Robert M. Pennoyer II Appointed Next Head of School

On behalf of the Grace Church School Board of Trustees, we are delighted to announce the appointment of Robert M. Pennoyer II (Robbie), as Grace’s tenth Head of School. After a thorough process, the Search Committee unanimously recommended Robbie to the Board of Trustees, who voted, also unanimously, in support of his appointment to succeed George P. Davison in July 2022. 
Having served as Assistant Head of School and Director of Studies for the past four years, Robbie knows and loves Grace Church School. He has worked closely and collaboratively with faculty to balance continuity and change, tradition and innovation. He 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 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. 

Robbie came to Grace in July 2017 as the Assistant Head of School and Director of Studies. He has since led several teams with a variety of mandates, including redesigning the JK–8 schedule, developing a new diversity statement, and revamping the process for evaluating faculty and supporting their professional growth. He serves on several committees of the Board (e.g., Education, Finance, and the Institutional Culture Committee), and he leads the Education Program Committee, facilitates departmental self-study reviews, and manages faculty professional development. Last summer, working with George Davison and the administration, he was instrumental in developing the school’s plans for reopening safely amid the pandemic. While at Grace, Robbie has taught classes to students in five grades and three divisions.

Robbie is married to Polly Klyce Pennoyer, a bank regulatory lawyer who started her practice at Davis Polk & Wardwell and is now at JPMorgan Chase. They have two children: Victoria, a rising second grader at Brearley, and Cooper, a delightful and industrious two-year-old. 
In accepting this appointment Robbie said:
“Like so many others, I was drawn to Grace because of its values and the people who live them out. I work with exceptional colleagues, whose generosity, know-how, dedication, and skill inspire me daily. Our students do, too. They’re the ones who make credible the bold proposition undergirding Grace’s pedagogy: that stress isn’t the fuel of academic achievement but that joy is; that when teachers can harness students’ natural curiosity, their sense of wonder, and their desire to make the world a better place, then their learning can astonish, delight, and forever shape them.”
“Working at Grace—serving its faculty and staff, its students, and its broader school community—has been a tremendous privilege. I am humbled and honored by the opportunity to continue doing so as the next head of school, building upon the transformational legacy of George Davison’s years at Grace, and I’m grateful to the Search Committee and to the Board for their service to the school, their commitment to its values, and their trust in me. I look forward to working with all the creativity, energy, optimism, and love I can muster to prove myself worthy of that trust and worthy of all who are a part of this extraordinary school community.”

Support from the Community

Numerous members of the Grace community praised Robbie during this process and wrote, unsolicited, to the Search Committee: 

“Robbie has repeatedly demonstrated with both his way of working and his work-product that he has the intellect-skill-experience informed capacity, the resolve, the relationships, the trust, and the grace to lead and model a new era of continued excellence for Grace Church School.” (Grace Parent) 

“Mr. Pennoyer has the talent and the drive to achieve each and every priority of your committee. He will engage this community in the hard work before us. His intelligence, kind heart and indomitable spirit will meet the many challenges of leadership. Mr. Pennoyer's commitment to Grace is steadfast and well known.” (Grace Alumni Parent and former Trustee)

“Parents, students, alumni and especially teachers all respect him: a feat I can’t imagine anyone else pulling off. Having met dozens of school leaders over the years, I feel like Robbie is truly extraordinary. He understands curriculum, mission and people.” (Grace Alumnus)

Our Search Process

Our appointment of Robbie is the culmination of a comprehensive six-month search process. We extend our heartfelt thanks to all members of the community whose participation was essential to a thorough, thoughtful, and inclusive search that affirmed the qualities we identified as essential in our next Head of School: strong leadership skills, integrity, a passion for education and children, the ability to promote and model academic excellence, and a commitment to building a community where every student feels they belong. 
Since the January 2021 announcement of George Davison’s retirement, we have worked closely with our consultants at Carney, Sandoe & Associates and are thankful for their extraordinary work. Our consultant team interviewed faculty, staff, students, parents, alumni and administrators, gathered information through a survey of the entire Grace community and relied on the perspectives of Search Committee members to help craft a position description that attracted over 120 applicants. 
From that initial pool we identified a dynamic and diverse group of 18 outstanding candidates. The Search Committee interviewed ten of these individuals, which resulted in three finalists who together embodied a rich diversity of race, gender, personal background, and professional experience. Each was highly qualified and presented different and inspiring visions for Grace. The finalists each visited the two campuses and met with a broad representation of parent and alumni leadership, departmental and division heads, and the senior administrative team who then provided feedback to the Search Committee. You can read more about the search process here.

Please join us in congratulating Robert M. Pennoyer II on being named Grace’s next Head of School. When Robbie steps into the role in July of 2022, he will be following George P. Davison’s 28-year tenure. In the year ahead, George and Robbie will work together toward a seamless transition, as we continue to build upon Grace’s long history of excellence and strive to live out the high values of our mission.

We wish you a wonderful summer and remain deeply grateful for your continued support of and trust in Grace Church School.
Olivia W. Douglas, Chair, Board of Trustees
Melanie Weston, Chair, Head Search Committee

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 - Faculty, Alumna Class of 1982 and Alumni Parent
Don Waring - Rector of Grace Church, Grace Church School Ex-Officio Trustee and Alumni Parent