Introducing Robbie Pennoyer

Tenth Head of School Announced

The Penoyer family

After an exhaustive national search, Grace’s Board of Trustees announced the appointment of Robert M. Pennoyer II as Grace’s tenth Head of School in June. In the announcement, Board Chair Olivia Douglas noted, “[Robbie] demonstrates a commitment to a school culture that fosters respect, clear values, belonging, and educational excellence. We are thrilled to have chosen an exceptional leader who is deeply aligned with our core values and ready to move our strategic priorities forward in a manner that advances Grace’s mission.”

About Robbie Pennoyer

Robbie came to Grace in July 2017 as the Assistant Head of School and Director of Studies. He is a lifelong New Yorker, who grew up rooting for the Yankees and singing at the Metropolitan Opera. He is a graduate of Harvard College and Yale Divinity School. A dedicated educator, Robbie served as a teaching fellow at the Shrewsbury School in England, a seventh-grade homeroom teacher and secondary school advisor at St. Bernard’s School and an Upper School admissions officer at Riverdale Country School. He also spent fourteen summers working at Camp Lanakila where he directed the music program, supervised counselors working with the youngest campers and trained staff in teaching and counseling. While at Yale, Robbie studied religion and literature, pastoral ministry, and school leadership. He earned several accolades there, including prizes recognizing the quality of his scholarship, preaching, and character. Robbie was ordained to the priesthood in October 2016 and volunteers as a priest associate at the Church of the Heavenly Rest.


What made you want to serve as Grace’s next head of school?

The people. That’s the short answer. It’s been a privilege to be a part of the Grace community: to serve beside such dedicated teachers whose generosity, know-how, and skill astonish me; to partner with families who care deeply not only about the experience of their own children but also about the wellbeing of the larger school community; and, most of all, to work with young people whose creativity, smarts, and sheer goodness inspire me daily.

Do you have a favorite Grace tradition? 

All-School Chapel. There aren’t many JK–12 schools in New York City that have the space to gather as a full school community or that devote the time to do so. On paper, these chapels shouldn’t work: What program could possibly appeal simultaneously to four-year-olds and to high school seniors? And yet work they do, becoming touchstones of the school year. It doesn’t get much better than listening to voices from all divisions combine in unison to belt out “Amazing Grace.”

Do you have any hobbies?

Visit my office at school or any room in my home, and you’ll realize quickly that I have a book problem. I love to read, and I usually have several books going at once. I ran out of bookshelf space ages ago, so they pile up on my desk, teeter on tabletops, and slump on chairs. Culling them isn’t an option. (Sorry, Marie Kondo, but they spark joy.) I dogear corners of pages I mean to revisit, scribble notes in the margins, and scrawl “TEACH THIS!” across the tops of pages. Living uptown, I get my best reading done on my commute (the bus on my way to school; the subway on my way home). Those happy journeys are not without peril, for the bargain books outside of the Strand and Alabaster Books are as tempting as any Homeric siren.

Tell us something folks may not know about you.

I’ve always enjoyed cooking for family and friends, and while there’s not much that I’ll miss from these many months of pandemic living, the steady routine of family dinners will be an exception. Our tastes vary. Cooper (age 2) is our carnivore and likes a salty pork chop (or two) with applesauce. Victoria (age 7) likes lemony tomato sauce and spaghetti—served separately. My wife, Polly, likes Buffalo tofu salad with blue cheese dressing. Last summer we expanded our quarantine bubble to include my 96-year-old grandmother and kept a log of all the meals we ate together. (Grandma’s favorite: moules-frites with garlic aioli.) Someday I think my family will look back on that meal log as a happy artifact of an uncertain time. For now, they just treat it as a menu.

Robbie speaks with a student during March Madness

Head Search Committee

Melanie Weston – Chair, Head Search Committee, trustee, parent and alumni Parent

MiChelle Carpenter – Dean, Class of 2024

Olivia Douglas – Chair, Board of Trustees, parent and alumni parent

Greg Gushée – Trustee and parent

Yoo Jin Kim – Trustee and parent

Naomi Nwosu-Stewart – Trustee and parent

Kate Patton ’82 – Faculty, alumna, and alumni parent

Don Waring – Rector of Grace Church, Grace Church School ex-officio trustee and alumni parent

Last year, Robbie did an interview with Grace Gazette Editor-in-Chief Ava A. ’22 all about an “unteachable moment” he learned while singing with the Metropolitan Opera.