Phone: 919-929-2188 ext 31404


Degrees and Certifications:

Principal Tiffany Cheshire


My name is Tiffany Cheshire and I am the proud Principal of Phillips Middle School.  I have worked in education since 2005 and have been at both the elementary and middle school levels.  I went to Appalachian State for my undergrad degree and went to UNC-Chapel Hill for my Masters in School Administration.  My husband, Kevin, and I have been married for 16 years and we have two children- Quinn, 9, and Brooks, 6.  Our family are huge UNC fans and if we are not at athletic events, we’re usually talking about athletic events.  I enjoy baking and quilting, while listening to audiobooks.

My leadership style comes down to relationships and doing things with people not to people.  I try to be collaborative and transparent with decisions as much as possible.

Phone: 919-929-2188 ext 31237


Degrees and Certifications:

Assistant Principal Glenn Estacio


My name is Glenn Estacio, and I am excited to start my second year as an assistant principal at Phillips! I am a life-long Chapel Hill resident and have worked in education since 2008. I have been married to my wife, Sandy, for 16 years, and we are the proud parents of two children: Henley and Cooper. I am a sports enthusiast, and playing disc golf and lacrosse are two of my favorite pastimes. I also coached lacrosse for nearly 20 years. I taught 7th grade science as a teacher, and also spent 2 years as an assistant principal in Durham.

My leadership vision is built on 3 core beliefs: the importance of strong relationships, building leadership capacity for staff and students, and developing a school culture that values continuous improvement. I am eager to continue to put in the work to help the team make Phillips the best middle school in the area.

I am looking forward to an amazing year. I hope to be able to provide a compassionate ear to listen to you, a strong shoulder to lean on, and helpful advice and assistance whenever you may need it!

Let’s go Falcons!

Phone: 919-929-2188 ext 31391


Degrees and Certifications:

Assistant Principal Dr. Shanice Harrington


My name is Dr. Shanice Harrington, and I am excited to continue to serve in the role of Assistant Principal for my second year!  CHCCS is where I started my career in education as a first year teacher. Over the years, I have had the privilege of serving in additional roles including a mentor for affinity groups, equity team member, equity coach, SIT co-chair, and many other roles. This year, I begin the journey of year number 12!


For undergraduate studies, I attended North Carolina Central University where I obtained my bachelor’s degree in elementary education with a concentration in communication disorders.  I then obtained my master’s degree from the University of North Carolina at Chapel-Hill in Special Education, and my doctorate degree in Educational Leadership with a concentration in equity and social justice from Western Carolina University.   


Aubrie, my six year old daughter, is the light of my world.  We enjoy creating new memories and going on adventures together.  She keeps me busy with her competitive cheer.  When we are not in cheer practice or traveling for competitions, I can be found in my kitchen trying out new recipes or with my airpods popped in, listening to a new book on Audible or my favorite R&B artists.


Creating equitable opportunities for all students and families is at the center of my philosophy.  I am eager for the 2023-24 school year as I continue to extend my philosophy to our Falcon Family!