Connie Health Raises $40M Series B, Buys Clearlink Medicare

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Connie Health, a Medicare platform based in Boston, Massachusetts, has raised $40 million in a Series B round and used the moment to announce a major acquisition. The financing, announced on June 18, 2026, was led by HealthQuest Capital with participation from JSL Capital, alongside existing investors Khosla Ventures, aMoon, and Pitango HealthTech. The round brings the company’s total funding to $85 million.

Alongside the raise, Connie Health completed the acquisition and integration of Clearlink’s Medicare business. That deal marks the company’s 10th completed acquisition, a pace that points to a deliberate strategy of growing by absorbing established books of business and folding them into its own operation.

The company runs an AI-enabled Medicare platform built to help seniors navigate their healthcare options. It pairs proprietary technology with a network of local, trusted agents who help seniors find and enroll in the right coverage. That combination of software and human guidance is central to the pitch, since choosing a Medicare plan is a notoriously confusing process for many older adults.

What makes the acquisition strategy work, according to the company, is its technology platform, which it uses to integrate and scale large books of insurance business after each deal. Rather than treating acquisitions as one-off purchases, Connie Health folds them into a single system.

With $40 million in new capital and its 10th acquisition complete, the Boston company is positioning itself to keep expanding its share of the Medicare market while leaning on technology to tie its growing operation together.