Where School Meets Community
Simon Williams

Simon Williams

Founder & CEO- Simon Williams is a graduate of Portland High School and earned his bachelor's degree in Kinesiology and Physical Education at the University of Maine. After playing six years of professional baseball, three with the St. Louis Cardinals Organization, Simon joined the Peace Corps serving in Ukraine as a youth development volunteer for 27-months. Upon leaving Ukraine Simon traveled to Thailand where he studied for and earned his yoga teacher's certification.  Since returning home he has worked as an ed-tech in the Portland School System. Aside from his day job, Simon coached baseball at Bowdoin College and boys soccer at Portland High School and served as co-president of the Maine Peace Corps Association. Simon is passionate about community engagement, volunteerism, mentoring, and inspiring kids. He lives with his wife Betsy in South Portland. They enjoy early morning bike rides, coffee, and the beach. 



To connect the world’s schools with the caring adults of their communities.


For every child to wake up inspired to go to school, feel safe and engaged when they are there, and to leave each day feeling like they contributed to something greater than themselves.


SchoolSquare was founded in 2015 as a not-for-profit organization with a 501c(3) status. Its primary mission was connecting mentors and role models with students and educators in order to help link young people’s academics and interests with community experts, resources, strengths, and supports. In its initial 18 months of operation, SchoolSquare, developed a Board of Directors, launched its MVP in Portland Public Schools with 10 teachers and 30 volunteers, hired a UX designer to create its new platform, and sought funding from various foundations and businesses for the development of a platform to register, vet, connect, and schedule community volunteers with classroom teachers. During this period, its founder, Simon Williams, conducted over 200 interviews with local teachers, school administrators, city officials, college and university staff and administrators, business owners, nonprofit leaders, and foundation members and staff.

Although, SchoolSquare found some initial supporters for the concept, sufficient funding was not forthcoming to enable it to fully realize its vision of developing a solution to help address community volunteerism in schools. After several months of evaluation and discussion with various people, organizations, and businesses, SchoolSquare determined to convert to a for-profit business model and to seek private funding to fulfill its mission.

In the Fall of 2018 SchoolSquare raised $25,000 by way of a successful Kickstarter campaign. Next, SchoolSquare’s MTI TechStart Grant was approved and it began its Customer Discovery work. This work focused on identifying potential customers, their priorities, problems, and establishing product-market fit. Simon Williams, interviewed 32 teachers, school principals, school-district superintendents, business leaders from January 2018 to June 2018. Simon learned about the current priorities in Maine’s education and business communities, the challenges they face, and is confident that SchoolSquare has identified its product-market fit.

Currently, SchoolSquare is beta-testing its software at Longfellow Elementary School and Casco Bay High School in Portland (Maine) Public Schools.