Jonathan Maiorano

Assistant Headmaster

Northern Oaks Lower School

“Curating experiences for teachers to pour into them and fill their cup as a kind of recompense for the countless ways they pour into their students is a remarkable and humbling responsibility that one cannot take lightly.”

The mission statement “to cultivate the hearts and minds of scholars through the pursuit of the Good, True, and Beautiful” is what initially drew Jonathan Maiorano to Great Hearts. He shared, “I looked through the website for close to three hours. It seemed too good to be true, a school dedicated to the joyful pursuit of the transcendentals I heard solely in the Greek dialogues of Plato and Socrates, and in Aristotle’s Nicomachean Ethics in a community of learners? Then, when I interviewed with Jerilyn Olson in an Irish Pub outside of Princeton University on a blistery and snowy Sunday evening, she asked to me teach her how to add fractions, despite her awareness of my major in Political Science, which both humbled and challenged me to communicate clearly and concisely, while eating Fish & Chips!” 



In serving across ten different roles with Great Hearts during his time, Mr. Maiorano rightly credits over ten individuals from which he drew inspiration. 

Shanna Siller

Assistant Headmaster

Northern Oaks Lower School

“I now have a greater role in the conversations and decisions that impact our faculty and community, and I hope to continue the intentional leadership my predecessors have modeled.”

Like many Great Hearts teachers, Shanna Siller first came to Great Hearts as a parent, searching for a new school for her four children as the family relocated to San Antonio. “I was initially drawn to Great Hearts by the Classics to Keep, as well as the school’s commitment to leading our scholars to virtue.  I was impressed and excited about the list of works my children would read, which included many of my childhood favorites all the way up to core pieces from college literature and philosophy texts,” she shared.  As a founding family at Northern Oaks, they experienced the infectious joy of teachers sharing their love of learning, and Mrs. Siller was soon drawn in to join the faculty. Beginning first as a long-term substitute and then Apprentice Teacher, she stepped into a Lead teacher role in the middle of her Apprentice year, which led to seven years as a Kindergarten Lead Teacher, and later a Kindergarten Team Lead and Master Teacher. After serving as Dean of Teachers, she took on the new role of Assistant Headmaster, where she focuses on faculty culture.