Can A Birth Control Startup Become The Future Of Medicaid-Friendly Digital Health?

For too long, women’s and reproductive healthcare has been underfunded, overlooked, and underserved. But a new wave of mission-driven companies is rewriting that script. At the forefront is Twentyeight Health, the Gen Z renegade that launched in 2018 and quickly made its mark by delivering inclusive, affordable access to birth control and sexual health services. With a focus providing on providing frictionless access, the platform has earned trust where others have ignored need.

Now, Twentyeight is expanding its services and moving beyond contraception into areas like prenatal care, STI testing, and mental health referrals. In doing so, it is laying the foundation for a full-spectrum, financially accessible digital health platform tailored to those most often left out.

Closing the Coverage Gap

Founded in 2018, Twentyeight Health now operates in over 30 states, delivering reproductive healthcare to communities often left behind by traditional systems. The company’s Chief Operating Officer, Mara Castro, describes the company’s founding insight this way: “We saw a huge opportunity to bring dignity and discretion to reproductive care for individuals who are often left out of innovation.”

The need is substantial. More than 70 million Americans are enrolled in Medicaid, and data consistently show they face heightened barriers to care. This ranges from transportation and scheduling conflicts to language access and opaque billing systems. While many direct-to-consumer health platforms target commercially insured users, Twentyeight has chosen a more complex path, and doing so, is proving that trust can be built in the most fragmented corners of the healthcare system.

Fintech as a Bridge, Not a Bolt-On

One of Twentyeight Health’s early insights was the need for flexible payment methods. “We accept prepaid debit cards, flexible savings accounts, and even cash-like payment methods. Meeting people where they are is key,” said Castro.

What sounds like a simple operational choice is actually a powerful signal. Platforms like Twentyeight must think not just about who they serve, but how those users transact. Embedded finance—through instant payments, earned wage access, or installment billing—has already reshaped consumer commerce. Yet in healthcare, most fintech innovation has stopped short of the real bottlenecks: affordability, reimbursement, and compliance.

That opens up white space. Imagine if digital health platforms enabled sliding scale payments, automated Medicaid copay lookups, or used BNPL infrastructure for procedures not covered by insurance. The same rails powering Afterpay and Klarna could be leveraged to reduce the significant portion of patients who delay or forgo care due to cost.

Castro noted, “Fintech integrations will be part of how we scale, especially for services that aren’t reimbursed. We have to make payment as frictionless as possible.”

Twentyeight’s Next Chapter

Twentyeight has always operated at the intersection of equity and innovation, serving patients often excluded from traditional healthcare—particularly Medicaid-eligible and uninsured women. Now, as demand for GLP-1 medications, medical-grade skincare, and digitally delivered care surges, the company is entering a new phase of mission-driven growth.

Today Twentyeight is announcing the launch of its Personalized Care Program, expanding beyond reproductive health into:

• Get Care Now: fast, low-cost prescriptions for common women’s health needs;
• Weight Care: a GLP-1-based weight management program with on-demand provider support;
• Skin Care: subscription access to prescription-grade treatments for common skin concerns.

This expansion reflects both rising consumer demand and a continued focus on affordability, with services starting at $17.99/month.

In many ways, this is a natural evolution of the company’s long-term vision. And as fintech tools like installment billing and real-time eligibility checks become critical enablers of care, Twentyeight offers a blueprint for how healthcare can scale with empathy, trust, and accessibility at its core.

As Castro observed, “There’s so much talk in digital health about scale, but very little about sustainability. If your users can’t afford what you’re offering, scale becomes irrelevant.”

For both founders and investors, the implications are clear: the future of care is inclusive, distributed, and financially attuned.

The Takeaway

The intersection of fintech and women’s health remains underexplored, but the connections are profound. As platforms like Twentyeight Health earn trust at the margins, they are crafting a new standard for care that is both accessible and human-centered.

For those building in either ecosystem, the message is simple: design with empathy. Prioritize usability. And never underestimate the impact of giving patients a way to pay.