Matt Eskin - Education Consultant

Matt Eskin

is an educational consultant with over 30 years of experience as an educator and school leader in both day and boarding schools. He specializes in helping families navigate complex educational challenges—whether at home or within the school system—particularly when the relationship between school and family is tested.


Matt supports families in making informed decisions about the settings and services that will best help their child thrive. His expertise lies in identifying good-fit schools, understanding what resources are available to meet a student’s needs, and coaching parents on how to engage with both student and school in ways that lead to more positive outcomes. Over the years, he has built trusted relationships with therapists, psychiatrists, reading specialists, and school administrators—allowing him to recommend, curate, and coordinate services that truly support students and families.

Matt earned his Master’s in School Leadership from Harvard University in 2006, where he received the Intellectual Contribution/Faculty Tribute Award—an honor given to the student who most significantly contributed to the intellectual life of the community. He went on to serve as a Middle School Director and Associate Head of School, deepening his understanding of both individual and systemic factors that shape student experiences and outcomes.


Matt lives in Philadelphia, PA, with his wife, two children, two playful dogs, and a handful of chickens. He enjoys cooking, mountain biking, rock climbing, and the occasional building project around the house.

A blue graphic of a compass overlapping a large letter C. The compass also turns the C into an E, representing "C-E", for Craftwell Education.

  • "From the moment we first met Matt, we knew we were in excellent hands. Matt was honest about what we could expect, transparent about the process, and incredibly supportive every step of the way. Matt understands kids and families, brings a wealth of knowledge and experience of the academic landscape to his client relationships, and provides incredibly insightful guidance. Most importantly, Matt is truly a terrific person who we enjoyed engaging with on a personal level."

    Sam & Derek

  • "...what makes Matt a real top-notch expert is that as a long-time teacher and coach himself, he also knows how to talk with and inspire kids. He has a real “can-do” attitude towards life and our kids appreciated that someone other than their parents believed in them..."

    Sara C.

  • "We’ve called on Matt for a range of educational advice. Each time he generated creative ideas, had a flexible working style, and kept things on track with regular meetings and check-ins. We are extremely grateful to Matt for his caring, straightforward approach, and the help he has provided our family."

    Tom S.

  • “Our teenage son has been struggling with anxiety and has been refusing school. Matt has been such a great help to us, talking us through our options, listening to our concerns and asking questions, never with an ounce of judgment. We have appreciated his thoughtful consideration of our current struggle, as well as his wealth of knowledge of resources. We would absolutely recommend that anyone reach out to Matt if they are struggling to know the best way forward for their child.”

    Moira H.