Health insurance renewals are shaping up to be one of the biggest financial stressors charter schools will face heading into 2026. In this episode, Daniel sits down with Gary Clark, Senior VP at HUB International and head of HUB’s national charter school health practice, to break down why this renewal cycle is projected to be the most challenging in decades—and what school executives can do right now to protect their budgets.

Gary explains the macro forces driving unprecedented premium increases: delayed inflationary impact on provider contracts, rising hospital and pharmacy costs, and a surge in million-dollar claims nationwide. He also reveals surprising insights specific to charter schools, particularly high maternity costs and rising mental health utilization.

The conversation demystifies health plan structures (fully-insured, level-funded, self-funded, and captives) and shows why choosing the right structure can unlock control, flexibility, and meaningful cost savings. Gary also shares real-world examples of charter networks that reduced costs, built reserves, and improved employee benefits through strategic plan design.

Whether you’re a CEO, CFO, HR leader, or board member, this episode gives you actionable steps to prepare for 2026, avoid budget shocks, and approach health insurance as a strategic advantage, not a liability.

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Master scheduling isn’t just a logistical task—it’s a strategic lever that shapes student outcomes, staff experience, and long-term sustainability. In this episode, Daniel sits down with Matt Troha, former COO of Mastery Charter Schools and now Partnerships Manager at Timely, to unpack why the master schedule is often the most dreaded project of the year—and how AI, data-driven models, and smarter operational design are changing everything.

With 20 years of K–12 experience, Matt walks listeners through:

-How strategic priorities must inform the instructional model.

-Why accurate enrollment projections determine financial health.

-How adult-centric constraints can unintentionally weaken student schedules.

-What zero-based scheduling can do for efficiency.

-Why traditional tools (Excel, sticky notes, whiteboards) can’t keep up.

-And how AI-powered scheduling is saving schools weeks, not days.

Charter executives will walk away with a deeper understanding of how to align mission, budget, and instruction; using a schedule as a strategic asset rather than a burden.

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Facilities planning isn’t just a real estate decision — it’s a strategic leadership moment that shapes a school’s long-term viability, culture, and stability.

In this episode, Daniel sits down with John Sun, CEO of Blueprint (formerly Pacific Charter School Development) — a nonprofit facility solutions partner that has supported charter schools for over 20 years. John brings deep experience in helping charter leaders navigate financing, real estate development, and the decision-making required to secure sustainable school homes.

From incubating in shared spaces to sequencing financing across growth stages, John outlines a clear, grounded framework for leaders who want to move from “dream building” to viable facility strategy — without losing sight of mission, culture, or financial health.

Whether you're in year zero planning mode, thinking about scale, or facing tough space constraints, this episode will give you clarity, confidence, and next steps.

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What happens when your mission requires more staff, but your budget says less spending?

In this insightful episode of The Charter School Insider Podcast, host Daniel Casselli sits down with Richard Royal, Executive Director of Denver Language School (DLS) — a top-performing K–8 immersion charter in Colorado — to explore how to build a sustainable staffing and budgeting model from first principles.

Richard shares how DLS achieves exceptional outcomes in both Mandarin and Spanish immersion programs while facing lower per-pupil funding than district peers. He walks us through his strategic shift in staff compensation, the challenges of realigning pay scales, and the importance of leading with transparency and mission alignment.

From tough board conversations to courageous leadership decisions, this episode is a masterclass in strategic budgeting for charter school executives — balancing people, purpose, and performance.

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Strong authorizer relationships are the foundation of long-term charter school success — but they can also be one of the most misunderstood.

In this episode of The Charter School Insider Podcast, host Daniel Casselli sits down with Kathryn Connell-Espinosa, Executive Director of the SUNY Charter Schools Institute, to discuss what effective collaboration between schools and authorizers really looks like.

Kathryn shares more than a decade of insight from overseeing 237 charter schools across New York, offering a rare glimpse into what makes great authorizer-school partnerships thrive. She explains how open communication, strong governance, and early transparency can help schools avoid pitfalls — and why authorizers are most successful when the schools they serve succeed.

Whether you’re a school leader, board chair, or new founder, this episode will help you build stronger, more productive relationships with your authorizer — and understand the key role they play in your school’s accountability, growth, and long-term success.

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On Episode #59 of The Charter School Insider Podcast, host Daniel Casselli sits down with Missy Couch, Founder & CEO of Checkbox Pro LLC, to discuss one of the most pressing challenges in charter school leadership: time.

Missy shares how Checkbox Pro helps school leaders reclaim their schedules, avoid burnout, and refocus on the work that truly moves their schools forward. From practical tips on delegation and boundaries to maximizing technology without letting it take over your life, this episode is packed with strategies to help executives lead effectively and sustainably.

Whether you're a founding school leader juggling it all or part of a growing network managing multiple campuses, this episode will show you what’s possible when you gain back control of your time—and your sanity.

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Enrollment isn’t just about filling seats—it’s about building a culture where every staff member understands their role in sustaining and growing a school community.

In this episode of The Charter School Insider Podcast, host Daniel Casselli sits down with Yoni Samuel-Siegel, Chief Operating Officer at Prospect Schools in Brooklyn, NY. With 25 years in education, Yoni shares how Prospect shifted from relying on word-of-mouth enrollment to building a structured, data-informed culture of recruitment and retention.

From creating seamless family experiences to introducing CRMs like HubSpot, Yoni unpacks how Prospect Schools aligned operations, leadership, and community to achieve double-digit enrollment growth. If you’re a charter school executive wondering how to transform your enrollment strategy into a network-wide movement, this episode is for you.

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In this episode of The Charter School Insider Podcast, host Daniel Casselli, President of BuyQ, sits down with SarahGennie Colazio, Director of Finance & HR at Windsor Charter Academy.

What happens when a charter school dares to rethink one of its biggest expenses—employee health insurance? For Windsor Charter Academy, the answer was staggering: $1.4 million in savings over six years.

SarahGennie shares how her school shifted from a traditional fully insured model to a self-funded captive insurance plan, unlocking cost savings while enhancing employee benefits. From IVF coverage and hearing aids to mental health support and retention bonuses, Windsor turned financial savings into a stronger culture of care.

This episode is a case study in financial strategy, employee retention, and innovation—perfect for school leaders looking to stretch every dollar while supporting their teams.

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Is your charter school board stuck in operational weeds instead of leading with vision? In this episode of The Charter School Insider Podcast, host Daniel Casselli speaks with Carrie Irvin of Bellwether and John Troy of WorkTogether, two national experts in board development and executive leadership.

Together, they explore how charter school executives can revitalize underperforming boards, build stronger governance cultures, and create true strategic partnerships between leadership and the board.

You’ll learn how to shift your board’s focus from micromanagement to mission-driven leadership, why curiosity and trust are essential for board engagement, and how to address dysfunction using tools like board retreats, coaching, and honest conversations.

If you're navigating a stagnant board, facing board turnover, or stepping into a new leadership role, this episode offers clear takeaways and expert guidance to help you get your board unstuck—and unlock your school’s full potential.

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In Episode 55 of The Charter School Insider Podcast, host Daniel Casselli sits down with Dr. Richard Seigler-Carter, Managing Director of the LeveragED Foundation, to unpack a powerful truth: schools don’t thrive on curriculum alone—they thrive on people.

Dr. Seigler-Carter shares his journey from dance teacher to principal to leading 14 high-performing schools, and now shaping leadership development nationwide. Together, they tackle one of the most overlooked elements of school success—people and performance management—and why investing in leaders is the ultimate investment in students.

This conversation explores how charter school executives can create a culture of feedback, differentiate leadership for diverse teams, and implement business-inspired management systems that still honor the relational nature of education.

If you’re a school leader wondering how to better develop your people while managing systems and performance without losing your soul—or your staff—this episode is your roadmap.

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