Dr. Jaeger began his educational career as a secondary school social studies teacher, and he has been a university professor at both the undergraduate and graduate levels. His over thirty years of extensive school leadership have included Department Chairperson, Assistant Principal for Instruction, Principal, Assistant Superintendent for Instruction, Assistant to the regional District Superintendent, Deputy Superintendent for Curriculum, and Superintendent of Schools in four different systems and a New York State Board of Cooperative Educational Services (BOCES). These K-12 systems were unique and diverse, small and midsize suburban, multicultural and urban, and large and centralized. They ranged in size from 1200 to 12,500 pupils and from 175 to 1100 employees. The regional BOCES supported 13 school districts.

Throughout his career, Dr. Jaeger was an invited presenter at regional, state, and national conferences on such subjects as leadership team development in K-12 schools, strategic planning, data-driven school improvement, teacher and principal evaluation, coaching and mentoring employees for improved practice, arts-in-education, interdisciplinary instruction, and curriculum development. His ongoing educational consultant residencies have included extensive personnel training and strategic planning with both schools and not-for-profit organizations throughout New York City and New York State.. For eleven years, he was a member of the New York State Board of Regents Professional Standards and Practices Board and was its co-chair of the Higher Education Subcommittee.

Over decades, Dr. Jaeger served on multiple non-profit community boards of directors and professional advisory boards including chambers of commerce, educational foundations, regional and state arts councils, school study councils, and the National Urban Alliance. He is the recipient of awards for Excellence in Administration, as well as the National Parent Teacher Association's Honorary Lifetime Membership for distinguished service to youth, the L.I.F.E. Award from Literacy Volunteers of America, and the first Dutchess County (NY) Executive Award for school district arts-in-education programming.

In July 2020, Dr. Jaeger published Principals with Impact: 5 Leadership Roles to Improve Schools. The book is every school leader’s roadmap to transform staff collaboration and propel profound student growth.