SHOW NOTES
GUEST INFO
Episode Guests:
Gary Clark, Senior Vice President at HUB International
https://www.hubinternational.com
Kylie Hunter, Regional Sales Manager at Berkley Accident and Health
EPISODE INTRODUCTION
Charter school leaders across the country are facing a relentless pressure that rarely makes headlines but hits the budget every single year: skyrocketing health insurance costs. On this episode of The Charter School Insider Podcast, host Daniel Casselli, President at BuyQ, sits down with two of the sharpest minds in charter school employee benefits to break down exactly what is driving these increases — and what proactive leaders can do about it.
Joining Daniel are Gary Clark, the K–12 Employee Benefits National Segment Leader at HUB International and founder of the HUB Charter segment, and Kylie Hunter, a stop loss specialist at Berkley Accident and Health who partners closely with the HUB Charter team to run a group captive purpose-built for charter schools. Together, they pull back the curtain on a complex industry — million-dollar claimants, inflation lag, fully insured versus self-funded structures, and the mechanics of a captive — and translate it into clear, actionable insight for school operators.
If your school has received a double-digit renewal notice recently, this conversation is your starting point for understanding why it happened, what your options are, and why the worst thing you can do is treat your third-largest budget line item as "set it and forget it." The data Gary and Kylie share from the HUB Charter Captive is compelling: schools participating since 2019 have seen an average of 22–26% savings relative to their previous programs — and the trend is holding.
EPISODE SUMMARY
Charter school health insurance costs are accelerating at historic rates, with medical trend inflation running at 15–16% in 2026 compared to a typical 8%, driven by a lag in post-COVID inflation working through provider contracts and a consistent 15% annual rise in million-dollar claimants. In this episode, Gary Clark of HUB International and Kylie Hunter of Berkley Accident and Health explain how self-funded health plans and group captive structures give charter schools the transparency, flexibility, and risk management tools to break out of the fully insured renewal cycle. The HUB Charter Captive, built exclusively for charter schools and leveraging their favorable demographics, has delivered average renewal increases of just 8.2% compared to 17% in the traditional stop loss market — with an estimated $7.83 million in total savings across its member schools since 2019. This episode is essential listening for any charter school CFO, COO, or executive director responsible for managing employee benefits strategy.
EPISODE TAKEAWAYS
Medical trend inflation has effectively doubled in 2026, with carriers pricing renewals at 15–16% versus the historical norm of around 8%, largely due to delayed post-COVID inflation working through provider contract negotiations.
Charter schools that move to a self-funded structure gain transparency into claims data, flexibility to design their plan, and the ability to deploy cost management tools — none of which are available under a fully insured model.
A group captive is not one-size-fits-all. The HUB Charter Captive is specifically structured around charter school demographics, which consistently outperform the general risk pool and have driven 22–26% savings for members since 2019.
Stop loss insurance is the key risk protection mechanism when going self-funded. It caps your maximum liability on both individual high-cost claimants and your total population's aggregate claims, making the financial exposure known and manageable from day one.
Organizations with fewer than 50 employees, currently high loss ratios, or a "set it and forget it" philosophy toward benefits are likely not the right fit for a captive at this time — but the right time to start exploring this is before renewal, not during it.
KEY DISCUSSION TOPICS
The current state of health insurance in 2026: why this renewal cycle is uniquely brutal and what is different about this year
The inflation lag effect: how post-COVID general inflation delayed its way into healthcare provider contracts, creating the spike employers are now absorbing
The rise of million-dollar claimants: what is driving the trend, including new high-cost specialty medications, and what it means for self-insured employers
Fully insured versus self-funded structures: the fundamental differences in control, transparency, and cost management capability
What a group captive is, how it works as an alternative risk financing structure for stop loss coverage, and why the HUB Charter Captive is structured differently than most
Real performance data from the HUB Charter Captive: 22–26% average savings, $7.83M in estimated total savings, and 8.2% average renewal increases compared to 17% in the traditional stop loss market
Common objections addressed: is self-funding too risky, what happens to employee benefits, what does the administrative lift actually look like, and who is not a good fit
WHY THIS MATTERS FOR CHARTER SCHOOL LEADERS
Health insurance is consistently a top three budget line item for charter schools, and it is growing faster than per-pupil revenue, state funding, and most other revenue streams schools have access to. For years, many schools have treated benefits renewal as an unavoidable administrative event — something that happens to them — rather than a strategic financial decision they can actively manage.
The data Gary and Kylie present makes the cost of inaction concrete. At 15–16% trend inflation compounding annually, a school's health insurance spend can double in under five years. Meanwhile, the HUB Charter Captive's member schools are averaging renewal increases of 8.2% and have collectively saved an estimated $7.83 million since 2019 by participating in a structure designed specifically for their risk profile.
The strategic implication is clear: charter school finance and operations leaders who engage proactively — understanding their claims data, evaluating self-funded structures, and building a long-term benefits strategy — are creating meaningful financial runway for their schools. Those who wait until the renewal notice arrives are leaving that runway on the table.
WHO SHOULD LISTEN TO THIS EPISODE
This episode is particularly valuable for:
Charter school CEOs, executive directors, and founders who oversee organizational budget strategy
Charter school CFOs and finance leaders responsible for managing the employee benefits line item
Charter school COOs and operations leaders who manage the benefits administration and renewal process
Charter school network leaders managing multiple campuses and seeking to standardize benefits strategy across sites
School HR directors and benefits administrators looking to better understand the tools available beyond fully insured plans
Any charter school leader who has recently received a double-digit renewal notice and wants to understand their options
NOTABLE QUOTES FROM THE EPISODE
"The state of health insurance in 2026 I would characterize as dumpster fire. These are the highest increases I've ever seen come out in a single year for employers across the board."
— Gary Clark, HUB International
"We've seen since 2019, on average, that the charter schools have achieved between 22 and 26% savings relative to the old program that they were on."
— Gary Clark, HUB International
"The frequency of million-dollar claims is on the rise. A big factor of that is these new medications that are being approved all the time. Some of the drugs you see commercials for — you have no idea that those actually are million-dollar drugs being advertised."
— Kylie Hunter, Berkley Accident and Health
"There are so many levers to pull so you can really get a hold over your risk versus just accepting that fifteen, twenty percent increase year over year."
— Kylie Hunter, Berkley Accident and Health
"If you're taking a set it and forget it approach to your third largest budget item, that's probably not wise."
— Daniel Casselli, BuyQ
EPISODE RESOURCES
How Insurance Captives Actually Work - slide deck
EPISODE FAQs
What is a group captive and how is it different from traditional stop loss insurance?
A group captive is an alternative risk financing structure in which a pool of employers — in this case, charter schools — share an additional layer of risk that they would otherwise transfer entirely to an insurance carrier. Rather than purchasing that layer of stop loss protection from a commercial insurer, the captive members collectively fund it, which gives them greater transparency, the opportunity to benefit from favorable claims performance, and more stable renewal pricing over time.
Why are charter school health insurance renewals so high in 2026?
Two primary factors are at work. First, post-COVID inflation in the general economy has taken several years to work through provider contract renegotiations, and that delayed cost increase is now hitting employer health insurance renewals. Second, million-dollar claimants are rising at approximately 15% per year, driven significantly by new high-cost specialty medications. Carriers are now pricing 2026 renewals using a 15–16% medical trend assumption, roughly double the historical norm of around 8%.
Is self-funding too risky for a charter school?
When paired with stop loss coverage, the financial risk of self-funding is clearly defined before the plan year begins. Stop loss insurance establishes a maximum liability for both individual high-cost claims and total aggregate claims across your employee population. The risk that is often overlooked is the inverse: staying on a fully insured plan exposes schools to compounding double-digit renewals with no ability to influence the outcome or understand what is driving costs.
What changes for employees if a school moves to a self-funded or captive structure?
From an employee perspective, very little changes in terms of day-to-day experience. Plan designs do not need to change, and coverage for medically necessary services remains intact by federal law. Employees may experience a network change depending on the plan configuration, and in some cases prescription copays may shift if the school moves to a different platform. The bigger change is for plan sponsors: they gain access to claims data, cost management tools, and a more strategic renewal conversation.
What size school is a good fit for the HUB Charter Captive?
Schools with at least 50 employees are generally considered candidates for self-funded structures. Below that threshold, the claims volatility risk makes self-funding difficult to manage even with stop loss protection. Beyond size, the right fit is an organization with a long-term perspective on managing health plan spend and a willingness to engage strategically at renewal time — not a "set it and forget it" approach to benefits.
CHAPTERS
00:00 Current State of Health Insurance Costs
02:45 Factors Driving Health Insurance Increases
09:05 Impact of Million Dollar Claims and New Medications
10:32 Understanding Healthcare Cost Increases
14:20 Exploring Self-Funded vs Fully Insured Plans
16:55 The Benefits of Self-Funding
21:05 Introducing the Hub Charter Captive
26:45 Evaluating the Performance of Captives
28:00 Addressing Common Misconceptions
35:05 Identifying the Right Fit for Self-Funding
ABOUT OUR HOST
Daniel Casselli is a life-long learner whose passion for education has driven his professional endeavors. He is a former classroom teacher and youth ministry director whose entrepreneurial spirit landed him in the world of education technology. At EVERFI Inc., Daniel helped run the business development efforts for EVERFI’s Financial Education Program and the company was eventually sold to Blackbaud for $750M in 2021. Shortly before EVERFI’s acquisition, Daniel joined Class Technologies as one of the earliest sales hires and went on to lead K12 Enterprise Sales and helped the company land its first 100+ K12 customers across public, charter, and private schools. Daniel brings his unique experiences to BuyQ where he is focused on growth, operational excellence, business strategy, and client satisfaction. He is a graduate of Grove City College where he studied Religion and History.
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