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Organizational Development | Executive Coaching | School and Instructional Improvement
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“On a mission to
Increase educational impact and outcomes”
Dr. Cheryl Proctor
Chief Executive Officer & Owner
Keynote Speaking | Coaching & Consulting Strategic Planning | Leadership Development
Dr. Cheryl Proctor
ABOUT
FOUNDER AND CEO
Dr. Proctor is a seasoned educational leader whose blend of organizational insights and instructional innovation produces results. After decades of experience in school districts across the nation, her career is marked by transformation from the classroom to the boardroom. Most notably, she has:
Served nearly 500,000 students across three school districts
Exited 15 schools from the State Comprehensive Support and Improvement (CSI) / Targeted Support and Improvement (TSI) identification for increased academic achievement during 2022-2024 school years
Made a double digit increase over state averages in English Language Arts (ELA) and Math proficiency for grades 3-8 during 2022-2023 school years
Increased the 4-year and 5-year graduation rate for the 2021-2022 school year (PPS)
Launched bond campaigns resulting in 6 modernized school campuses during the 2022-2024 school years
Supervised principals for 12 comprehensive high schools and career and technical high schools during the 2018-2021 school years
Decreased the number of state accountability system identified schools from 106 state identified schools in 2016 to 63 in 2018 by leading district staff in the development of state approved School Improvement Plans (SIP).
Facilitated 57% improvement on the District School Progress Report (SPR) during the 2017-2019 school years
WATCH: LEARN MORE ABOUT INSIGHTS ON LEARNING
CORE VALUES
Insights on Learning’s core values are integral to its process and product.
Access: Education promises that all students become equipped with the tools for intellectual and social mobility. For us, all means all–even if that means we must differentiate our approach to meet the individual needs of students.
Care: The only constant in life is change. As the education system evolves, we must re-examine our assumptions and reimagine new ways of working. Since teams are our most valuable commodity, care commands that we design learning experiences and professional opportunities that align with organizational needs while tending to the people side of change.
Excellence: All students can learn. Therefore, we support teams to set high expectations and innovate new approaches when business as usual falls short.
Growth: We rely on research-based best practices and data driven insights to shift outcomes for students and educators. We are not satisfied with the status quo.
STRATREGIC CONSULTANT. LEADERSHIP & DEVELOPMENT COACH.
Keynote Speaker
Through her executive education consulting, Insights on Learning, Dr. Proctor uses her extensive knowledge, wide-ranging experience, and proven leadership in K -12 education to increase overall student performance and narrow achievement gaps by creating the conditions for a high-quality education for all children. Through targeted universalism, she centers equity and inclusion by partnering with parents, families, teachers, volunteers, and community members to seek student-focused outcomes. “Our clients are impressed with our methods, proven systems, and passion for urban education. We view our students individually for the assets they bring to the learning experience. From this lens, we are able to provide a personalized approach to instruction that focuses on meeting student needs while bridging gaps that would otherwise prevent our most marginalized students from being successful,” explains Dr. Proctor.
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INSIGHTS ON LEARNING ALIGNS RESOURCES THAT CLOSE THE ACHIEVEMENT GAP...
a greater impact for all while raising the bar of what is possible when we invest in members of the next generation. Insights on Learning offers education consulting to partner districts through strategic planning, coaching and consulting, leadership development, and keynote speaking.
EDUCATIONAL LEADERS FIND IT VALUABLE TO CONTRACT WITH INSIGHTS ON LEARNING...
to support and build effective systems rooted in continuous improvements that yield greater impact for all students, especially those most marginalized. Our services include leadership/staff development, consulting, and coaching to build stronger systems, strategic planning as well as keynote speaking that raises awareness. For more information on Dr. Cheryl A Proctor or her company, Insights on Learning, search Insights on Learning on Instagram, Facebook, LinkedIn, and Twitter
SERVICES
Our services encompass all levels of system building from the individual to the institutional. We support educational organizations to enhance operational structures, foster team collaboration, and build leadership capacity to create more effective learning environments.
ORGANIZATIONAL DEVELOPMENT
Align organizational practices to strategic priorities using Insights on Learning’s organizational transformation approach.
EXECUTIVE COACHING
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We provide personalized coaching and professional development for education executive leaders, equipping them with the skills needed to foster positive change, strengthen system practices, and cultivate thriving organizational culture.
SCHOOL AND INSTRUCTIONAL IMPROVEMENT
Strengthen leadership, teaching practices and school operations using Insights on Learning’s organizational transformation approach.
SERVICES
Services
DIVERSITY, EQUITY & INCLUSION
Design & Support
ORGANIZATION DEVELOPMENT
Keynote
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EXECUTIVE LEADERSHIP
Coaching
Our Associates
Dr. Sabriya K. Jubilee
Dr. Sabriya K. Jubilee is an accomplished educational leader specializing in diversity, equity, inclusion, and social justice. With extensive experience guiding organizations toward equitable practices, she has held multiple leadership roles focused on dismantling systemic inequities and creating transformative educational environments.
Dr. Jubilee is known for her visionary approach to equity, setting strategic direction, and designing organizational structures that promote inclusive outcomes. Her commitment extends to fostering meaningful systemic changes, advocating for social justice, and supporting educational innovation and reform.
A recognized speaker, published author, and educator, Dr. Jubilee holds credentials in professional coaching and teaches interdisciplinary courses in Urban Education, Sociology, Psychology, and Human Services. She has participated in esteemed fellowships and leadership programs aimed at advancing equity-focused educational practices.
Dr. Jubilee holds multiple advanced degrees in education and related fields, reflecting her deep expertise in urban education, leadership, and African American studies. Beyond her professional work, she actively contributes to her community through civic engagement and spiritual leadership roles.
Lisette Powell
Lissette Powell is a visionary educator and leader with over three decades of experience in advancing educational innovation and transforming school systems at local, national, and international levels. Her extensive career encompasses diverse roles in both public education and private sectors, characterized by strategic leadership, classroom expertise, and global engagement.
Powell’s early professional contributions include instructional excellence in foundational education, curriculum design, and pioneering initiatives to engage families in the educational journey. Her enduring advocacy for early childhood education underscores her belief in developing core academic competencies and essential life skills critical for sustained academic achievement.
In the realm of educational technology, Powell has held influential positions focused on leveraging data-driven strategies and evidence-based approaches to foster measurable improvements in student learning outcomes. Her expertise in coaching, professional development, and system-wide implementation has successfully guided transformative efforts across multiple regions, including significant projects in the United States, the Caribbean, the Middle East, and Latin America.
Driven by collaboration and committed to impactful change, Powell continues to lead initiatives aimed at empowering educational communities, enhancing instructional effectiveness, and establishing supportive environments that promote success for educators and students alike.
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