Wildflower Montessori started in January 2014 as a single shop-front early childhood education program created by MIT Media Lab professor Sep Kamvar in partnership with two Montessori veterans, Mary Rockett and Katelyn Shore. Wildflower quickly captured the attention and imagination of parents, teachers and community leaders in Massachusetts and beyond. Over the next 2 years, the growing network of teacher leaders helped start 7 additional Wildflower schools in Massachusetts and Puerto Rico, created a network of support and coaching based in Cambridge, developed a set of principles that would define what it means to be a Wildflower school and laid out a vision for a new type of school network that empowered teachers and harnessed organic processes to grow and improve. At the same time, Sep’s team at the MIT Media Lab developed prototypes for using technology to support teachers with school administration and student observation.

In the spring of 2016, Matt Kramer joined the team as The Wildflower Foundation’s first CEO after 10 years of leadership at Teach For America. Wildflower moved from a project within the MIT Media Lab to an independent 501c3 organization with a network of schools that had grown to 11 schools. Recognizing the challenges of creating intentionally diverse schools without public funding, Wildflower developed models for creating schools as charters, voucher-supported independent schools and through district partnerships.