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Leadership Update

On May 11, 2022, Siena Founder and Board Chair Erik Heyer announced that after 16 years as founding Head of School, Jilly Darefsky will advance to oversee the entire organization’s curriculum and instruction, program innovation, strategic initiatives, and the development of the school’s leadership team and exceptional faculty as Executive Head of School, effective July 2023. Educational Directions, a leading national independent school search firm, will conduct the process to identify Siena's next outstanding Head of School, and we're excited to attract high-quality applicants to this position.

As the search progresses, please refer to this page for updated communications and information.

Letter to the Community

Over the past sixteen years, The Siena School has steadily grown into a nationally recognized leader in dyslexia education for students with learning differences. This year, Siena now serves almost 175 students and 50 faculty and staff on two campuses. Our consistent focus on offering the highest quality, research-based programs has always been a by-product of our exceptionally talented and hard-working team and community. Especially with the challenges presented these past few years, we cannot thank each and every member of the Siena family enough!

With our commitment to continuous improvement and the growth of the school, The Siena School is excited to announce the next step in the organization’s development. Over the next 18 months, Jilly Darefsky, Executive Head of School and a member of the founding team, will be transitioning to oversee the entire organization’s curriculum and instruction, program innovation, strategic initiatives, and the development of the school’s leadership team and exceptional faculty.

For the upcoming 2022-23 school year, Jilly will continue as the day-to-day Head of School in Silver Spring. We will shortly begin a national search for the next Head of School, who will begin July 2023. The multi-campus model has emerged as a national trend for leading independent schools to support mission-driven growth, and this change helps support similar opportunities at Siena.  

For over 16 years, Jilly has been an unwavering leader and champion for Siena’s students, faculty, program, and level of excellence. Looking ahead to the next decade, we are excited for the opportunities this new role provides both her and Siena. Jennifer Betts, Head of School in Northern Virginia, is another key member of Siena’s leadership team and expertly led the successful new campus opening this year. Together with the new Head of School in Silver Spring, Jennifer, Jilly and our team will be well positioned with more time, resources, and opportunity to support and grow Siena’s nationally recognized programs. ​

To help us find the next outstanding leader of our Silver Spring campus, the board has engaged Educational Directions, a nationally known executive search firm serving independent schools, and with special expertise in leaders and schools who serve students with learning differences. Dr. Jerry Larson and Dr. John Watson of Educational Directions will be visiting The Siena School on Tuesday, May 24th, and Wednesday, May 25th, to learn more about our unique school community and the leadership qualities we all value. Please be on the lookout for more details about the search soon.

This is an exciting time in The Siena School’s history. We are looking forward to our continued growth as a national leader in the education of students with language-based learning differences. Please do not hesitate to contact Jilly or me with any questions.


Erik Heyer
Founder, Board Chair, Parent (5th)

Frequently Asked Questions

The search for Siena Silver Spring’s next Head of School will begin immediately in partnership with Educational Directions.

This summer we will be undertaking candidate recruitment and screening, and we expect to identify top candidates in the late summer/early fall.

There will be several rounds of interviews. Finalists will spend time on campus with an opportunity to meet various community members—most importantly, our students and faculty/staff. Insights from the Siena community about the school are critical to the success of this search.

Siena community questions concerning the search process can be directed to

Inquiries or recommendations should be directed to Educational Directions:

It is our objective to name the next Head of School for the Silver Spring campus in late fall/early winter. Once Siena Silver Spring’s new Head of School is named, Ms. Darefsky and the team will begin the transition and onboarding process for the new Head. The next Head of School for the Silver Spring campus will assume their duties on July 1, 2023.

No. Ms. Darefsky will continue day-to-day leadership of Silver Spring through the end of the 2023 school year, and as Executive Head of School she will continue thereafter to maintain overall responsibility for Siena’s curriculum, program, and operations. Our faculty, staff, and administrators remain committed to fulfilling Siena’s mission and providing our students with the excellent educational experience that Siena has established.

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