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Jess Cihal

Associate Vice President, Learning & Strategy; Aspiring Leadership Programs Lead

Jess Cihal is Associate Vice President of Learning & Strategy at The Leadership Academy and serves as the Content Lead for the organization’s aspiring leader pathways, supporting teacher leaders, assistant principals, and principals. Jess has partnered with school and system leaders across Georgia, Kentucky, Maryland, Massachusetts, Minnesota, Nebraska, Nevada, New York, Oregon, South Carolina, Texas, and Washington D.C.

She brings deep experience leading complex, multi-year, multi-partner projects. She collaborates with education leaders to identify their specific opportunities and barriers and co-develop strategies to address challenges. In her work with aspiring leaders, she designs and facilitates pathway programs that strengthen leadership at all levels and cultivate cultures that help all school staff see themselves as leaders of student change. Among the unique programs she’s helped design and implement are a multi-year initiative for aspiring leaders centering multilingual learners and a systemwide leadership development system—spanning the creation of a leadership standards continuum, strengthened hiring and leadership development processes, and the launch of an aspiring principal academy.

Internally, she leads the project management team and oversees client engagement staffing, ensuring talent is thoughtfully aligned to make the greatest impact. She also leads the team responsible for The Leadership Academy’s internal employee learning and development, fostering a culture of growth and collaboration.

Prior to joining The Leadership Academy in 2012, Jess spent her early education career abroad, in teaching and education roles in Eastern Europe and Central America. She then spent six years working at a K-12 school in San Antonio, Texas.

Jess holds a Bachelor of Arts in English and Youth & Human Services from the University of Texas, San Antonio, and a Master of Public Administration in Public and Nonprofit Management from New York University’s Wagner School. She is based in Dallas, Texas.

Education leaders who have worked with me say that...

I encourage them to examine the systems that are driving the outcomes they seek to change, and that I support them in designing programs that balance long-term transformation with immediate wins. Also, that I’m attentive and dependable, because I listen carefully and follow through.

I know I’m making a difference with school and system leaders when…

I hear them say that data isn’t numbers, it’s people, and I see them bringing “street data” into the conversation—real stories like what students are talking about at lunch or what they hear walking the halls. It helps them design stronger systems, so all students feel seen and supported.

When I was a kid I wanted to be…

A teacher, like my granny. I absolutely adored her, not just for her strength or cooking or the fact that she sewed matching clothes for me and my dolls, but also because she often answered my questions with questions. She helped me reason out the answers for myself. Her technique is one I still use today!

Kendra Washington-Bass

Different Roles. Same Goal.

We believe every child’s school experience should prepare them for success in the classroom and the world, and we’re all in on supporting the leaders who can make it happen.

Meet the Rest of Our Team