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Episode #26 - What’s missing in your enrollment strategy with Vanessa Segovia Barry, Founder of Mariposa Consulting Group
SHOW NOTES
3 min read
SHOW NOTES
GUEST INFO
Episode Guest:
Michael Wimbish, Chief Financial Officer at Aspire Public Schools
Website:
https://aspirepublicschools.org/
EPISODE SUMMARY
Charter school finance leaders are navigating one of the most complex operating environments the sector has faced in years. From declining enrollment and shifting funding models to increasing compliance requirements, CFOs must balance financial sustainability while staying true to their mission.
In this episode of The Charter School Insider Podcast, host Daniel Casselli, President at BuyQ, sits down with Michael Wimbish, Chief Financial Officer at Aspire Public Schools, to discuss how finance leaders can lead through uncertainty while building trust across their organizations.
Managing finances for 36 charter schools across California, Michael shares how Aspire approaches financial sustainability, transparent communication, and data-driven decision making. He also introduces a practical framework that helps leaders think about the biggest financial pressures facing charter school networks today.
For charter school executives navigating today's uncertain landscape, this episode offers valuable insights into how CFOs can balance mission, metrics, and organizational trust.
EPISODE TAKEAWAYS
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Charter school CFOs must lead through growing financial uncertainty - Declining enrollment, increased oversight, and shifting funding streams are creating new financial pressures across the sector.
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Financial frameworks help simplify complex decisions - The 3Es + One-Time Funding framework provides a practical way to evaluate financial sustainability.
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Transparency strengthens trust across school networks - Clear and open communication about financial realities helps staff understand difficult decisions.
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One-time funding should be used for strategic, temporary investments - Avoid building permanent commitments with temporary funding sources.
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Data-driven enrollment planning is critical - Charter networks must analyze historical enrollment trends and demographic shifts to plan sustainably.
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Financial leadership is both analytical and relational - Effective CFOs must balance metrics with mission-driven decision-making and strong communication.
WHY THIS MATTERS FOR CHARTER SCHOOL LEADERS
Charter school leaders today must navigate a rapidly evolving financial landscape while maintaining strong academic outcomes.
As funding pressures grow and enrollment patterns shift, leaders must develop systems that support both financial sustainability and school-level autonomy.
This episode offers practical insights for charter school executives, CFOs, and operations leaders on how to:
- Build financial frameworks for long-term sustainability
- Communicate financial realities across large organizations
- Use data to forecast enrollment and budget planning
- Balance mission-driven investments with financial discipline
For charter networks operating multiple schools, these strategies are essential for leading through uncertainty while maintaining trust and alignment across teams.
EPISODE RESOURCES
Financial decision-tree models used in charter networks
The 3 E’s and one O for charter school budgeting
CHAPTERS
00:00 Introduction to Michael Wimbish and Aspire Public Schools
01:41 Current Environment in Charter School Finance
04:35 Framework for Financial Sustainability
07:37 Decision-Making and Communication in Finance
10:22 Metrics for Financial Health
13:24 Balancing Mission and Financial Sustainability
16:13 One-Time Funding vs. Long-Term Investments
16:38 Strategic Financial Planning and Compensation Alignment
20:20 Effective Communication in Financial Management
26:28 Data-Driven Enrollment Strategies
29:45 Leveraging Resources and Networks for Financial Leadership
32:54 The Importance of Transparency in Leadership
ABOUT OUR GUEST
Michael Wimbish has served as Aspire’s Chief Financial Officer since 2021. In this role, Michael leads Finance, Accounting/AP, Payroll, Financial Compliance, and Real Estate for Aspire’s 36 schools, which serve over 15,500 scholars in grades TK-12 across the State of California.
Michael previously served as the Director of Finance at Aspire for 2.5 years, leading and developing Aspire’s Finance team and managing budgeting, forecasting, and financial reporting processes across Aspire. Before joining Aspire Public Schools, Michael spent 8 years at Intel Corporation and 4 years at The Clorox Corporation in various Finance roles. One of his passions is working with young people as a basketball coach. The opportunity to combine his passions for finance and serving young people inspired him to join the Aspire team. Michael is a proud alumni of the University of Southern California, where he earned a B.S. in Business Administration, with an emphasis in Corporate Finance. In 2024, Michael completed the FOX Fellowship for charter management CFOs and COOs.
Outside work, Michael enjoys spending time with his wife Jesslynn, their five daughters: Kailynn, Jordynn, Kendall, Mikayla, and Makenzie, and one son, Dominick.
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.
You can listen to Charter School Insider: Lessons from the Nation's Top Charter School Operators on your favorite podcasting platform...
