Lakeview Head Leaves Record of Accomplishments

Dr. Montgomery was named head of school in November of 2019 and moved with her husband to Gainesville from Chicago, where she had been Director of the Osher Institute at Northwestern University. Her appointment to Lakeview came as the result of an extensive nationwide search. In addition to leading the school, Dr Montgomery also teaches an Advance Placement course in Comparative Government & Politics.

Dr. Montgomery’s husband, Chris Hasselbring, a professional musician, joined the Lakeview fine arts staff and has been responsible for expanding the Lakeview instrumental music program to include brass, woodwinds and percussion, and Brazilian samba. Both Chris and Dr. Montgomery will fulfill their teaching obligations this school year before their June 30 departure. 

“Chris and I made the move to Gainesville and Lakeview because we saw a passion for learning at Lakeview and a family atmosphere that was palpable,” said Montgomery.  “We had enormous hopes for the future and were excited to make the move.”

The pandemic brought unexpected upheaval to their hopes and plans as they struggled to manage long-distance health care for aging parents as well as see to the health and wellbeing of their teenage and adult children. “We know that the pandemic led to an increase in social-emotional and mental illness in young people, and our children were no exception. Restrictions on travel made it difficult for us to go back and forth to Chicago to support our children through wave after wave of challenges,” said Montgomery.

In addition to steering the school through the global pandemic, Montgomery’s Lakeview accomplishments include appointing a Dean of Academics and Instruction to revise and align the curriculum, creating a permanent online school, appointing a Senior Director of Development, revising internal policies and business practices, enhancing on-campus security, technology upgrades, and facility improvements, including the new practice field and upcoming beautification of the front of the school. Also, under Montgomery’s leadership a strategic planning process is underway that will guide Lakeview Academy for the next five years.

Montgomery’s style of leadership was marked by involvement with students from preschool through 12th grade.  She was a daily fixture assisting with drop off and pickup of students, appeared in Lakeview’s fine arts performances, and charmed students with her native British accent and stories of her homeland.

“I have been incredibly fortunate to be supported by dedicated Lakeview staff, faculty, administration, parents, and, of course, the board of directors,” said Montgomery. “I will miss this place terribly. I truly believe that Lakeview’s future is bright.”

The Lakeview Board of Directors has unanimously named John Simpson as new head of school. Simpson has served in a variety of roles at Lakeview over the last 20 years and was most recently interim head of school prior to Dr. Montgomery’s appointment. He has worked side-by-side with Dr. Montgomery for the past two years and it was decided he is the best choice to make a seamless transition and continue the school’s growth, said Kilroy.