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. 

“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)