open-enrollment
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Jellyvision turned a game-show trick into a benefits business
The makers of You Don’t Know Jack found a second act in the least festive corner of working life: employee benefits. ALEX turns a bewildering choice into a conversation - and is now moving into enrollment itself.
Bennie wants your benefits to work after open enrollment
Buying health insurance is only the opening act. Bennie pairs a full-service brokerage with an app and human advocates to handle the awkward business of actually using it.
PlanSource Wants to Make Benefits Admin Boring - and That’s the Point
HR teams do not need another dazzling demo. They need the newborn to be covered, the carrier file to match and open enrollment to end without a fire drill. PlanSource has spent nearly two decades turning that unglamorous promise into enterprise software.
Healthee
Healthee is an AI-powered health benefits platform that helps employees understand, navigate, and use their health insurance. Its virtual assistant, Zoe, answers plan-specific questions about coverage, providers, and costs in plain language across 50+ languages, while giving HR teams and brokers tools to cut administrative burden and healthcare spend. Founded in 2021 and headquartered in New York with R&D in Tel Aviv, Healthee serves 15,000+ customer organizations including Instacart, SiriusXM, and Celonis, and raised a $50M Series B in 2025.
HealthSherpa
HealthSherpa is the largest private enrollment platform for Affordable Care Act (ACA) health insurance in the United States. Born in 2013 as a faster, cleaner alternative to a glitchy HealthCare.gov, it now helps millions of Americans shop, compare, and enroll in subsidized marketplace plans in about seven minutes, while giving tens of thousands of agents and brokers free tools to manage their books of business. The company runs a federally approved Enhanced Direct Enrollment (EDE) platform used by consumers, insurance carriers, and agencies alike.
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.