freelancer-benefits
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Wingspan
Wingspan is a New York-based payroll and management platform built specifically for the 1099 contractor workforce. It automates the full contractor lifecycle - onboarding, W-9 verification, background checks, same-day payments, tax withholding, and automated 1099 filing - and now ships that stack as an embeddable, white-label API (Wingspan Embed) for HR, HCM, and PEO platforms. The company has processed more than $3 billion in contractor payments and counts Teladoc Health and CRU Group among its customers.
Catch
Catch is a benefits platform built for the more than 50 million Americans who work for themselves and have no employer to hand them a health plan. It helps freelancers, contractors, gig workers and solopreneurs find, compare and enroll in health, dental and vision insurance, applying tax credits instantly so coverage costs less. The service is free to users. Founded in 2019 as a Y Combinator startup, Catch raised about $20M, was wound down by its original founders in early 2023, then bought and relaunched the same year by two operators who personally believed independent workers deserved a real safety net.