Ensurem
Medicare insurance comparison and enrollment platform serving consumers aged 65+ across all 50 states
Overview
Ensurem is a Medicare insurance distribution platform operating under HealthPlanOne, LLC, a licensed health insurance intermediary headquartered in Shelton, Connecticut. The company connects Medicare-eligible consumers -- primarily individuals aged 65+ and those under 65 with qualifying disabilities -- with Medicare insurance options from over 36 insurance organizations offering more than 4,135 products.
The platform operates a multi-channel strategy combining online self-service tools, licensed insurance agent support, and digital marketing. Ensurem is licensed in all 50 states and Washington D.C., and also operates under the ClearMatch Insurance Agency brand in California, Florida, and New York. The company runs 24+ branded consumer websites and has grown to a team of 350+ employees, earning recognition as one of the fastest-growing companies in Florida.
Founded in 2016 by Dave Rich and operating under parent company HealthPlanOne (established 2006), Ensurem was acquired by Miami-based private investment firm 777 Partners in May 2025, continuing its growth as a significant player in the Medicare marketplace.
Products & Services
Medicare Advantage Plan Comparison and Enrollment
Online comparison and enrollment platform for HMO, PPO, and PFFS Medicare Advantage plans from 36+ insurance carriers. Consumers can compare benefits, costs, and coverage across 4,135+ available products and enroll online or with agent assistance.
Key Features
- Side-by-side plan comparisons across all major Medicare Advantage carriers
- Online enrollment with real-time eligibility verification
- Licensed agent support via phone and online chat
Target Users: Medicare-eligible consumers aged 65+ and qualifying individuals under 65
Medicare Supplement (Medigap) Plans
Comparison and enrollment services for Medicare Supplement insurance plans, covering costs not included in Original Medicare such as deductibles, copayments, and coinsurance.
Key Features
- Plan comparisons across multiple Medigap carriers
- Guidance from licensed agents on coverage options
- Multi-state availability (all 50 states + D.C.)
Target Users: Medicare beneficiaries seeking gap coverage
Prescription Drug Plans (PDP)
Standalone Medicare Part D prescription drug plan comparison and enrollment, including formulary information and cost analysis.
Key Features
- Formulary lookup and drug cost comparisons
- Medicare Part D plan enrollment
- Integrated with overall Medicare plan shopping experience
Target Users: Medicare beneficiaries seeking prescription drug coverage
Licensed Agent Enrollment Services
A network of licensed insurance agents providing personalized consultation and enrollment assistance for consumers who prefer guided support over self-service.
Key Features
- Phone and online chat with licensed agents
- Plan-switching and renewal assistance during Medicare Open Enrollment
- Available across all 50 states and D.C.
Target Users: Medicare-eligible consumers preferring assisted enrollment
At a Glance
- Founded
- 2016
- Headquarters
- Shelton, Connecticut
- Employees
- 201-500
- Funding
- Acquired
Category & Focus
- Category
- Distribution & Sales
- Subcategories
- Medicare marketplace insurance comparison digital enrollment consumer-facing distribution
- Insurance Verticals
- Health
- Target Customers
- Consumers
Customers
- Aetna
- Anthem
- Humana
- United Healthcare
- Wellcare
- HealthSpring
Links
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Last updated: 2026-04-10