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- Nikita Singareddy, Co-Founder and CEO at Fortuna Health, on building in Medicaid
Nikita Singareddy, Co-Founder and CEO at Fortuna Health, on building in Medicaid
An interview with Fortuna Health's CEO discussing a variety of topics related to Fortuna's model and the Medicaid market more broadly
Kevin O'Leary & Martin Cech
July 21, 2025
This morning, Fortuna Health announced a $18 million Series A funding round led by a16z. Check out the funding announcement here. Given the momentum they have building in the Medicaid market, we thought it’d be fun and informative to ask Fortuna’s Co-Founder and CEO Nikita Singareddy a few questions both about how Fortuna is building in Medicaid and about the broader Medicaid landscape.
Below is some background on why we find this space so interesting, the list of questions we asked Nikita, and then the full interview. We hope you enjoy learning from her as much as we did!
- Kevin and Martin
Background:
Medicaid is the payer for over 78 million Americans, ranging from newborn infants to seniors who are dually eligible for both Medicare and Medicaid. It’s larger than both Medicare and the largest private insurer, UnitedHealthcare, and covers patients in all fifty states, the District of Columbia, and 5 overseas territories.
But talking about it as one large health plan is misleading. Since its inception, Medicaid has operated as a set of laboratories for health care policy and financing in each of the 56 departments that run it at the local level. The long leash afforded by the Centers for Medicare and Medicaid Services also creates incredible complexity with 56 different processes for proving you’re eligible for benefits, 56 processes proving you’re still eligible for benefits when it’s time for redetermination, and a near constant swirl of rules and regulations coming from state and federal legislatures as well as the CMS administrator.
Although it’s been historically overlooked by venture investors, that’s starting to change. Companies focused on Medicaid raised blockbuster 9-figure rounds back in 2022: Cityblock (SoftBank, $400m) and CareBridge (OakHC/FT, $140m), along with more recent raises from Waymark (Lux Capital, $40m) and Eleos (Greenfield Partners, $60m). But these startups are mostly focused on care delivery and coordination, and one of the biggest challenges in Medicaid is just getting people who are eligible signed up.
Arguably, the largest player in the eligibility and enrollment space today is Deloitte, with contracts worth over $6b in 25 states, although these contracts have garnered criticism for costly errors, slow response times, and eligible patients getting caught with no insurance. It’s a “now more than ever moment” because we’re in the quiet center of a double-dip crisis in Medicaid enrollment between the end of the COVID-19 public health emergency which triggered a huge wave of redeterminations and the recently signed One Big Beautiful Bill Act which is changing the Medicaid eligibility criteria in the most significant way since the Affordable Care Act was passed.
To learn about building for Medicaid members and what the new One Big Beautiful Bill Act means for patients, providers, and startups in the space, we spoke with Fortuna Health’s CEO Nikita Singareddy.
Questions
Interview
Q: What is the problem that Fortuna solves for its users? What does a beneficiary have to do to get enrolled in Medicaid normally, and how is it different with Fortuna?
Fortuna helps consumers navigate Medicaid and government coverage from start to finish: understanding eligibility, completing enrollment, renewing coverage, and transitioning off the program.
For most beneficiaries, these processes are far from straightforward. Eligibility criteria vary by household, state, and program. Enrollment can be confusing and multi-step. Once enrolled, maintaining coverage requires staying on top of renewals, income updates, and administrative follow-ups - tasks that are prone to error and delay.
This isn’t just a UI issue, though design plays a role. The core challenge beyond complexity is that Medicaid administration is fragmented:
Many eligibility systems are outdated and error-prone. 44 states run systems over a decade old, while 13 states maintain two concurrent platforms.
Eligibility and case management practices differ widely. Processing can be inconsistent - especially when states and counties are under-resourced.
Data verification systems are incomplete or mismatched, and follow-up actions are often manual and opaque.
Fortuna is modernizing that infrastructure to proactively guide beneficiaries through each step, preventing common failure points, and maintaining continuity across different systems and time periods. We see this in service of supporting states with greater accuracy and timeliness in eligibility and enrollment (E&E), reducing administrative burden while strengthening program integrity and improving the overall experience for beneficiaries.
Q: Who pays for Fortuna? Is it the state agencies or Medicaid Managed Care plans or providers who see these patients?
Largely payers and providers. These are the organizations that are most directly impacted when individuals face coverage challenges.
In states without significant managed care penetration, we work with health systems. These are often the frontline providers for Medicaid beneficiaries and bear the financial and clinical consequences when coverage lapses. For them, helping patients gain and maintain eligibility isn’t just a compliance issue - it’s a business and care delivery issue especially in rural areas.
Q: Medicaid operates differently across the 50 state agencies, the District of Columbia, and the territories, and there are experiments, waivers, and state regulations. Is your goal to cover the entire geography, or are you focused on the biggest markets? How do you prioritize what markets to enter, and what do you need to have in place to ‘launch’ in a market?
Our goal is definitely to support all 56 Medicaid programs across states and territories. That almost feels like table stakes if we position ourselves as “TurboTax” for Medicaid. Early on, we tried to identify ideal states for launch based on administrative characteristics, but there’s no perfect starting point because every state is very different.
Now, we prioritize based on demand. If a provider or payer partner has a need and we believe we can deliver value, we’ll invest in standing up that state’s requirements. Over time, that’s how we’re building toward national coverage.
Q: Churn is very high in Medicaid. MacPAC reported in 2018 that 21% of Medicaid enrollees churned (15 million people) while 8% churned and then re-enrolled within 12 months (5 million people). How would you articulate what needs to change to reduce that number? Is the system just too complicated? Are there underlying structural problems? Something else?
Churn is driven by a mix of structural complexity and operational fragmentation. Medicaid and government program eligibility isn’t static. People’s income, their benefits, household situation, and work/employment change. But the systems tasked with keeping up are often rigid or out of sync. A renewal form goes to the wrong address, or an income record can’t be verified, and coverage ends - even when an individual and their household still qualify.
What makes churn hard to solve is that it’s an accumulation of things:
Outdated infrastructure and confusing user experience.
Caseworker capacity constraints and inconsistent processing.
Mixes of paper-based processes with digital (i.e., portals, faxing), depending on the action.
Limited and lacking sources of verified data.
Improving accuracy, promoting efficiency, and stabilizing churn means investing in more resilient infrastructure. I think that happens with a mix of policy choices and technical improvements.
Q: Fortuna raised its seed round just a few months after the redeterminations started post-COVID-19 public health emergency. Can you talk about navigating that huge wave of work as a nascent company?
No doubt that the COVID-19 unwinding surfaced longstanding fragility in Medicaid infrastructure. We saw tens of millions of people pushed through administrative processes that hadn’t been stress-tested in years.
Honestly, we were too early. Fortuna was still small, and we hadn’t yet built the product we have today. But the unwinding confirmed our core thesis: that E&E is one of the most underappreciated, yet highest-leverage, opportunities in Medicaid. When coverage is accurate and stable, everything downstream - value-based care, risk adjustment, quality, case management - works better. Not just for states, plans, and providers, but for the people they serve.
Rather than focusing on sales during that period, we doubled down on product. As outsiders, we had to go deep on the rules, workflows, compliance, and edge cases to build a navigation product that could actually scale.
That conviction and foundation have served us well.
Q: You’ve described Fortuna as the "Turbotax" for Medicaid, which is a great description since, like the US tax code, Medicaid eligibility is incredibly complex and needs a friendly interface. But Turbotax has also been criticized - whether fairly or not – for inserting itself between the government and its taxpayers and then fighting off efforts for the government to build capacity and make its interfaces easier. Fortuna Health is a venture-backed company, which inherently comes with the expectation of generating meaningful financial returns for investors. How are you navigating the tension inherent in being a private for-profit company attempting to make accessing government services easier?
We use the “TurboTax” for Medicaid analogy because it's a useful shorthand for what we’re building - turning a complex, high-stakes process into something accessible and user-friendly. Unlike TurboTax, Fortuna follows a B2B2C model that allows us to be funded but free to consumers.
Healthcare has many examples of consumer-focused models supported by the broader ecosystem. Zocdoc and GoodRx are strong D2C businesses where the end user doesn’t pay (their value is supported by providers or pharmaceutical partners). We see our approach in line with services covered by health plans, like Maven, Pomelo, and Nourish, as a product that supports member engagement and health outcomes.
Q: Among the ~25 million uninsured people in the US, ~25% of them are eligible for Medicaid but not enrolled?-- is this who you see as your ideal user? How else do you think about segmenting the market? Are you focused on the expansion population or Medicaid beneficiaries in total, including dual-eligibles, children and caregivers, and adults with disabilities as well?
Fortuna was built to be flexible across the Medicaid journey: eligibility, enrollment, renewals, and transitions. The users who benefit most from Fortuna are often those facing friction due to complex household situations, inconsistent or hard-to-verify income, or challenges understanding what’s required and how to follow through. If someone has a straightforward path through Medicaid, they might not need us.
Right now, our product and automations serve a large number of Children’s Health Insurance Plan (CHIP), Temporary Assistance for Needy Families (TANF), Modified Adjusted Gross Income (MAGI), and MAGI expansion beneficiaries, including caregivers and working families. We've spent less time on dual-eligible populations to date, as their enrollment and renewal processes differ significantly. It is a segment we’re preparing to support more directly with our Series A raise.
Q: You recently commented on a LinkedIn post that stated this: “Give me an agentic AI which does instant, seamless Medicaid redetermination in all 50 states. If AI can't do this yet, explain why it can do everything else but this problem is too hard. Then explain to me why if it's too hard for generative AI, we expect poor sick people to do it on their own.” It seems like a reasonable question to be asking. I’d imagine this isn’t the first time you’ve heard pushback about the complexity of various state requirements. But it’s hard for me to understand why exactly it’s all so complicated – like I don’t intuitively understand why we need AI to determine if someone is eligible for Medicaid in their state. Could you shed some light on why this is all so complicated to implement from a practical perspective?
I completely agree with the spirit of the question. If AI can do things like drive cars and write code, why can’t it handle something like Medicaid redeterminations? AI is valuable. We use it. But it doesn’t solve many root issues - fragmented systems, inconsistent processing logic, unclear follow-up steps, and the absence of real-time feedback loops. You can’t just run the eligibility manual through a model and expect it to work. We’ve tested that theory.
We’ve spent significant time working with states and counties. That work - building relationships, understanding how policy gets operationalized, and seeing the practical and technical constraints up close - has been essential. You can’t solve Medicaid by staying abstract. And you definitely can’t solve it with AI alone or without the systems context and trust that comes from working in partnership with the government.
Q: What sort of competition do you see for Fortuna? We’re aware of non-profits like MyFriendBen as well as companies like Healthy Together and Cedar that are working in the space. When you’re talking to state agencies or MCOs about adopting Fortuna, what do you find they’re evaluating you against?
Nonprofits and navigation groups have long played an important role in this space. One of the reasons we chose not to be a non-profit came from the belief that serving beneficiaries at scale requires stability. We didn’t want to risk grant funding challenges. We’ve also seen what happens when impactful non-profits, like Benefits Data Trust, shut down. It’s a loss for the whole ecosystem.
When plans evaluate us, we often hear names like BeneLynk and Centauri. These are primarily call center models that operate across multiple programs, including VA benefits, SSI/SSDI, and more. That broader approach works for some, but we’ve made a deliberate choice to stay focused on Medicaid with technology as our foundation. Getting this right takes precision and focus.
That focus also creates room for strong partnerships. Take Cedar, for example. We closely partner with them on Medicaid eligibility, enrollment, and renewal, integrated into Cedar Cover, an affordability product suite designed to help health systems maximize reimbursement and expand patient coverage. It’s a good example of how we collaborate to bring our infrastructure to where it’s most needed.
Q: Deloitte has faced some negative publicity recently about the $6 billion in Medicaid contracts it has with 25 states to manage their eligibility systems. It seems those systems are riddled with errors, but Deloitte points back to the states because of the numerous changes they attempt to make to the platforms. How would you articulate the underlying challenge here, and why is a startup like Fortuna able to improve on this?
Medicaid can sometimes feel like the Spider-Man meme, with everyone pointing fingers. Both of these things can be true: vendors build poorly-architected systems with errors and face shifting requirements from states. That’s exactly why modernization and empathetic collaboration are so needed.
A little history: Medicaid and CHIP systems were originally built as large, monolithic welfare system platforms. About 10 to 15 years ago, there was a push toward modularization. But with turnover on both the state and vendor sides, it’s often hard to sustain alignment and drive projects to completion.
This moment calls for something different. Many vendors in the space aren’t true tech companies. They outsource engineering, treat delivery as a checklist, and often drive unnecessary complexity and cost - contributing to the very waste and inefficiency that policymakers and CMS are trying to fix.
Meanwhile, companies like TurboTax, LegalZoom, and Plaid have shown that even the most complex, rules-heavy systems can be made modular and user-friendly. Medicaid deserves the same.
Q: Medicaid has historically been an under-invested thesis when it comes to venture-backed tech companies, but there are some signs that that’s changing. What’s your hypothesis for why that’s the case?
I think it largely comes down to two things: first, the rise of Medicaid managed care, and second, investors starting to really learn about Medicaid.
As managed care took hold in 40+ states, it created a new class of buyers - plans and providers who aren’t the state but are still responsible for delivering on state contracts. That shift created demand for services and tools that help meet member needs, close gaps, and manage performance.
On the investor side, there’s been a slow but meaningful learning curve. A decade ago, you started to see companies like Unite Us and Cityblock get backed by people who deeply understood Medicaid like Town Hall Ventures. As investors learned more, we started to see more companies funded around Medicaid-specific priorities: Pomelo Care in maternity; Summer Health and Imagine Pediatrics in pediatric care; Boulder Care, GROUPS, and Wayspring in substance use treatment; and Abby Care and CareBridge in long-term services and supports (LTSS). These aren’t broad, generalist health tech plays. That shows me that investors aren’t just aware of Medicaid now, they’re building conviction around it.
Q: As you look around the market, what are the things that are still missing when it comes to Medicaid healthcare technology? What do you wish existed for your members?
There’s still an enormous opportunity to improve long-term services and supports. Home and Community-Based Services (HCBS), in particular, remain complex and difficult to navigate. That space is deeply personal to me - my aunt has a severe developmental disability - so I feel a moral imperative for companies and technologies to focus here.
Q: The big change for Medicaid eligibility in the recently passed One Big Beautiful Bill Act seems to be the work and community engagement requirements. For a beneficiary, what do these work or community engagement requirements mean? How is Fortuna adapting this into its workflows?
These requirements primarily apply to able-bodied Medicaid expansion populations and generally mandate 80 hours a month of work or community engagement. Propel has a great write-up on this. The reality is, most beneficiaries are already working or qualify for exemptions. The challenge is documentation and connecting beneficiaries to work/community resources.
For people in stable, hourly jobs, states may be able to handle this through ex parte verification (HTN note: see this CMS document for an explainer on ex parte verifications). But 46% of jobs that enrollees have don’t consistently show up in the Federal Data Hub or in The Work Number.
We’re focusing our workflow development for this population - those most likely to struggle with verification due to self-employment, multiple jobs, cash/tip pay, seasonality, and overtime variability. Our goal is to build flexible infrastructure that can adapt to the way different states choose to design and implement these policies. Any company claiming they’ve already solved for work requirements is overstating what’s possible at this stage.
Q: These aren’t new conceptually-- 13 states got waivers to do this during the first Trump administration, though they got rescinded during the Biden administration. Georgia is the exception, and from what I’ve read, enrollment has fallen short of the government’s goals, and it’s been pretty expensive. Are you doing any work in Georgia, and can you help us look into the future a little and see what this will mean for beneficiaries in other states?
Georgia’s implementation struggles are a useful case study in the complexity of work requirements. Standing up any new Medicaid program requires both operational and technical adaptability. So when something isn’t working, as appeared to be the case in Georgia, that's the time to pivot.
States like Colorado and Tennessee have issued RFI/RFPs that show how top-of-mind ex parte verification for work requirements really is. But most are still sorting out the operational and technical details. We’re watching this closely and thinking about how our work and infrastructure can support states as they define their approach.
And yes, stay tuned - we may have something brewing in Georgia!
Q: There are roughly 71.4 million people on Medicaid, but the work requirements are specifically for the Medicaid expansion population. Surveys of Medicaid enrollees tend to show that there aren’t that many adults who aren’t in school or working, but the CBO expects that of the ~18.5 million people who are subject to the work requirements and 5.2 million of them will lose their coverage by 2034. What’s driving the outsized losses of coverage?
In short: paperwork. That’s not because these beneficiaries don’t meet the requirements, but because they won’t successfully complete the paperwork or navigate the verification process.
There’s also collateral damage. If the head of household loses coverage due to a paperwork issue, it can jeopardize coverage for the entire household like children on Medicaid or CHIP.
Q: Another one of those changes is that the redetermination cadence is going from every 12 months to every 6 months. For readers who haven’t experienced a redetermination, what does that look like from the perspective of a beneficiary? And what about from the State, MCO, and provider perspective?
Whether it happens every 12 or 6 months, redetermination starts with the system flagging that someone’s coverage period is ending. That triggers a notice to the household. Some beneficiaries in the household may be renewed automatically through ex parte processes. Others are asked to take action - typically within 60 days.
That action might include logging into a state portal, returning a mailed form, faxing in documentation, or scheduling a phone or in-person appointment. Enrollees have to confirm income, household, address, job status, other benefits, medical conditions - anything that could affect their eligibility. Often, they have to submit proof.
Plans often know when members are up for renewal through membership data feeds. Many will use that window to notify members directly or point them to resources like Fortuna.
Q: A theme we’ve heard a lot about with this administration is trying to reduce waste, fraud, and abuse, and there’s also some language around “Verifying Enrollee Address and Other Information” which seems mostly about confirming a beneficiary isn’t enrolled in two states at the same time and cross-checking beneficiary lists with master death files. Are there opportunities here for Fortuna to be a source of truth for Medicaid agencies?
CMS isn’t wrong that there are real FWA issues, including improper enrollments and disenrollments. There’s a big opportunity here to use modern technology, verified data sources (like USPS address matching), and MCO data to help states keep their records accurate.
Enrollment in two states or more is a concern, especially when people move (and every state saw erroneous cross-enrollment in 2024). States rely on retroactive matching through the PARIS system, but there’s an opportunity for more real-time solutions. One example is fixing duplicate enrollments in states where Medicaid/CHIP are split from state-based ACA exchanges (like KY and NV). Some enrollment bottlenecks are operational. Many counties - especially in the 26 states that delegate some of Medicaid administration to local departments of social services - are underfunded with paper-heavy processing. That makes timely disenrollment and updates difficult.
We’ve always built Fortuna with universality in mind. So we’d love to offer our operational perspectives and technical resources to step up as a source of truth.
Q: The Affordable Care Act was mostly known for the health insurance marketplace, though Medicaid expansion was in many ways a larger part of it. More than a decade later, with the enhanced subsidies for plans bought on the exchanges set to expire and ACA plans just not being that attractive a business for a lot of folks who’ve tried, we’ve heard people speculate that Medicaid is going to grow in size, scope, and importance. What’s your view on this?
I agree with that view. The ACA is entering a period of real strain - limits on silver loading, new documentation requirements under OBBB, and the likely expiration of enhanced subsidies. We're already seeing payers signal higher costs on exchange plans, and those impacts will be especially felt in non-expansion and farm states where many people rely on ACA plans.
States do have several tools - State Plan Amendments (SPAs), 1332 waivers - to build affordability models around the ACA, but I don’t think that will stop the ACA from contracting. Alongside several states that have codified Medicaid access and funding directly into their constitutions, I agree that Medicaid will become increasingly central to the healthcare safety net.
Q: There has been some discussion about the potential to combine Medicaid, CHIP, and the ACA into one national exchange in the future. See, for example, this recent article from Ezekiel Emanuel. Do you view potential policy changes like that as an existential threat to Fortuna’s business? i.e., if there were major structural changes to the Medicaid program that resulted in coverage determinations moving from the state level to the national level, it seems like it could potentially minimize the need for this sort of work moving forward. If a political leader were asking you to advise them on potential structural changes such as this, what would you encourage them to think about?
That’s an intriguing idea. I don’t see it as an existential threat, but I’d offer a few things for policymakers to consider.
First, it’s true that U.S. healthcare has evolved as a patchwork - Medicare, Medicaid, CHIP, and the ACA were each layers built to close a different coverage gap. Not necessarily bad, but certainly complex with various horsetrading and compromises between government bodies. So yes, I understand the desire and agree with goals to streamline, reduce duplication, and improve accuracy with a unified source of truth.
That said, the strength of Medicaid and CHIP has always been that states can tailor their programs to meet the needs of their populations. Rural composition, population demographics, provider availability - these vary dramatically across states. And so does the supporting tech and delivery infrastructure. Any effort to centralize needs to be careful not to lose the value of local adaptability and state ownership.
Q: A trend we’re seeing at the state level is trying to get better at the coordination of benefits. Are things like SNAP and cash assistance areas where Fortuna is interested in in the future? Is there an opportunity here to connect some things that are in the universe of “Social Determinants of Health”?
What matters most to us is building a product that delivers long-term value to Medicaid consumers. What’s high on a policy roadmap isn’t always what people need or ask for. So never say never, but that’s not where we’re focused right now!
On our product philosophy: I love the example of Zola. They started with wedding registries, then thoughtfully expanded into invitations, venue discovery, vendor scheduling, honeymoon planning, and eventually baby registries. Great products understand the full journey and know how to introduce the next step - the feature that adds real, incremental value for their users.
For Fortuna, that means continuing to build features that support the full journey of navigating Medicaid and government coverage. That could mean helping schedule a well visit for a child, surfacing rent support through a plan’s value-added benefits for a working family, or connecting someone to job training as they transition off Medicaid. Different life stages bring different needs - and our goal is to meet Medicaid enrollees where they are.
Q: We’ve heard a lot from public Medicaid and Medicare Advantage insurers over the past several earnings calls discussing the dual special needs market and states increasingly looking to integrate Medicare and Medicaid offerings. Many of these payors seem to think that this integrated approach from the states will be a boon to their business. How do you think this evolution will impact the market and your business?
It’s a major shift, and I think it will be a net positive for Medicaid-focused plans. States are under federal timelines - most aiming for high levels of Medicare-Medicaid plan integration by 2027, and full alignment by 2030. That’s driving strategic moves across the industry as the Medicaid plan is the anchor for these changes. Just look at Humana’s entry into Medicaid through state RFPs; they clearly see protecting their duals population as essential.
For us, we’ve always been Medicaid-first. So we’re well positioned to support duals populations as integration deepens.
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