Dr. Bailey Stepping Down After 25 Years of Dedicated Leadership

After 25 years of unwavering dedication to the students, educators and families of the Issaquah School District, Dr. Dana Bailey has announced that she will be embracing her next professional challenge and departing at the end of the school year in June 2025. Bailey has always placed students at the heart of her work, and while she leaves behind a remarkable legacy of innovation, leadership and advocacy, she remains committed to supporting the district’s mission in the next chapter of her career. 

“We thank Dr. Bailey for her years of dedication and leadership in advancing student achievement and supporting educators,” said Superintendent Heather Tow-Yick. “Her impact has been profound, and her passion for removing barriers to student success has left an enduring mark on our district. In addition, she stepped up during a critical transition period to provide steady and creative leadership, while providing invaluable support to the organization to launch into the future as we navigate a new set of opportunities and challenges. Her contributions have strengthened our district, and we are grateful for her service.”  

Bailey’s career in education began in 1989, inspired by a deep-rooted family legacy of teaching. From her early years as a teacher at Ordway Elementary to her time as an assistant principal at Pine Lake Middle School, and later as the founding principal of Pacific Cascade Freshman Campus, she has consistently championed innovative programs that empower students and educators alike. Whether it was building a brand-new campus, supporting music and STEM programs, or ensuring students with disabilities received the support they needed, she faced every challenge as an opportunity to make a difference. As a district administrator, Bailey has played a vital role overseeing key leaders that supervise principals, pedagogy, curriculum adoption, special services and implementing inclusive learning environments to ensure every student can thrive and learn from one another. 

Reflecting on her tenure, Bailey shared, “I have been honored to serve students and work with exceptional teachers, leaders and families. When I look back to when I first became a school leader, I am reminded of the deep collaboration and daily inspiration from my middle school team, who reinforced my belief that when you keep students first, everything else falls into place.” Early in her career, Bailey recognized the quality of a student's teacher is the most critical factor in their academic success and can even inspire some students to become educators themselves. 

“It was a privilege to know Dr. Bailey in two different capacities: as my principal when I was a freshman at Pacific Cascade Freshman Campus and as my boss when I started my first job teaching at Pacific Cascade Middle School. As one of her students, I admired her energy, fairness and dedication to our school. When I was hired by her as a first-year teacher, I felt supported and encouraged to take risks, challenge myself and my students, and ask for help. Dr. Bailey has left a lasting impact on me, Pacific Cascade, and the Issaquah School District.  I am a better (and more data-driven) teacher because of her,” said Heidi Fielden, Pacific Cascade Middle School teacher.  

Bailey expressed deep gratitude for the support she has received throughout her career. “I am thankful to Superintendent Tow-Yick for her belief in my work, past superintendents, current and past School Board members, mentors, school leaders, families and most importantly the students who have made this journey so rewarding,” she said. “As many of my colleagues know, I am married to a long-time educator and a parent of five children who have all graduated college, and some are beginning to start their families. It is time to travel and spend more time with each of them,” Bailey shared. “While I am moving on, my heart remains with this district, and I look forward to contributing in new ways as my passion for tackling complex challenges and finding creative solutions in education will continue. I’m excited to see what comes next.” 

As Bailey prepares to transition, Tow-Yick reaffirmed the district is committed to stability and continuity. “With a solid foundation in leadership, curriculum development and operational excellence, ISD is well-positioned to ensure a smooth transition by building on past successes that drive innovation to support student success.” 

The district will evaluate and determine the best leadership model to advance its vision and commitment to educational excellence, providing regular updates to staff, families and the community throughout the transition process.