Ashley Leonard

As the Founding Associate Director of the To&Through Middle Grades Network, Ashley N. Leonard will lead the development of all aspects of the network, working closely with schools, partners, and the To&Through team. 

Leonard began her career in the private sector when she was selected as one of 15 individuals to participate in a two-year management development program at Kraft Foods. After four years gaining expertise in sales, customer service, consumer analytics and category management, Leonard acted on her long-standing passion for educational access and equity and pursued a full-time career in education. Leonard began education career at Chicago Public Schools (CPS) where she led a number of district-wide strategic initiatives including the successful launch of Mentoring the Next Generation, a program that paired more than 500 kindergarten and eighth grade students with CPS employee mentors.  After CPS, Leonard served as Special Projects Manager at The Chicago Public Education Fund (The Fund) where she was responsible for collaborating with CPS leadership to support principal talent management and developing the strategy to support fundraising efforts for the next phase of The Fund’s work. 

Most recently, Leonard was the Executive Director for Spark in Chicago, a career exploration and self-discovery program that helps middle school students understand, experience, and pursue what’s possible. It was in this role that her passion for the middle grades was solidified as she saw how Spark’s unique blend of social emotional learning, social capital, and connections to caring adults changed the trajectory of middle schoolers across Chicago.  Leonard holds a Masters of Education in Education Policy and Management from the Harvard Graduate School of Education and a Bachelor of Arts in Sociology from Vassar College. She is also proud alumna of the Surge Fellow and was part of the inaugural Education Pioneers Yearlong Fellowship.