Our Staff

Diane Smith

Director/Lead Teacher Kindergarten Class

Diane Smith is the founder and director of Countryside Montessori School and has 32 years experience teaching preschool age children.  She started her teaching career as a Suzuki piano and preschool music teacher in 1987 after receiving her Bachelor of Music degree from the University of Western Ontario and completing course work for a Master degree in piano performance.  In 2005 Diane received her Montessori Certification from the United Montessori Association.  Diane and her husband own and operate a crop farm in Addison Michigan, where they raised their 7 children.  Out of the classroom Diane enjoys hiking, cross country skiing, knitting, and spending time with her children and grandchildren.



Maria Cowan

Program Director

Maria received her Bachelor of Early Childhood Education from Lake Superior State in 2012. She has worked in Early Childhood Education for seven years, the last four here at Countryside. She enjoys reading, traveling, and spending quality time with her husband and sons.




Regina Olson

Primary Lead Teacher

Regina earned her Bachelor of Elementary Education  from Austria before moving to the United States. She has homeschooled her children for the past 20 years on their family farm just outside of Hillsdale. She enjoys reading, gardening and spending time with her children and grandchildren.



Tressa Stille

Primary Lead Teacher Afternoon

Tressa earned her Associate Degree in Early Childhood Education at Maranatha Baptist University in Watertown Wisconsin.  After  working at  the  University  Daycare  and  private  tutoring,  Tressa  joined  the  staff  at  Countryside  in the  summer  of  2018.  Tressa  enjoys  caring  for  her  pet  rabbit,  crocheting,  and  wood  working.



Nancy Livingston

Primary Teacher’s Assistant

After completing her Associate degree in Early Childhood Education, Nancy taught and became the program director of a daycare center. Nancy brings many skills to the classroom that she acquired while homeschooling her own four children. Nancy enjoys reading, gardening, and spending time with her children and grandchildren.


Interested in joining the team at Countryside? Please fill out the application here.