For 70 years Aflac has sold Americans the thing their health plan skips: cash in hand when an accident or illness stacks up the bills insurance won't touch.
Horace Mann built an 80-year business by studying one customer more closely than most insurers study a market. Its wager is that understanding the financial life of a teacher - from the school parking lot to retirement - can still be a durable advantage.
The 155-year-old professional services firm has turned uncertainty into a $27 billion business. Its real product is neither a policy nor a spreadsheet, but a better-informed decision before the bill comes due.
The Hartford has spent 216 years learning how America breaks, rebuilds and gets back to work. Its next act is narrower, more digital and still built around an old-fashioned promise: price risk before trouble arrives, then show up when it does.
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.
The 158-year-old insurer is becoming a three-engine financial platform: workplace benefits, retirement-risk transfer and global asset management - all hidden behind one familiar blue-and-green M.
The Tampa firm grew from a Florida brokerage into a $1.5 billion national platform. Its next act is less about selling policies than connecting advice, underwriting, embedded distribution and AI into one insurance operating system.
Equitable has spent 167 years selling certainty. Now it is redesigning itself around advice, assets and a proposed merger that would put $1.5 trillion under one roof.
Insperity built a $6.8 billion business by taking on the work small companies cannot afford to get wrong. Now its service-heavy PEO model is being rebuilt for a Workday world.
Principal began by selling affordable life insurance to bankers in 1879. Today, its quiet advantage is a workplace-to-wealth pipeline that reaches millions of people before they ever choose a financial brand for themselves.
CBIZ spent three decades stitching local specialists into a national middle-market machine. After swallowing Marcum, it is now set to become part of Grant Thornton - a $5 billion coda to the accounting industry's consolidation race.
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.

After three tours as a CFO, Amy Spurling stopped treating employee perks as a shopping list. Compt is her attempt to turn a stubborn budget line into a system built on choice, evidence, and trust.
Reduce HR admin time, run payroll in minutes, streamline all your payments, and deliver world-class employee experiences - unified on one platform hyperlocalised for the GCC.
Abhi is a MENAP embedded-finance company that started by letting salaried workers draw wages they have already earned before payday, and has grown into a full stack of employer-facing tools - earned wage access, payroll processing, payroll financing and invoice factoring - plus its own microfinance bank in Pakistan. Founded in 2021 by Omair Ansari and Ali Ladhubhai and backed by Y Combinator (S21), it now serves over a million people across thousands of companies in Pakistan, the UAE, Saudi Arabia and Oman, and was the first MENAP fintech named a World Economic Forum Technology Pioneer.
Eden Care Medical is a licensed digital health insurer building the claims and distribution infrastructure that modernizes health insurance in Africa. Starting in Rwanda and expanding into Kenya, it sells group health cover to employers and their staff, then runs the whole value chain - HR admin portal, an employee app for navigating care and wellness, and digital tools for hospitals and clinics - to cut the cost of insurance in a market where operating costs run 2.2x the global average and penetration sits near 0.2%.
FinFlx is a Dubai-based fintech that helps UAE companies forecast, fund and manage their employees' end-of-service gratuity in line with local labour law. Its platform automates gratuity calculations for HR and finance teams, lets employers park those liabilities in a segregated, professionally managed fund, and gives employees an app with a flexible savings account paying a guaranteed 4-5% return. Founded by Amr Yussif and Matthieu Capelle after Yussif's own gratuity was withheld, FinFlx went through Y Combinator's W22 batch and is regulated by the FSRA in Abu Dhabi Global Market.
GIMO is a Vietnamese fintech that lets blue-collar workers draw a portion of their already-earned wages before payday through a mobile app connected to their employer's payroll. Founded in 2019 and part of Y Combinator's Winter 2022 batch, GIMO works with manufacturers and other large employers to give underbanked staff an alternative to predatory informal lenders, and has grown to serve hundreds of thousands of workers across the country.
Doctor Anywhere is a Singapore-headquartered, tech-led healthcare company founded in 2017 by Lim Wai Mun. It started as a telemedicine app that put a licensed doctor on a video call within minutes, then deliberately grew downward into the physical world - GP clinics, specialist practices, health screening and imaging suites, home visits, medication delivery and an in-app health marketplace. The company describes the result as a 'Hospital Anywhere' model: one app that carries a patient from a 2am sore throat to a knee surgeon, across Singapore, Malaysia, Thailand, Indonesia and the Philippines. It serves roughly 3 million users, sells to consumers, corporates and insurers, and has raised about US$176 million from investors including Asia Partners, Novo Holdings, Square Peg, EDBI, IHH Healthcare, Philips and Pavilion Capital.
Mekari is Indonesia's leading business software company, offering a unified SaaS ecosystem that helps companies run HR, payroll, accounting, CRM, expenses, and digital signing on a single connected platform. Formed in 2019 from the merger of Sleekr, Talenta, Jurnal, and Klikpajak, Mekari now serves roughly 300,000 businesses and more than a million users across the country, positioning itself as the operating backbone for Indonesian SMBs and enterprises going digital.
PolicyStreet is a Malaysia-based, full-stack insurtech group that makes insurance simpler and more accessible across Southeast Asia and Australia. Founded in 2016 and operating under holding company Polisea, it works with more than 40 life, general and Takaful providers to deliver embedded insurance, employee benefits, gig-worker protection, financial advisory and an online insurance marketplace through B2B, B2B2C and direct-to-consumer channels. Backed by Khazanah Nasional, Cool Japan Fund and others, it has grown to serve over 10 million customers and turned profitable in 2025.
Basic Capital is a New York fintech building a modernized 401(k) and IRA platform that lets everyday workers finance their retirement investments rather than only contribute out of pocket. For every dollar a saver puts in, the company supplies supplemental capital - roughly four additional dollars - so contributions are deployed into diversified portfolios of ETFs, bonds, and access to alternatives like private credit. Founded by former Goldman Sachs banker Abdul Al-Asaad, it positions itself as the first platform to bring financing and alternative assets into tax-advantaged retirement accounts, and raised a $25M Series A in August 2025 led by Forerunner and Lux Capital.
Bento is a Boston-based dental benefits technology company that replaces traditional dental insurance with a transparent, self-funded model. Its patented, AI-powered platform connects employers, associations, dentists and DSOs with real-time claims adjudication, customizable plan design and in-office membership plans. The only dental benefits solution endorsed by the American Dental Association, Bento says it can cut employer dental costs by 20-40% while giving members access to hundreds of thousands of provider access points nationwide.
Cariloop is a Dallas-area health and wellness company that helps working caregivers manage the demands of caring for children, aging parents, and other loved ones. Sold to employers as a benefit, its Caregiver Support Platform pairs each family with a dedicated, licensed Care Coach and a secure portal for storing documents, finding and booking care providers, and navigating medical, financial, and legal questions. Founded in 2012 by Michael Walsh and Steven Theesfeld, the company has supported more than 300,000 families and raised roughly $43 million across seed through Series C rounds.
Carrot Fertility is a global fertility and family-building benefits platform that employers and health plans offer to their people. It covers the full journey - fertility preservation, IVF and IUI, pregnancy, adoption, surrogacy, low-testosterone care and menopause - with an expert Care Team, a global provider network, and the Carrot Card payment platform. Founded in 2016 after co-founder Tammy Sun faced a five-figure out-of-pocket egg-freezing bill, Carrot serves members in more than 195 countries and positions itself as a data-driven, outcomes-focused alternative to leaving fertility care to employees to navigate alone.
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.
Healthcare Highways is a Frisco, Texas-based health plan and provider network company that builds and operates curated, high-performance medical provider networks. Founded in 2010, it helps self-funded and level-funded employers, health systems, brokers, and third-party administrators lower healthcare costs and improve access by aligning the interests of providers, employers, and members - offering an alternative to the large national insurance carriers.
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.
LifeCare is a Shelton, Connecticut-based provider of employer-sponsored work-life benefits, best known for its Backup Care Connection service and the LifeMart employee-discount marketplace. Founded in 1984, the company helps large employers and federal agencies support their workforce with last-minute child, adult, senior and pet care, along with senior-care management, tutoring, and everyday savings. LifeCare has served tens of thousands of client organizations covering roughly 100 million members and, since October 2020, has operated as part of Care.com (an IAC company) under the CareBenefits umbrella.
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.