Roger Cawdette
| Roger Cawdette | |
| Occupation | Entrepreneur, CEO |
|---|---|
| Known for | Co-founder and CEO of Village Labs |
Roger Cawdette is an American entrepreneur and the co-founder and CEO of Village Labs, a financial technology and human resources company that helps American businesses transition to employee ownership through employee stock ownership plans (ESOPs). Village Labs was part of Y Combinator's Summer 2024 batch and is based in New York City.[1]
Early life and education
Cawdette attended Boston Latin School in Boston, Massachusetts, where he played soccer.[2] He subsequently enrolled at Harvard University, where he studied technology and social innovation. He left Harvard after his sophomore year to pursue entrepreneurship full-time.[3]
Career
Finary
In 2020, Cawdette co-founded Finary, a social investing platform aimed at Generation Z and millennial investors. The idea originated from observing his Harvard classmates using informal group chats on platforms like Discord and GroupMe to share investing information. Finary was described as "Discord for investing" and sought to make stock market participation more accessible to younger demographics. The company was backed by Y Combinator (Winter 2021 batch), Upfront Ventures, and Dash Fund. In April 2021, Finary raised $3.2 million in funding.[4]
Village Labs
In 2023, Cawdette co-founded Village Labs. The company develops AI software for ESOP administration and advisory firms, with the goal of making it easier for businesses to become and remain employee-owned. Village Labs offers several products, including Peninsula, an AI platform for ESOP advisory firms that enables the building and deployment of AI agents for complex workflows, and a repurchase forecasting tool with advanced modeling and scenario analysis capabilities.[5]
The company addresses what has been described as a "Silver Tsunami" — an anticipated wave of retirements among approximately 2.9 million Baby Boomer business owners in the United States. Village Labs positions ESOPs as an alternative to traditional acquisition by firms such as private equity buyers, allowing retiring owners to sell to their employees while providing tax benefits and preserving jobs. Existing ESOPs in the United States, including those at companies such as Bob's Red Mill, Harpoon Brewery, and Recology, benefit over 14 million workers and have created an estimated $2.1 trillion in employee wealth.[1]
The company maintains SOC 2 Type II compliance and employs AES-256 encryption with a zero-retention data policy.
References
- ↑ 1.0 1.1 "Village Labs – Y Combinator". 'Y Combinator}'. Retrieved 2026-03-18.
- ↑ "Roger Cawdette's High School Career Home". 'MaxPreps}'. Retrieved 2026-03-18.
- ↑ "Finary's Roger Cawdette on Market Pops Becoming Pop Culture". 'NYC Founder Guide}'. Retrieved 2026-03-18.
- ↑ "Finary Raises $3.2M To Build The Gen-Z Group Chat Investing Platform". 'Forbes}'. Retrieved 2026-03-18.
- ↑ "Village Labs – AI Software for ESOPs & Advisory Firms". 'Village Labs}'. Retrieved 2026-03-18.