Building a pipeline to success
Leonard Webb is a former law enforcement professional turned educator. He is an international speaker, coach, and visionary that is dedicated to transforming lives and systems through purpose driven leadership, activism, and unapologetic authenticity. Born and raised in New York, Leonard’s journey from the correctional system where he served incarcerated men and supported their turnaround from prison to productive citizen. He now leads efforts to empower the next generation of change makers and end the school to prison pipeline. With lived experiences and academic insight, he bridges the gap between administration, teachers, parents, and students to build a pipeline to success and improve educational outcomes. He believes students do not need permission for greatness; they just need direction.
As the founder of Webbolutionary Motivation, LLC, Leonard supports students, schools, youth organizations to improve and reimagine leadership while centering student voice. As a thought leader in college and career readiness, he demonstrates passion and joy while providing strategy in the work of growth and development.
He has spent the last 7 years working with schools, universities, and companies across the country, sharing his dynamic message about discipline, decision making, adaptability and being accountable. His work within the criminal justice system and schools led to him being appointed by Governor Hogan (Md.) to the Juvenile Justice School Board for the State of Maryland and he was the recipient of the NAACP of Allegany County, Educator of the Year Award 2024.
Leonard has provided professional development and delivered keynotes all across the United States and Australia. He highlights the pressing need for addressing issues of school discipline, chronic absenteeism, and improving academic success. In the spirit of “see a problem, create a solution”, he supports student’s in identifying purpose and finding directions that dramatically reduces expulsions, suspensions, dropouts, and school avoidance. He provides coaching and strategies to young people to break this cycle of incarceration and focuses on academic success and resilience. He consults and trains educators with strategies to help them connect with students, focus on student’s strengths, and provide the support that improves behavior rather than relying on discipline.
Who We Have Served
Testimonials
Heidi Laupert
Principal, Allegany High School
We will continue to use Leonard Webb as a speaker for our professional development as we continue to confront our implicit biases. He is a breath of fresh air.
Vicki Leasure
BGCA Program Coordinator, Salvation Army
Leonard gave the 3rd to 5th graders advice that I wish someone would have given me when I was their age. Everyone needs a Leonard on their side. He cares, He listens, and he is real.
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