Head of School Transition

Head of School Transition

In October 2022, the Head Search Committee began the extensive process of recruiting the strongest and best-matched candidates for our school via a national search in partnership with a consultant from Educators Collaborative. The Board of Directors is very excited to announce that Darren Holgate has assumed the role as our next Head of School beginning July 1, 2023. Pinecrest School is thankful for Nicole McDermott’s 18-year-long tenure as the Previous Head of School and her continued efforts until August 11, 2023 as Acting Head in advance of Darren’s permanent arrival to Pinecrest on Monday, August 14, 2023. Read more below and continue to visit this page for updates on the Head of School Transition process.


May 11, 2023


Dear Pinecrest Community,


I am thrilled to be joining you as your next Head of School this summer, and I am truly honored to become a member of this exceptional community. It is with great enthusiasm that I begin my tenure here, and I am looking forward to working closely with all of you as we strive to grow the school and provide the best possible education for our students.


I bring with me a wealth of experience and knowledge from my previous roles in education both as a teacher and school leader, and I am excited to share my insights with the faculty, staff, and students here. I believe that a successful school is built on a strong foundation of collaboration, communication, and commitment, and I am confident that we can work together to achieve our shared goals.


As the next Head of School, I am committed to a culture of excellence that celebrates the achievements of every student and recognizes the hard work and dedication of our faculty and staff. I believe that education is a lifelong journey, and I am eager to help all of our students develop the knowledge, skills, and character they need to succeed in their future endeavors.


I want to thank so many of you for making me feel so welcome. I have been granted hugs of acceptance from the younger students as I visited their classrooms and words of eager anticipation from many

of the older ones. As you already know, the administrative team is phenomenal; they’ve worked hard during this transition by answering all of my questions and offering support and guidance. I have met one-on-one with many of the faculty and heard so many wonderful things; I’m grateful to be working alongside such a talented, knowledgeable, and caring team.


Ms. McDermott has created and sustained a school that any educator or parent would be proud to call their school. I am immensely grateful for her insights, experience, and grace. I know she will be leaving behind a strong legacy and I am eager to build on what she has accomplished.


Together, we can continue to foster a vibrant and dynamic community that inspires and challenges our students to achieve their full potential. I look forward to getting to know all of you and working together to make this school the best it can be.



Darren Holgate


March 2, 2023


Dear Pinecrest Community,


We are very excited to announce that Darren Holgate has enthusiastically accepted the invitation of the Board of Directors to be the next head of school at Pinecrest! We are thrilled to welcome Darren, his wife Julie, and their three daughters into the Pinecrest community.


In October 2022, the Search Committee began the extensive process of recruiting the strongest and best-matched candidates to our school via a national search, in partnership with our consultant, Tracy Bennett of Educators Collaborative. The Search Committee was excited and encouraged early on in the process. Interest in the position was incredibly high and the candidate pool was strong, and diverse.

From an initial candidate pool of eleven, the Search Committee narrowed the pool to eight semifinalist candidates who were invited to participate in confidential interviews with the Search Committee. Following these interviews, three finalists and their spouses/partners were invited to visit the school, where they met in a variety of formats with faculty and staff, parents, students, administrators, alumni, and Board members. After reviewing feedback from all stakeholders, the Search Committee voted unanimously to recommend Darren as the next head of school at Pinecrest. The Board of Directors met and discussed the Search Committee’s recommendation and unanimously approved the Search Committee’s recommendation.

While Darren will officially begin his headship on July 1, 2023, he will begin to visit campus in the coming days to learn about the school and get to know the community in partnership with Nicole and the Board of Directors. Please join us in extending a warm welcome to Darren when you see him on campus!

Darren brings to Pinecrest many years of experience as a teacher, Director of Academic Technology, Lower School Director, and Middle School Director. Darren holds a Bachelor of Education degree from England and a Master of Science degree in Educational Leadership and Technology Integration in Independent Schools from John Hopkins University.

During Darren’s educational career, he has been involved in virtually every facet of the school, including faculty growth and professional development, introducing new school-wide initiatives, such as Responsive Classroom for student’s social and emotional growth, serving on committees for VAIS accreditation, and importantly, successfully led Powhatan School through the pandemic in partnership with the Lower Division Director and Head of School. Darren’s wealth of educational experience, positivity, and passion for students and education make him an excellent addition to the Pinecrest community.

We are incredibly grateful for the community’s engagement throughout the search process. We thank all of you who welcomed and hosted our candidates and thoughtfully completed the feedback surveys after each visit. Your input was integral to the Search Committee’s recommendation to the Board, and we truly thank each of you.

We would like to extend a special thanks to our fellow Search Committee members who devoted many hours and care to the search process, and also extend our thanks to the Pinecrest Board of Directors for their outstanding leadership. We are also especially grateful for the guidance and support of our consultant, Tracy Bennett.

We want to sincerely thank Nicole, Cynthia, Ragan, Linda, and all the faculty and staff at Pinecrest for their time, feedback, and hospitality. The candidate visits would not have been possible without them.

Lastly, we want to say a special thank you to Nicole, for her 19 years of service to Pinecrest, and for supporting the search process from the very beginning. We are very grateful for her continued work and commitment to make the transition in school leadership a smooth one. Thank you, Nicole!


We are so excited to welcome Darren into the Pinecrest community and look forward to a bright future together.


Steve Donahoe, Board Chair, Co-Chair Search Committee
April Kreller, Board Vice Chair, Co-Chair Search Committee


Search Committee

Manisha Bhaskar

Steve Donahoe

Amelie Haden

April Kreller

Melissa Holder-Murray

Steve Rumpp

Nick Wakeman


April 27, 2023


Dear Pinecrest Community,


On behalf of the Board of Directors, we want to share an update with you about our Head of School transition. We are very excited that Darren Holgate will assume the role of our next Head of School beginning July 1, 2023, and we want to let you know that we are so pleased that we can retain Nicole McDermott longer than originally planned as she will be serving as the Acting Head of School from July 1, 2023 through August 11, 2023, in advance of Darren’s permanent arrival to Pinecrest on Monday, August 14, 2023. We are truly appreciative of Nicole and Darren’s partnership as they work to make the Head of School transition a smooth one.


Darren has another commitment this summer, one that he made before he knew of the opportunity at our school. Darren informed the Board of Directors of this prior to accepting the position as our next Head and we are working with him to accommodate this. Although Darren will not physically be at Pinecrest on a daily basis as our Head of School until mid August, he will be coming in throughout the summer and working remotely to ensure plans are in place for 2023-24 to be an amazing year. He will be communicating regularly with the school, administrative team, and Board throughout the summer and should you want to talk with him or meet in person please reach out to the school.


We are incredibly grateful for this additional time with Nicole and for her continued work and commitment to make the transition in school leadership as successful and seamless as possible.  We are also grateful for the time Darren has given, and continues to give, to Pinecrest in advance of his headship. This is Community!


We want to sincerely thank Nicole, Darren, Cynthia, Ragan, all of the faculty and staff, and the entire Pinecrest community for their support during this transition period. This is such a significant moment in time for our incredible school! As we look forward to the next few months, we are excited for another great summer at Pinecrest! If you have not signed up for summer camp yet, we hope your child(ren) will join us at our award-winning camp. Limited space is still available and details can be found here.


As we get closer to the summer, please look out for communications from Mr. Holgate and Ms. McDermott about how to reach them this summer and more details about the transition.




Steve Donahoe, Board Chair, Co-Chair Head Search Committee 

April Kreller, Board Vice Chair, Co-Chair Head Search Committee 

Click on a tree icon below to be up to date with the newest and previous updates.

Update 6.3.23

Update 5.11.23

Update 4.27.23

Update 4.24.23

Update 3.2.23

Update 1.24.23

Update 1.13.23

Update 12.13.22

Update 11.15.22

Update 10.20.22

Update 10.07.22

Update 09.19.22

Please continue to visit this page for updates on the Head of School transition.