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Episode #11 - Responsible financial management with Raj Thakkar, Founder & CEO of Charter School Business Management
SHOW NOTES
3 min read
SHOW NOTES
GUEST INFO
Episode Guest:
Dermoth Mattison, Founder & Executive Director of South Shore Charter School
Connect with Dermoth on LinkedIn
Website:
https://www.southshorecharterschool.org/
EPISODE SUMMARY
What does it really take to build a charter school from scratch—and do it well?
In this milestone 50th episode, we sit down with Dermoth Mattison, founder of South Shore Charter School, to explore how intentionality in the early days can lay the groundwork for a thriving school culture and academic excellence. From rigorous SUNY authorizer expectations to community-driven design, Dermoth walks us through the highs and hurdles of opening a school that serves both heart and head.
Discover how systems and culture are inseparable, how South Shore hit a 99% student success rate in its first year, and why your Plan B (and C) might be the key to unlocking long-term success.
If you're a school leader, executive, or founder planning your next move—this is the episode you didn’t know you needed.
EPISODE TAKEAWAYS
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Start Strong, Stay Strong: Systematize from Day 1. Codifying systems early protects instructional time and builds teacher confidence.
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Culture is Built, Not Hoped For: Systems that reflect core values are essential for developing a school identity students and staff can believe in.
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The “Big 3” for Teacher Support: Weekly lesson plan feedback, classroom observations, and 1:1 coaching are non-negotiables at South Shore.
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Plan for the Unexpected: A delayed opening turned into a year of strategic preparation that led to measurable student success.
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Document Everything: From Google Drive to huddles and PDs, building and reinforcing system knowledge is key for scale.
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Lead with Community, Not Assumptions: Dermoth’s grassroots approach ensured that South Shore was built with families, not for them.
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Adapt Quickly, Listen Deeply: When systems break (like their initial dismissal routine), open feedback loops and quick iteration made all the difference
RESOURCES
Book: Leverage Leadership by Paul Bambrick-Santoyo
CHAPTERS
00:00 Introduction to Dermoth's Journey
02:01 Founding South Shore Charter School
04:56 Navigating the SUNY Charter Process
07:42 Building Early Systems and Culture
10:50 Establishing Sustainable Systems
13:29 Operational Systems and Teacher Support
16:24 Feedback Loops and System Refinement
17:42 The Interplay of Culture and Systems
19:36 Challenges in School Culture
22:39 Resources for School Leaders
ABOUT OUR GUEST
Dermoth Mattison is the Founder and Executive Director of South Shore Charter School, a nationally recognized public charter school serving communities across Long Island, New York. With nearly 20 years of experience in charter school leadership, he is a lifelong advocate for educational equity and opportunity.
Mr. Mattison has led schools that consistently outperform local districts and close achievement gaps for underserved students. During the 2023–24 school year, 99 percent of scholars at South Shore met growth goals in reading and math on the NWEA MAP assessment. In 2024–25, the school ranked in the 94th percentile in reading and 88th percentile in math nationally on the same assessment, reflecting both exceptional growth and high achievement. Before founding South Shore, he served as a principal where his school consistently outperformed the local district and was recognized for strong student growth and academic achievement.
He founded South Shore and developed its full academic and cultural model from the ground up. He led the charter development process and engaged families, educators, and community leaders to ensure the school reflected local needs and aspirations. A strategic leader, he builds high-capacity teams, coaches emerging leaders, and designs systems that align vision with daily execution. His leadership is grounded in the school’s core values: Integrity, Grit, Resilience, Excellence, Accountability, and Tenacity. These values form the belief that every scholar and staff member can proudly say, “I am GREAT.”
Mr. Mattison oversees the school’s operations and finances, ensuring strong systems, sound stewardship, and clean financial audits since inception. He holds New York State certifications in teaching and school leadership and is currently pursuing a doctoral degree in Educational Leadership. He is a proud husband and father of three wonderful children.
Mr. Mattison is committed to expanding access to high-quality public charter schools in high-needs communities across Long Island, New York.
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...
