Canterbury’s dedicated college guidance team — Cindy Lyons, Melissa Wilson, and Amanda Cross — works closely with students and families throughout the college planning and application process.
College Guidance
Meet Melissa Wilson
Assistant Head of School for College Guidance
With 38 years of experience in college guidance and 18 years at Canterbury, Melissa Wilson brings extensive expertise, compassion, and a deeply student-centered approach to helping young people navigate the college process. As Canterbury’s Assistant Head of School for College Guidance, Melissa believes that college counseling is about far more than applications and admissions - it is about knowing, celebrating, and empowering each student as they take their next best personal step.
Melissa earned her Bachelor of Science in Individual & Family Studies from The Pennsylvania State University, University Park, and her Master of Science in Counseling from Southern Connecticut State University, along with additional certification as a School Counselor.
Before joining Canterbury, Melissa served as a college counselor at Branford High School and Old Saybrook High School, worked as an independent college and career consultant through College Knowledge, and served as an IB Counselor at Cape Coral High School. Throughout her career, she has developed a particular expertise in personalized college searches, the application and essay process, college admissions, and empowering students to approach the college process with confidence and integrity. She was nominated and selected for the Golden Guide Award from the University of Notre Dame in recognition of excellence in guiding students and demonstrating integrity in the college admissions process.
“College counseling is about helping students make the next best personal step.”
At Canterbury, Melissa has built a comprehensive College Guidance program rooted in love, kindness, resourcefulness, compassion, optimism, and reality. She begins working with families as early as eighth grade through seminars and individual appointments, providing students and parents with the knowledge and support they need to make informed decisions. Her goal is to make what can feel overwhelming approachable, purposeful, and even fun.
Melissa believes that every student deserves to feel valued and empowered throughout the college journey, regardless of their grades, goals, or where they are in the process. She takes the time to listen, answer questions, celebrate individuality, and help students see that they don't have to be perfect to pursue excellence. Her College Guidance office is intentionally a place where students can “chill,” ask questions, get tangible help, and feel comfortable being themselves.
For Melissa, the greatest reward of college counseling is not a particular college acceptance or professional accomplishment - it is seeing the smiles on her students’ faces when they leave her office. She is grateful to be part of the Canterbury community and considers it a privilege to help students and families navigate an important transition in their lives with confidence, joy, and a sense of possibility.
Meet Cindy Lyons
Director of College Guidance
For Cindy Lyons, Canterbury School is more than a workplace - it has been a part of her life for decades. Cindy joined Canterbury as a second-grade student in 1989 and graduated as a proud member of the Class of 1999. Now, as Canterbury’s Director of College Guidance, she brings that lifelong connection to her work with students and families, along with extensive experience in higher education and student support.
Cindy earned her Bachelor of Arts in Elementary Education and Master of Education in Curriculum and Instruction from Florida Gulf Coast University. Before joining Canterbury, she spent more than 10 years at FGCU, where she served as Assistant Dean of Students for Student Conduct. During her time at the university, she also served as Assistant Director of Greek Life during its early expansion, managed the Dean of Students’ Office Care Team, supported students in crisis, and served on numerous university committees, including the Fee Appeal Committee and Behavioral Consultation and Assessment Team (BCAT). She also reviewed disciplinary clearances for the Admissions Office, providing her with valuable insight into the higher education environment and the college admissions process.
Cindy has been part of the Canterbury staff for 11 years, serving in a variety of roles before joining College Guidance, including Executive Assistant to the Head of School, Registrar, and Community Service Coordinator. She worked alongside Melissa Wilson for six years as Registrar and College Guidance Associate before becoming Associate Director of College Guidance, a role she held for two years before becoming Director.
Cindy’s background in higher education and her deep understanding of Canterbury make her a trusted resource for students as they navigate the college process. She works closely with student-athletes on the NCAA Eligibility Center and is particularly knowledgeable about the Florida Bright Futures Scholarship application. Cindy is a member of the National Association for College Admission Counseling (NACAC) and holds a Professional Certificate in Coordinating a Dynamic Post-Secondary School Counseling Program from NACAC.
“One of the department’s greatest strengths is matching students with an institution that fits their unique skills and goals for the future.”
At the heart of Cindy’s approach is a desire for every student to feel supported, comfortable, and confident throughout the college process. She believes in honesty, approachability, and finding humor and fun along the way. By getting to know each student’s unique skills, interests, and goals, Cindy helps students identify colleges and universities where they can truly thrive.
Her connection to Canterbury is personal in every sense of the word. Cindy is not only a Canterbury alumna and longtime employee, but also a parent in the Canterbury community, and her husband has served as a Canterbury coach for many years. She is passionate about the school’s community and considers it a privilege to help guide Canterbury students toward their next chapter.
Meet Amanda Cross
Registrar and College Guidance Associate
Amanda Cross brings a unique combination of business experience, institutional knowledge, and a genuine passion for supporting students and families to her role as Registrar and College Guidance Associate at Canterbury School. She holds a Bachelor of Arts in Economics & Business Administration from Rhodes College and an MBA in Marketing from the Kelley School of Business at Indiana University.
Before joining Canterbury, Amanda spent seven years working in marketing, business development, and auditing for companies in the financial services, advertising, and chemical industries. She later brought that experience to Canterbury, where she has spent the past 20 years building a deep understanding of the school, its programs, and the students and families who make up the Canterbury community.
Amanda and her husband first became part of the Canterbury community in 2004, when he joined the Upper School faculty as a history teacher. A few years later, Amanda joined the school as Office Manager, beginning a Canterbury career that has included a variety of roles and responsibilities. Throughout her time at Canterbury, she has become known for her exceptional organizational skills, meticulous attention to detail, and ability to bring calm and clarity to even the most complicated tasks.
Amanda has worked closely with Melissa Wilson and Cindy Lyons in the Upper School for many years, and her transition to College Guidance builds naturally on that experience. Her expertise includes scheduling, course and curriculum planning, grade reporting, logistics, and event planning. She brings a calm, reassuring presence to the College Guidance team and has a particular talent for finding thoughtful solutions to the many details and moving pieces involved in the college process.
As the parent of a recent Canterbury graduate, Amanda also brings firsthand experience navigating the college application process with her own family. She understands how meaningful thoughtful guidance and support can be for both students and parents, and she brings that perspective to her work with Canterbury families.
“She understands how meaningful, thoughtful guidance and support can be for both students and their families.”
Amanda feels especially honored to now work alongside Melissa and Cindy, whose wisdom and expertise made an invaluable difference to her own family during the college process. She admires their extraordinary ability to support and guide students and families and feels privileged to contribute her own experience and perspective to such a dedicated team.
For Amanda, College Guidance is an opportunity to combine her love of the Canterbury community with her strengths in organization, problem-solving, and supporting others. She is grateful to help students and families navigate the college process with confidence and clarity, bringing warmth, enthusiasm, and a genuine commitment to making the journey feel manageable and supported every step of the way.
