Educator Profile    Educators

Ryan Sykes (VA '19)


Pleasants Lane Elementary School
Petersburg, VA

At the time of the Award, Ryan Sykes was:

Assistant Principal
Carter G. Woodson Middle School
Hopewell, VA

Grade(s): 6, 7, 8

Biographical Information

If you’re looking for Ryan Sykes, Principal at Pleasants Lane Elementary School  in Petersburg, Virginia, skip his office. You’ll likely find him high-fiving and fist-bumping students and teachers in the halls, or modeling lessons and positive behavior supports in classrooms. Sykes has a magical ability to connect with students. He knows every student by name and builds relationships with all of them, especially those with the greatest needs. His energy is boundless and contagious. Sykes is the first one on the dance floor at school socials, eats lunch with students in the cafeteria and tackles the obstacle course with them on field day, coaxing reluctant students from the sidelines into the action. He spent an entire day clad in the leotard and tights of Frozone, a character from “The Incredibles,” to fulfill a promise after students reached their target on state assessments.  Sykes serves on the district’s action team for improving attendance, studying specific student data as he works with attendance officers to problem-solve with families. His background in special education makes him particularly sensitive to working with all people’s talents and challenges.

Smart, confident and respected, Sykes goes the extra mile to get the best from students, teachers and parents. He researched, coordinated and implemented an advisory program that helps students foster peer-to-peer relationships through positive behavior, communication, social and empathy skills. Sykes supervised a yearlong STEM program for underserved African American young men at Woodson made available through a grant from Virginia State University and Verizon. Students move to high school brimming with confidence because of the advisory groups, mentoring sessions and tutoring services he facilitates.

Sykes earned a bachelor’s in interdisciplinary studies in 2011 and a master’s in administration and supervision in 2014 from Virginia State University. He is pursuing a doctorate in administration and supervision.

Press release: Being a Superhero for Students Earns Assistant Principal Ryan Sykes a $25,000 Milken Educator Award

VIDEO: Virginia First Lady Pamela Northam's remarks before Ryan's Milken Award surprise

VIDEO: Ryan Sykes shares some thoughts at his surprise Milken Award assembly

VIDEO: Ryan Sykes talks with the Milken Family Foundation after the assembly


Related Connections

Article: Milken Educators Take Learning to the Next Level at 2021 NIET National Conference

Article: Why I Became a Teacher

Article: Spotlight: Ryan Sykes (VA '19)

Educator Quote:

"I hope my students recognize that I really care about them..." (read more)

Ryan Sykes In The News

Hopewell Assistant Principal Receives $25,000 Educator Award
WWBT-TV  |  NBC  |  Nov 06, 2019  |  Richmond, VA

WATCH --> Hopewell Teacher Surprised with $25K Award: ‘I Couldn’t Believe it’
WRIC-TV  |  ABC  |  Nov 06, 2019  |  Richmond, VA

Hopewell Educator Receives Prestigious Milken Educator Award
The Progress-Index  |  Nov 06, 2019  |  Petersburg, VA

Hopewell Assistant Principal Wins $25,000 Award Recognizing Excellence in Education
Richmond Times-Disptach  |  Nov 06, 2019  |  Richmond, VA

Hopewell Assistant Principal Surprised with $25k Teaching Award
WTVR-TV  |  CBS  |  Nov 06, 2019  |  Richmond, VA