benefits-platform
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How a 1999 Perks Startup Became the Discount Engine Inside Half the Fortune 500
BenefitHub has spent 25 years quietly aggregating other people's deals into one company login. It says it has never had a down year - and most of the millions of people who use it have never heard the name.
Compt
Compt is a Boston-based HR software company that runs flexible employee stipends and Lifestyle Spending Accounts (LSAs) for employers. Instead of one-size-fits-all perks, employees choose how to spend an allowance across categories like wellness, professional development, childcare, home office and pet care; they submit a receipt and get reimbursed through payroll with the correct tax treatment applied automatically. Founded in 2018 by Amy Spurling, the reimbursement-based platform emphasizes IRS-compliant tax handling, high participation, and low administrative overhead, and operates across all 50 U.S. states and 75+ countries.
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.
Guy Benjamin
Guy Benjamin is the CEO and co-founder of Healthee, a New York-based company that uses AI to help employees understand and use their health benefits. A former Israeli Air Force fighter pilot with a Yale MBA and a McKinsey background, he started Healthee in 2021 after struggling to navigate his own employer benefits in the US. The company has grown past 15,000 customers, counts Instacart, SiriusXM, and Celonis among its clients, and has raised $111 million in total funding, including a $50 million Series B in 2025.
Justin Holland
Justin Holland is the co-founder and CEO of HealthJoy, a Chicago-based digital health company that turns the maze of employee benefits into a single AI-guided app. An MIT-trained engineer and serial entrepreneur with two prior exits (OpenInstall to AVG/Avast and FreeCause to Rakuten), he started HealthJoy in 2014 after a personal run-in with the American healthcare system left him unable to find out what his own care would cost. He has led the company for more than a decade, raised roughly $108M in venture financing through a Series D, and built a platform now used by hundreds of thousands of members to navigate care, cut costs, and reach a virtual assistant named JOY.
evermore
evermore (formerly Soda Health) is a healthcare technology company that administers Smart Benefits, connecting people to the products and services they need - healthy food, OTC medications, transportation and more - when they need them. Its Smart Benefits Operating System adjudicates purchases at the item level in real time across more than 70,000 retail locations, helping Medicare Advantage, Medicaid and commercial payers manage supplemental benefits, close care gaps and improve outcomes. The company rebranded from Soda Health to evermore in October 2025 after closing an oversubscribed $50M Series B led by General Catalyst.
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.
Anirban Gangopadhyay
Anirban Gangopadhyay is the co-founder and CTO of Angle Health, an AI-native health insurance platform serving small and mid-sized businesses across 44 U.S. states. A Columbia University computer scientist and former Palantir machine learning engineer, he previously served as a Stokes Scholar at the U.S. Department of Defense and co-founded Zircon Technologies - an AI-enabled clinical trial recruitment startup that was acquired - before building Angle Health through Y Combinator's W20 batch. Angle Health raised $134 million in a December 2025 Series B and has grown revenue 26x since its Series A, with a mission to redesign healthcare delivery through AI-first technology.