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Administrative Team Profiles

Dr. Brian Fellows enters his first year of Principal at Deep Run High School and has twenty-two years of educational experience with 2019-2020 being his nineteenth year as an administrator. In 2010, he was named a Principal of Distinction by the Commonwealth of Virginia. Dr. Fellows is a proud product of HCPS and is a 1994 graduate of Mills E. Godwin High School. He holds an undergraduate degree in Mathematics from Emory and Henry College. He also earned his Master’s degree in Administration and Supervision and his Doctor of Philosophy degree in Educational Leadership from Virginia Commonwealth University. Education is a passion and is very important to the Fellows Family. He and his wife, Carey, who is the Associate Principal at Harold Macon Ratcliffe Elementary School in Henrico, have two children who attend Henrico County Public Schools. His sister, Dr. Meredith Parker, is the Director of Human Resources for Powhatan County Public Schools. His mother was a teacher and his father worked for over forty years in Richmond City Public Schools serving as the Principal of Albert H. Hill Middle School from 1990-2014. Brian has been a teacher at Tuckahoe Middle, an Assistant Principal at Godwin High, the Principal at Tuckahoe Middle and was the first Principal in the history of Holman Middle (from 2009-2019). Brian also has an unhealthy obsession with the Philadelphia Eagles. #FlyEaglesFly


Mrs. Cheryl Montgomery is thrilled to be serving her second year as Deep Run’s Associate Principal.  She has 28 years of educational experience with this being her fifteenth year in administration.  Mrs. Montgomery worked as a coach and teacher at Henrico High School, teacher, administrative aide, science department leader, assistant principal and associate principal at Hermitage High School.  Mrs. Montgomery holds a Bachelor’s Degree in Biology Education from Virginia Commonwealth University and is also certified to teach, General Science, Earth, and Space Science and Chemistry.  She also holds a Master’s Degree in Administration and Supervision from Virginia Commonwealth University.



Mr. Michael Fennessey is starting his 7th year here at Deep Run High School.  Prior to becoming an Assistant Principal at Deep Run, Mr. Fennessey served as an Administrator at James River High School for seven years. He began his teaching career at Providence Middle School in Chesterfield County where he taught mathematics.  After teaching five years at the middle school level he taught at Chesterfield Community High School. He holds a Bachelor of Science in Mathematics from the State University of New York at Cortland, and a Master of Administration and Supervision from the University of Phoenix.  Mr. Fennessey resides in Hanover County with his wife and two high school-aged children.  He enjoys playing soccer, riding his bike and spending time with family and friends.  Growing up in New York, he still roots for the Giants, Mets, Knicks and the Rangers. His passion is working with students and building lasting relationships to help each student see success.  He is very proud to be working with the Mentor Program and intermural sports during lunch.     


Mrs. Hope W. Parham began her career in education in 2000 at Godwin High School as a chemistry teacher.  During her time there she taught all levels including honors and advanced placement. She served as a class and club sponsor, mentor to young teachers, and an administrative aide.  In 2015, Mrs. Parham was promoted to Assistant Principal at Deep Run High School.  She has earned her Bachelors’s in Chemistry from the University of Virginia and a Master’s degree in Educational Leadership from Regent University.  She is a native Richmonder and in her spare time enjoys music and working with philanthropic efforts to support students in need. She is a wife and mother of three children.



Ms. Laura McKinney is beginning her third year at Deep Run High School and began her teaching career in Apex, NC.  After earning a BA in English at Virginia Tech and entering the workforce, she realized that she wanted a career where she could have an impact.  Returning to earn her teaching license at the University of NC- Greensboro, she moved to Cary, NC, where she began teaching English at Apex High School for six years.  After relocating to the Richmond area, she began teaching English at Freeman High School and earned her Masters Degree from VCU. In 2006, Ms. McKinney became the Coordinator for Assessment and Remediation at Freeman High School and served in that role until 2017.  As the CAR, she learned the value of building relationships with colleagues, worked with many individuals throughout Henrico county, and strived to impact student lives. In 2017, she became an Assistant Principal at Deep Run and enjoys the community, the teachers, and staff members. Ms. McKinney has lived in Henrico for the longest period of her life having moved around from Connecticut, New York, and then Portsmouth and Virginia Beach.  She went to First Colonial High School.  Currently, her two children are products of the Henrico County Public Schools with a daughter in middle school and a graduated senior who will continue the Hokie family tradition by attending Virginia Tech.


Ms. Shelly Brown is the principal’s secretary.


Mrs. Catherine Caldas is currently in her seventeenth year of teaching for Henrico County Public Schools.  She began teaching at Hermitage High School.  Mrs. Caldas is currently serving as an exceptional education teacher and one of Deep Run’s Administrative Aides.  She graduated from Godwin High School, obtained her undergraduate degree and Master’s degree in Educational Leadership from Virginia Commonwealth University.  Mrs. Caldas enjoys spending time with her husband, two daughters, and the family dog at the beach.





Mr. Dan Dickey is in his 17th year in education, and his 9th year at Deep Run. Dan earned his Bachelor of Arts in Education, with a concentration in Social Studies from the University of Akron, and his M.Ed. in Educational Leadership from James Madison University. Before coming to Deep Run, Dan served as a teacher, and later Director of Student Activities at Caroline High School in Milford, VA. Dan currently teaches AP US History and World History II at Deep Run. Dan also serves as an Administrative Aide, where he assists the administrative team in areas of attendance, transportation, safety and security, discipline, the mentoring program, graduation, and many other areas. One of his goals as an administrative Aide is to provide support for the students of Deep Run so they can be successful. Dan is married to his wife of 13 years, Amanda, and they have two children, Michael age 10 and William age 8. Dan enjoys fishing, camping, canoeing, golf, running, playing cards, and especially spending time with family. Dan is an avid fan of all sports teams from his hometown, Cleveland, Ohio.


Ms. Catherine Durham serves as an administrative aide and Speech Pathologist with over 20 years of experience. She has worked in a variety of settings to include public school systems, hospitals, private practice as well as owning her own LLC in speech pathology.  She earned her Master’s degree at St. Louis University in Communication Disorders.  Her favorite age group to work with is middle and high school.  She was awarded a leadership award in 2017.  She has presented at local technology seminars in the area of Augmentative Communication Systems.  During her free time, she teaches cycle classes at a local gym.  She and her family are St. Louis Cardinal fans and travel to see the Cards as often as they can.




Ms. Jamie Jackson has been at Deep Run High School as a counselor for the past 17 years.  This year she will begin a new role as the School Counseling Director.  She earned her undergraduate degree in Family and Child Development with a minor in Psychology from Virginia Tech.  She then earned her Master’s degree in Marriage & Family Counseling from The College of William & Mary.  She stayed in Williamsburg and worked as a Substance Abuse Counselor for a short time before moving to Richmond to be with her husband Michael Jackson.  They have two sons who both attend Henrico County Public Schools.  She enjoys crafting, organizing, and planning fundraising events.




Mr. Michael Kidd spent his first 10 years in education as a teacher, coach, athletic director, and department chair in Hanover County before coming to Henrico in 2017.  He received his Bachelors Degree in Health, Physical Education, and Exercise Science from Virginia Commonwealth University and his Master’s degree in Sport Management and Administration from West Virginia University.  Michael and his wife Kelly have two beautiful daughters Audrey and Ella.  Michael’s goal is to implement a successful athletic/activities program where all students, student-athletes, and coaches have the opportunity to compete and participate in a safe and supportive environment.  Understanding the importance of community, sportsmanship, and professionalism is a top priority.  Michael likes playing golf and spending time with his family and friends.  Go Wildcats!

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