Debbie Boileve, Executive Director of Cherry Preschool, also taught in the Yellow Room since Cherry Preschool was founded in 1992, and was a member of the original Cherry Preschool Board.  Before becoming Director, Debbie was the curriculum coordinator for the preschool.  During the 2006-07 school year, she mentored the staff through reaccreditation by the Academy of the National Association for the Education of Young Children.  Debbie has a degree in early childhood and elementary education and has worked professionally with young children for the past 30 years.  She has worked as a day care teacher, teacher/director of a camp program, art resource instructor, curriculum coordinator for a home day care network, and preschool teacher.  In 2009, Debbie was awarded a Level II Illinois Director's Credential. This year, she is chair of the Evanston Early Childhood Directors’ Council.  Debbie is the parent of two adult children, one in college and one in veterinary school.

Rhonda Cohen is beginning her seventeenth year at Cherry and her thirteenth as Child Development/Inclusion Director.  In addition to her general administrative duties, Rhonda works with the staff to support the inclusion of children with special needs and children receiving outside support services.  Rhonda is also available to consult with parents on issues related to their children’s development.  The parent of two adult sons, Rhonda has an education degree as well as a Master’s Degree in special education and Ph.D. coursework in educational psychology, child development and speech and language acquisition. She has worked as a preschool and primary education teacher as well as a teacher of hearing impaired children.  Rhonda was the recipient of the 2004 Childcare Network of Evanston early childhood award.

Maggie Hessler is beginning her eighteenth year as Site Director.  A member of Cherry Preschool's founding board, Maggie has a background in business and social work.  She is the parent of three adult children, Zachary, Jeremy, and Tess (who was in the first graduating class at Cherry).  In addition to managing all aspects of building operations, Maggie helps to organize day to day operations and can be found there every day working with Debbie and Rhonda.  Maggie also puts her background in social work and early childhood education to good use as the administrative liaison to the Community Outreach Committee.  For the past four years, Maggie has put a great deal of time and energy into establishing and maintaining the Latino Parent/Child class.

Jeanette Hollingsworth is starting her third year Administrative Assistant in the morning and teacher aide in the 4 Afternoon Multiage Orange Room class.  She has been involved with Cherry Preschool since 2003.  She and her husband, Rich, have three daughters who are all Cherry graduates and attend the TWI program at Washington School: Nancy is in fifth grade; Sydney is in third grade; and Lily is in second grade.   During the years her children attended Cherry, Jeanette was a frequent volunteer and served two years on the Board.  She has been a substitute teacher for the past three years.   Jeanette has served as PTA Co-President at Washington School and also teaches American Red Cross classes and coaches swimming at the YMCA.

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Laurie Levy, Cherry Preschool’s Founding Director, is working part time as Communications Coordinator.  An active member of Evanston's early childhood community, Laurie twice chaired the Evanston Early Childhood Directors’ Council, co-created the Guide to Evanston Early Childhood Programs, served on the District 65 Task Force on Early Childhood Education and the Evanston Community Collaboration for Early Childhood Education.  Laurie received the 2002 Childcare Network of Evanston early childhood award.  She has a Master’s Degree in early childhood administration, and has taught in preschool classrooms as well as having been a high school English teacher.  She is the proud parent of three adult children and the devoted grandmother of Cherry alums Ella and Tessa, their little sister, Maya in the 3 Morning 3’s Orange Room, and three year old granddaughter, Ava, and infant grandson, Tyler, who live in Indianapolis.

Shirlene Ward, Cherry's Financial Manager for the past twelve years, handles all the school's bookkeeping, student medical records, budget analysis and preparation, and generally anything that requires a spreadsheet.  She is the parent of two Cherry alumni (Dan now in college and Paul attending ETHS) and lives in south Evanston with her sons and her husband, Kevin Kipp.  In her former life, she was a music librarian at Northwestern University, and has degrees in Piano, Musicology, and Library Science.  She currently devotes her volunteer hours to chairing the board of The Orion Ensemble, a chamber music group of five remarkable women who perform in Evanston, Chicago, and Geneva.