Board of Directors

Margaret Crenshaw is a Realtor with The Kiser Jetton Team at eXp Realty and a 50-year islander. She is on the Board of Directors for the island’s newest community theatre, Sea Glass Stage Company, and is a contributing writer for CH2 Magazine, and Co-Host of the “Eat It And Like It” podcast “Mondays with Maggie”. She is a Hilton Head Prep Alumni Past President, Vice President and is currently in her 20th year as a board member. Margaret has one daughter, Ellery Margaret Newcomer-Crenshaw ‘15.

Addison graduated from Hilton Head Prep as a Lifer in 2006.  After graduation from Prep she attended the University of Georgia where she received her B.A. in Marketing in 2010.   Addison married Andrew Cook in 2014 and they have two beautiful boys, Harris '34 and Alden '38.  Addison is the former Membership Director at the SCYC.

A lifer at Hilton Head Prep, Andrew credits much of his success to his foundation provided during those 12 years. The lessons he learned in the classroom and as a four-year letterman on the Tennis and Cross Country teams not only instilled a love of Prep in his life, but taught him the importance of giving back to the community. When he moved back to Hilton Head Island after studying engineering at Maryville College, Andrew began giving back to Hilton Head Prep. He became involved in many Prep activities, and wears a Prep logo on his shirt proudly around the Island. He and the members of Cranford Hollow have donated a free concert to the Jubilee auction six times, played at the Back to School Bash, and played along with students at the Prep Strings Concert. He is involved in many non-profit organizations on the Island including NAMI, Friends of Caroline Hospice, Hilton Head Humane Association, and The Island Rec Center. Most recently, he helped raise money for Hurricane Matthew disaster relief. Andrew lives on Hilton Head Island with his wife, Samantha, and their son, William, a future Prep dolphin.

Keylan grew up on Tupelo Road and was able to walk to Hilton Head  Prep.  He competed in football and soccer, attended Intel’s International Science and Engineering Fair and played cello in the school orchestra.  His mother, Krista, has been a teacher at Prep for over a decade, and his sister, Brittany ‘20 was an “HHP Lifer”.

After graduating in 2015, Keylan attended the University of South Carolina and received a degree in Visual Communications and Marketing.  He has since returned to Hilton Head and runs a successful photography and videography company.  He attributes much of his success to the wonderful foundation that his teachers provided him while attending Hilton Head Prep.

Keylan continues to work with Prep regularly and provides media services for Prep’s marketing, performing arts, and graduation ceremonies.

Meg, an HHP lifer, graduated from Hilton Head Prep in 1998.  She and her husband, Zeno, have three children that attend Prep.  Berkeley '27, Victoria '30, and Hank '32.

Meghan Brown Gregory graduated from Prep in 2009 and went on to Clemson, finishing her degree in 2013. After spending 10 years in New Orleans, she moved back to Hilton Head in 2024 with her husband, Heath, and their two cats to be closer to family, including her sisters, Mackenzie (’12) and Riley (’15). She is currently the Director of Finance at Historic Mitchelville Freedom Park.