Lessons from Michael Roaldi, President of Cityblock, on improving engagement, trust, and access to deliver high-quality care
This episode is part of Pear VC's series on Medicaid, covering the basics that founders need to know to build innovations that support communities in need.
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This series aims to demystify Medicaid, starting with insights from federal and state agencies, FQHCs, and managed care organizations, before exploring successful founders' strategies. Read our primers on the key players and innovations here, and stay tuned for upcoming posts featuring interviews with key opinion leaders, purchasers, and startup founders.
This week, we're excited to get to know Mike Roaldi, the new President of Cityblock Health.
Cityblock Health is a value-based healthcare provider focused on the complex clinical, behavioral health, and social needs of dually eligible and Medicaid recipients. Cityblock offers the only fully integrated and multi-modal solution that directly delivers clinical care to one of the most at-risk and hardest-to-reach populations. Powered by advanced technology that provides its care team with a data-driven understanding of member needs and risks, Cityblock has demonstrated industry-leading engagement, member retention, meaningful reductions in avoidable hospital readmissions, and reduced total cost of care.
Founded in 2017, spun off by Sidewalk Labs, and based in New York, Cityblock has raised nearly $900M to date from investors such as SoftBank, Tiger Global, Maverick Ventures, General Catalyst, Thrive Capital and 8VC, among others. It is now valued at $5.7B. Cityblock currently serves more than 100,000 members, and partners with four national Medicaid health plans and several health systems in 15 cities across seven states.
Mike's career has spanned both legal and healthcare leadership roles, starting as a commercial litigator before joining UnitedHealth Group as National Vice President of Medicaid Policy and Product. He went on to serve as CEO of UnitedHealthcare Community Plan of Ohio, then as Chief Transformation Officer and President of Government Programs for Optum BH Solutions, and later as Chief Growth Officer and SVP of Growth and Product at UnitedHealth Community and State. In 2024, he joined Cityblock as President to help drive the company's next phase of growth.
Mike holds an undergraduate degree from the University of Notre Dame, a JD from Notre Dame Law School, and attended an Executive Education Program at Stanford Graduate School of Business.
In this episode, we learn about how health plans evaluate startups, the complexities of improving access for Medicaid and dual-eligible populations, and Cityblock's innovative approach to building trust and engagement.
Here is the recording if you would like to listen!
Background
Mike’s background in Insurance
Mike joined UnitedHealthGroup in 2015 during a period of increased government focus on social determinants of health (SDOH). His role was to understand how insurers could effectively address SDOH. From an operational, ground-level perspective, he investigated the administrative challenges in addressing these needs, particularly for Federally Qualified Health Centers (FQHCs) that depend on multiple funding sources.
Insurers often struggle to grasp the complexities of care delivery, including both the financial constraints and operational capacity limitations that hinder addressing these challenges.
Initially, as an insurer, he had assumed that simply connecting social services with healthcare would create a holistic healthcare experience. However, the reality proved far more complex.
Bridging National Strategy with Local Care
In 2019, Mike transitioned from his National VP role to become CEO of the Community Plan of Ohio—a position he took on during COVID. This experience taught him valuable lessons about the stark differences between working at the national versus regional level.
His experience in both roles exposed valuable bilateral synergies. At the national level, he gained expertise in claims payment systems and care management protocols. At the regional level, he had the advantage of hearing directly from the community and became responsible for advocating their needs to the national team.
“Startups are often able to make some inroads with national plans by being responsive to a local market’s needs, a local health plan CEO’s needs. Once they demonstrate their effectiveness [at the local level, they can] start to identify needs that are common across markets so that the health plan CEO can recommend them to their national team.”
This experience also taught Mike that there is a balance between standardization and customization of care. While standardization provides cost efficiencies across markets, it can sometimes be less responsive to local needs.
Mike's role involved understanding local demands and deploying the resources of a larger enterprise—a responsibility that became particularly critical during COVID.
For example, during COVID, they needed to adapt and lift certain care delivery restrictions that were no longer relevant, especially regarding telehealth.
He also took on the critical role of informing national leaders about local innovations and unique provider initiatives that warranted scaling. For instance, when he discovered a hospital system implementing an especially effective disease management program, he would explore opportunities to scale it to other markets.
Health Plan Approaches to Growth
After leaving Optum where he focused on Behavioral Health, he transitioned to a role as Chief Growth Officer/SVP Growth and Product at UnitedHealth Community and State. In this role, he was responsible for growing membership.
Plans in the dual and Medicaid space need to recognize that excellent service to members is essentially table stakes for continued growth. For Medicaid plans, excellent service is essential to win procurements as an MCO through various RFPs from state Medicaid agencies.
Medicaid MCOs typically have network adequacy requirements for their provider networks. They must legally maintain sufficient providers so members can access care within specific time and distance parameters.
Within these RFPs, there has been greater focus on increasing access to care. This goes beyond the typical regulatory network adequacy requirements imposed on Medicaid MCOs. Mike is referring to making care more accessible for people who may not proactively seek it.
In recent years, insurers have focused heavily on benefit navigation, making substantial investments in digital tools with various interfaces to help consumers better understand their benefits.
Plans attempt to build these capabilities internally while also partnering with external providers and startups. However, since health plans can't move as quickly as startups or invest in more speculative ventures, they often use the startup community as incubators for innovations they want to explore but can't develop themselves.
“Sometimes ongoing dialogue with insurers about what their needs are can be helpful. Any founder who has access to the insurer community should regularly solicit that feedback to help develop their business thesis.”
Medical Loss Ratio (MLR) is a key performance indicator for health plans, measuring the percentage of premium dollars spent on medical care and quality improvements rather than administrative costs. With regulatory requirements to maintain an MLR of 80-85%, insurers actively seek solutions that help control medical costs.
Mike distinguishes between vendors and new provider types. Health plans generally are more excited to work with providers who offer novel medical services rather than pure vendors who don't deliver direct medical value.
Advice to Startups
As a health plan growth officer and CEO of a regional plan, Mike frequently evaluated pitches from innovative startups seeking to sell their products. Drawing from this experience, he offers valuable insights to help founders better communicate with insurers.
What makes a good vs. bad pitch from a startup?
“Simply: facts. What distinguishes a startup is their ability to not just show outcomes data but unpack how they are able to get to the outcomes that they are talking about”
Mike notes that while many startups share compelling stories, the most important thing they can demonstrate is not just improvements in cost, inpatient stays, or quality metrics—but their actual theory of change and exactly how they achieved these results.
Health plans struggle to differentiate between startups amid the flood of statistics and often question their credibility. Companies can build confidence in their operational discipline by clearly describing how they achieve results, including specific details about their tech stack, interventions, behavioral science approaches, or experimental methodologies. This helps overcome the common bias that startups may not be able to deliver.
For each strategy, it's valuable to demonstrate the incremental uplift it provides—this concrete evidence helps truly differentiate startups from their competitors.
“If you’re going to show major quality improvements as part of your offering, be ready to describe more than the high-level strategy. Be willing to talk about staff, backgrounds, mode of outreach, and what you see in terms of uplift for each of those.”
On effectively communicating success
Mike suggests being parsimonious with words but detailed with metrics. Being direct and clear about the intervention helps payers understand the core elements of your tactical approach. However, he recommends providing even more granular metrics than what you typically see in an average pitch.
“When you provide a high-level number of inpatient admission reduction, [plans will start with the] assumption that there’s some level of regression to the mean. So how do you really show that it was your intervention, your work, that led to that change? This requires breaking down the metrics so you can show actual causality.”
It's really important for startups to show that their intervention caused the improvement rather than regression to the mean (for instance, finding the patient at the most acute point in their health journey when they were statistically likely to be admitted less frequently afterward).
You can start by showing the average treatment effect against the counterfactual—the difference between people engaged in a particular intervention and those who have not.
Engagement vs. Outcomes
“Many of the activities that you need to do in order to proactively engage the population are not reimbursable. They are not traditional medical services.”
Mike sees engagement as a prerequisite to outcomes. Engagement itself has value because it's a platform for providers to demonstrate value to insurers. At Cityblock, Mike and team put a huge emphasis on engagement. However, at the end of the day, plans want to know how you can convert that engagement into meaningful care delivery interactions.
For startups that struggle with justifying the cost of non-medical engagement (which is not typically reimbursed or reimbursed well), Mike offers the following guidance on financial arrangements he's seen plans adopt:
Administrative Fee: PMPM—a set fee per member per month.
Administrative Fee: PEPM—a set fee per engaged member per month, which is typically easier to justify to plans since patient engagement is guaranteed.
State or Federal Grant Funding (similar to a patient-centered medical home).
Shared Savings Risk Arrangement, which is ideal but challenging without established engagement capabilities. In rare cases, payers may offer cash flow advances on downside risk to help providers build their outreach function.
Effective Sales Strategies
“The best thing to do is have a relationship with the health plan leader long before you ask for anything, even if it’s asking for career advice or just getting to know that person.”
Mike offers the three most effective sales strategies that he's seen in his time on the purchasing side of healthcare:
Developing a relationship long before you're ready to pitch a product or request a risk contract.
Using that relationship to understand the insurer's biggest needs and gaps while approaching it as a partnership. Leveraging the relationship to sound out your core business hypothesis with the health plan leader.
Focusing on substance over style. Clearly articulating your product's facts and connecting them to the specific tactics that delivered your metrics.
Health plan relationships with new technologies
Most health plans are fairly comfortable embracing new technologies. If there is an issue, it typically stems from legal and regulatory perspectives.
Startups can manage this by demonstrating how they've assessed the legal and regulatory risks.
They can also consider white-labeling digital solutions and adopting the payer's branding.
They should also consider how to integrate with the health plan's existing offerings without creating confusion for members who might already have dozens of apps and want to simplify their access to care.
Cityblock
Cityblock’s Mission
Cityblock is an advanced primary care provider—with some specialty care capabilities—serving Medicaid and dual-eligible members. They are healthcare providers dedicated to improving care accessibility for underserved communities.
Cityblock stands out for its proactive patient engagement approach. Through investments in multiple care modalities—brick-and-mortar clinics, in-home care, and virtual care—they deliver healthcare wherever patients need it.
Dual-eligible individuals, or "duals," are people who qualify for both Medicare (typically due to age or disability) and Medicaid (due to low income and resources). These beneficiaries often have complex healthcare needs and face unique challenges navigating between the two programs' different benefits, networks, and coverage rules.
Dual-eligible beneficiaries face greater barriers to care than typical Medicaid recipients, including disabilities and challenges with activities of daily living (ADLs).
For DSNP members, the split between Medicaid and Medicare benefits creates confusion when determining which network covers their services. The complex policy and regulatory framework makes navigation even more difficult.
Cityblock simplifies this process by taking on patient risk, removing the burden of figuring out how to access care.
Cityblock on Access
“[Network adequacy requirements] are useful but limited in how much they measure actual access to care. All they check is if a person decided they wanted care (and had a means of getting to that care) how long it might take them. But we know there are more layers to access.”
Cityblock thinks about access in a more holistic way. Mike describes below some of the barriers that their population faces:
Even when providers are in-network, they may not have appointments available
Members may struggle with transportation, work schedules, and childcare
Cityblock's ability to deliver care through multiple modalities helps overcome these obstacles. Virtual care provides a great option for those without immediate access to transportation. For episodic needs, they can deploy mobile integrated care teams of paramedics to patients' homes. And because their clinics are value-based rather than fee-for-service, doctors aren't limited to 15-minute appointments—they can spend the time needed to address not just clinical problems but also patient education and social determinants of health.
Cityblock represents how Mike might have designed a provider from scratch—one that improves access by design.
Cityblock on Engagement
Cityblock takes a highly personalized approach to member engagement. This strategy enables them to achieve engagement rates significantly higher than industry standards.
“Each individual member has a different risk profile, a different preference for how they communicate and so we take that and build an individualized engagement strategy. And then we are persistent. And we also have a mechanism for continually learning.”
Cityblock's individualized engagement strategies stem from their strong behavioral economics function that consistently evaluates which interventions are working and which are not (including the timing and method of outreach). For example, they might see a 2-3% increase in engagement from simply changing the content of an initial mailer to members. As Mike shares, "That's worth it. That’s replicable." At scale, these changes can add up over time and compound into a much higher engagement rate.
Another strategy that Cityblock uses is priming—preparing members by providing information before they call or visit their house to prevent skepticism about potential scams. This helps establish Cityblock as a legitimate care delivery organization and ensures subsequent messaging is responsible and culturally appropriate. Their approach extends to tailoring language capabilities to best resonate with native speakers.
“Engagement is just the beginning. In order to actually help with delivery of care, to encourage folks to seek care, we have to establish some level of trust in that initial interaction. So we don’t really ask for anything when we first reach a member, we don’t try to close a gap in care or do an assessment, we offer something instead.”
Most importantly, Cityblock measures trust. In the first interaction, they typically don't ask for anything—they just try to establish an initial level of trust by offering something the member needs. This approach leads to not just high engagement rates but also high conversion-to-care rates. They have a proprietary trust index (beyond just NPS) that measures their level of trust with each member, allowing them to measure and focus on interventions that improve this metric.
Why did you join Cityblock?
Mike was most drawn to Cityblock's commitment to operational discipline and rigor. They also appealed to him because they continuously learned from their mistakes. Given Cityblock's approach to access and engagement, Mike believes this is the closest thing to what he might design from scratch.
Mike joined Cityblock because he recognized the potential impact they could have by scaling their current interventions. He also saw an opportunity to help unlock a larger market.
Finally, Mike and Toyin have a strong relationship—he views her as incredibly compelling and passionate, and he was excited about the opportunity to work closely with her.
Cityblock’s funding history
Cityblock was a pioneer in its time, and the significant buzz around it helped secure $900M in capital throughout its lifetime. This capital has allowed Cityblock to build out the structure underneath its vision, as outcomes-driven change in this population requires sustained, long-term effort.
The capital infusion has enabled them to build out the capabilities they've developed while experimenting with different engagement strategies.
It also allowed them to develop advanced care pathways to properly serve specific needs within the population. The later rounds of funding have helped them mature as a company and strengthen their operational discipline.
Key Levers for Cityblock
Mike notes that the top lever driving outcomes is maximizing the first interaction with the member to develop trust. While many assume they should use initial phone contact to conduct needs assessments, close care gaps, or schedule PCP visits, Mike emphasizes that investing in trust-building yields better long-term results.
The second key lever is mobile integrated care capability. For patients who struggle to access care, especially during urgent situations they couldn't plan for, Cityblock can dispatch a mobile integrated care team directly to their home. These teams can connect with physicians remotely when needed, making them crucial for preventing emergency room visits and hospital admissions.
Obstacles and Opportunities in Medicaid
Mike notes that while reimbursement is one of the easiest answers to this question, a hidden but critical issue is member churn. Members switch plans frequently, which makes it hard to track them (and their outcomes across plans). It also makes it difficult to design care pathways for them or engage in longitudinal risk arrangements on their behalf.
“It’s challenging from an economic perspective for plans and providers to see those benefits when there’s a good chance that the person will change plans, not be a part of risk arrangement moving forward, be attributed to a different primary care provider.”
It's hard to make long-term investments—providers might build trust with a member, only to have them change plans. From the plan or provider perspective, you invest significantly in engaging that member and getting them into care, but then you're unable to follow up.
Mike notes that the biggest opportunity lies in maintaining continuity for these members who both need and can benefit from it, and by extension, for providers who can better engage in long-term risk arrangements.
What’s next for Cityblock?
Cityblock is excited about publishing more content in scientific and medical journals showcasing their improvements in cost of care and inpatient reduction. They are particularly excited about findings from their advanced behavioral health program.
Read one of their most recent papers here on how a coordinated Advanced Behavioral Health CHW led program achieved statistically significant inpatient reduction.
They look forward to enhancing their product offering for integrated duals with an LTSS benefit and reducing the fragmentation that currently exists.
Finally, they are investing in AI technology to better segment members by individualizing communication for more meaningful interactions.
Interested in Cityblock? Learn more on their website and their Linkedin.
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