benefits-enrollment
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Pasito
Pasito is a New York-based AI company building an AI-native workspace for group health, life, and retirement benefits. Founded in 2021 by Pauline Roteta, Ignacio Ampuero, and Julie Scotland, and backed by Y Combinator, the platform ingests unstructured plan documents and employee census data into a unified data layer, then deploys engagement AI agents to automate benefits work across sales, quoting, marketing, enrollment, support, and claims. Pasito serves carriers, brokerages, and consultants including New York Life, Reliance Matrix, OneDigital, and Daybright Financial. In February 2026 it raised a $21 million Series A led by Insight Partners.
Workers Benefit Fund
Workers Benefit Fund is a New York-based, mission-driven company that closes the benefits gap for gig workers, freelancers and independent contractors. Acting as a PEO-style solution for the gig industry, it builds the technology, outreach infrastructure and partnerships that platforms, labor unions and public institutions need to connect non-traditional workers with health, wellness and financial benefits. Its flagship work powers the Drivers Benefits program alongside The Black Car Fund, which has enrolled tens of thousands of New York for-hire drivers at no cost to them.
Ounce of Care
Ounce of Care (brand name: Ounce) is a New York-based company building the tech-enabled resident services layer for affordable housing. It embeds on-site Community Navigators and virtual care teams inside apartment communities, then uses its Ounce Hub platform to enroll residents in public benefits like SNAP and Medicaid, coordinate health and social services, and run educational programming. The result is a rare win-win: residents get stability and support, and property owners get better retention, occupancy, and asset performance.