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45: The Long Game of Leadership
In this episode of the CheckBox Pro Series, Missy sits down with Rosalind DaCruz, Founder and Executive Director of RISE Prep Academies. Rosalind shares her journey from Teach For America corps member and high school history teacher to founding a charter school just three years into her teaching career—and what it's been like to lead and grow that organization for nearly a decade.
Rosalind reflects on the evolution of her role from Founding Head of School to Executive Director, naming the often-unspoken challenges of scaling a school network: letting go of daily classroom life, resisting the urge to solve every problem personally, and learning to trust others with work she once owned. She speaks candidly about the emotional weight of this transition, especially as RISE Prep expands from a single kindergarten class into a K–12 network serving up to 1,400 students, with multiple campuses and major facilities projects underway.
The conversation also explores how Rosalind sustains herself through this demanding season of leadership. As a working parent and long-time school founder, she shares the practical systems that help her stay grounded—including a weekly closeout and look-ahead routine that brings clarity, accountability, and grace to both her professional and personal life. This episode is an honest, encouraging listen for school leaders navigating growth, transition, and longevity in the work.
Key Takeaways:
- What it really feels like to transition from founder to Executive Director as schools scale.
- Why stepping back from day-to-day school life can be both painful and necessary.
- How executive coaching and time audits supported Rosalind's leadership shift.
- The role of grit, strategic pivots, and persistence in sustaining a growing charter network.
- A simple weekly planning practice that supports leadership, parenting, and well-being.
Connect with Roz:
- Learn more about RISE Prep Academies: https://www.riseprep.org
- Connect with Rosalind DaCruz on LinkedIn https://www.linkedin.com/in/rosalind-dacruz-3a3a4177/
About CheckBox Pro: CheckBox Pro helps school leaders create sustainability through added capacity—taking repetitive tasks off their plates so they can focus on what matters most. https://www.checkboxpro.com/
Licensed music ID: ILRNI9DIEHE4JTVQ Music: Energizer by Chris Phaze licensed through Premium Beat by Shutterstock ID: ILRNI9DIEHE4JTVQ
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By Missy CouchIn this episode of the CheckBox Pro Series, Missy sits down with Rosalind DaCruz, Founder and Executive Director of RISE Prep Academies. Rosalind shares her journey from Teach For America corps member and high school history teacher to founding a charter school just three years into her teaching career—and what it's been like to lead and grow that organization for nearly a decade.
Rosalind reflects on the evolution of her role from Founding Head of School to Executive Director, naming the often-unspoken challenges of scaling a school network: letting go of daily classroom life, resisting the urge to solve every problem personally, and learning to trust others with work she once owned. She speaks candidly about the emotional weight of this transition, especially as RISE Prep expands from a single kindergarten class into a K–12 network serving up to 1,400 students, with multiple campuses and major facilities projects underway.
The conversation also explores how Rosalind sustains herself through this demanding season of leadership. As a working parent and long-time school founder, she shares the practical systems that help her stay grounded—including a weekly closeout and look-ahead routine that brings clarity, accountability, and grace to both her professional and personal life. This episode is an honest, encouraging listen for school leaders navigating growth, transition, and longevity in the work.
Key Takeaways:
- What it really feels like to transition from founder to Executive Director as schools scale.
- Why stepping back from day-to-day school life can be both painful and necessary.
- How executive coaching and time audits supported Rosalind's leadership shift.
- The role of grit, strategic pivots, and persistence in sustaining a growing charter network.
- A simple weekly planning practice that supports leadership, parenting, and well-being.
Connect with Roz:
- Learn more about RISE Prep Academies: https://www.riseprep.org
- Connect with Rosalind DaCruz on LinkedIn https://www.linkedin.com/in/rosalind-dacruz-3a3a4177/
About CheckBox Pro: CheckBox Pro helps school leaders create sustainability through added capacity—taking repetitive tasks off their plates so they can focus on what matters most. https://www.checkboxpro.com/
Licensed music ID: ILRNI9DIEHE4JTVQ Music: Energizer by Chris Phaze licensed through Premium Beat by Shutterstock ID: ILRNI9DIEHE4JTVQ