Bradesco), e-commerce (Mercado Livre), and travel/airline companies (Airbnb, Azul, LATAM Airlines) that face high consumer-claim and labor-suit volume, with the company reporting billions of reais in client savings and higher case-success rates plus operational-cost reductions. CEPAL has framed Brazil’s litigation density as a structural inefficiency that AI tooling is positioned to attack.
| Element | Detail |
|---|---|
| Round announced | May 5, 2026 (Series B) |
| Amount raised | More than US$100M |
| New valuation | US$1.2B (R$5.9B); 3x prior |
| Lead investor | Founders Fund (Peter Thiel) |
| Co-investors | Sequoia, Ribbit, Atlantico, ONEVC, Kaszek |
| Founded | 2023, São Paulo |
| Founders | Henrique Vaz, Costa-Ribeiro, Mac-Vicar |
| Cases per year | 300,000+ via EnterOS |
| Headcount target | ~100 to 150 employees |
Connected Coverage
For broader Latin American technology and investment context, see our coverage of the Dominican Republic FDI surge in Q1 2026 and the Caribbean investment momentum and our analysis of the Lula-Trump White House meeting and Brazil’s evolving relationship with US capital markets.
What Happens Next
- Q2 2026: Enter targets growing headcount from 100 to 150 employees post-funding.
- H2 2026: Geographic expansion plans to be announced (markets not yet disclosed).
- Watch: Harvey (US$11B), Legora (US$5.5B), and Anthropic legal-AI moves as global benchmarks.
Frequently Asked Questions
What does Enter do?
Enter is a São Paulo-based legal-technology company that uses AI agents to handle end-to-end litigation in civil and labor cases, with the EnterOS platform drafting initial petitions, building legal defenses, calculating settlement costs, and even researching contextual data such as weather conditions cited in airline-cancellation lawsuits. Outputs are audited by partner attorneys for legal safety, and the company processes more than 300,000 lawsuits annually for over 45 enterprise clients. About 30% of revenue comes from case-success fees, with the rest billed upfront for technology usage.
Who invested in the Series B?
The Series B was led by Founders Fund (Peter Thiel) with participation from Sequoia Capital, Ribbit Capital, Atlantico, ONEVC, and Kaszek, and Sequoia and Founders Fund had also co-led Enter’s Series A in 2025, signaling continued institutional commitment. The round raised over US$100 million and tripled Enter’s valuation to US$1.2 billion (R$5.9 billion). Founders Fund partner Matias Van Thienen called the investment a bet on Enter’s edge in one of the most litigious environments in the world.
How does Enter compare to global peers?
Enter is part of a global wave of legal-AI startups attracting major capital, with US-based Harvey recently valued at US$11 billion and Sweden’s Legora at US$5.5 billion in recent rounds. While Enter’s US$1.2 billion valuation is smaller in absolute terms, it makes Enter the first AI unicorn in Latin America and the regional leader in legal AI. Cofounder Mateus Costa-Ribeiro told Bloomberg the company aims to become a “monopolistic force” in Latin American legal AI before broader international expansion.
Why is Brazil a strategic market?
Brazil entered 2026 with approximately 75 million pending lawsuits and accounts for more than 90% of the world’s labor-court cases, making it one of the most litigious jurisdictions globally. The volume creates a structural opportunity for AI tools that can automate consumer claims, labor disputes, and litigation workflows for enterprises facing high case loads. Enter’s 45+ clients include Nubank, Bradesco, Mercado Livre, Airbnb, Azul, and LATAM Airlines, all heavy consumers of litigation services in Brazil.
Updated: 2026-05-07T15:30:00Z by Rio Times Editorial Desk