A pharmacy benefits challenger found a bigger problem hiding in the paperwork. Judi Health is putting medical and pharmacy claims on the same system - and selling the machinery to other benefit administrators.
A flat fee. A visible drug price. Then a software platform built to make both work. Capital Rx, now Judi Rx, is taking its pharmacy experiment into the rest of health benefits.
Castlight supplies the map. Vera supplies the medicine. Together, apree health is testing whether better directions and a real primary care relationship can make employer healthcare work.
Employers get a ceiling on health-benefit costs. Workers get a market full of choices - and a licensed human to call. Remodel Health raised more than $100 million on the belief that this awkward trade can become mainstream infrastructure.
The Toronto company started by helping workers book massages. A decade and more than $285 million in venture funding later, it is selling the rails - and now the AI agents - behind healthcare's digital front door.
Tenure Health started with a consumer problem - retirement healthcare feels like paperwork with a pulse. Three years, roughly $7 million and several stops and starts later, NCD bought the company for the product machinery behind the promise.
Mercer built an 80-year business around decisions companies cannot afford to guess at - what to pay, which benefits to fund, how to redesign work and where to invest retirement money. Now its vast store of workforce data is becoming a product in its own right.
Sun Life spent 160 years learning how to price the future. Now it is turning that patience into a three-part business spanning protection, workplace health and global asset management.
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.
Binkey is a Washington, DC fintech that lets online merchants accept pre-tax health benefit dollars - FSA, HSA, and related accounts - as payment at checkout. Its AI-powered engine classifies products at the SKU level to determine IRS eligibility in real time, automates claim filing and reimbursement, and routes funds through developer-friendly APIs. Products span Binkey Pay (checkout acceptance), FSA + HSA Rewind (recovering unused benefit dollars from past purchases), and Binkey Vision (out-of-network vision reimbursement). The company raised $3.3M in seed funding in 2023.

River Health is a Minneapolis digital health company building the first health plan designed specifically for hourly and mixed workforces - the roughly 75 million American workers who earn too much for Medicaid but can't afford traditional insurance. For a flat monthly fee with no copays, deductibles, or hidden charges, members get virtual and in-person primary care, behavioral health, labs, and prescriptions delivered to their door. River sells directly to employers like Taco Bell and Raising Cane's who want to offer real benefits to workers the insurance industry has long ignored.
Collective Health is a San Francisco-based health benefits technology company that operates an integrated platform for self-funded employers. It brings medical, dental, vision, pharmacy, and digital health partners together in one system, pairing claims administration with a member app, care navigation, and analytics so employers can control costs while making coverage easier for employees to understand, navigate, and pay for.
Surest is a UnitedHealthcare employer-sponsored health plan that strips out deductibles and coinsurance and instead shows members clear, upfront prices for care before they book it. Founded in 2016 as Bind in Minneapolis, the plan lets people compare providers and treatment options by cost and quality through an app, then pay a single known copay. Rebranded from Bind to Surest in 2022 after UnitedHealthcare took majority ownership, it has grown into the fastest-growing plan in UnitedHealthcare's book, serving close to one million members across employers from family businesses to the Fortune 100.
Thatch is a San Francisco health benefits platform that lets employers give workers a tax-free monthly healthcare budget instead of a one-size-fits-all group plan. Employees shop a marketplace for their own medical, dental and vision coverage, then spend any leftover budget on care through a Thatch debit card. Built around ICHRA - a 2020-era IRS rule - the company aims to unbundle health insurance from a single employer plan and hand the choice back to individuals. Since launching in 2023 it has served more than 1,000 businesses and raised about $84.5 million across seed, Series A and Series B rounds.
Zorro is an AI-powered ICHRA platform that swaps rigid group health plans for a defined-contribution model - think 401(k), but for health insurance. Employers set a budget, employees get a personal allowance, and Zorro's decision-support engine helps each person pick an individual plan that actually fits their doctors, medications, and wallet. The platform serves employers, employees, and the brokers who sell to them, and clients have averaged over 20% premium savings versus traditional group coverage.
Transcarent is a consumer-directed health and care platform built for self-insured employers and their employees. Founded in 2020 by Livongo creator Glen Tullman with General Catalyst's Hemant Taneja, it bundles 24/7 doctors, pharmacy, surgery, cancer and behavioral care into one app powered by its AI experience WayFinding. After its $621M merger with Accolade in 2025, the company now covers roughly 20 million Americans.