Upper School Executive Assistant + Project Manager

Riverdale Country School, a Pre-K through Grade 12 independent all-gender school in New York City, is dedicated to inspiring students to live meaningful and purpose-driven lives. The school achieves this by fostering a culture of academic excellence, critical thinking, and curiosity, supported by a diverse and inclusive community. Riverdale emphasizes both high challenge and high support in its approach to education, encouraging students to engage deeply in interdisciplinary learning, research, and experiential education, both inside and outside the classroom and beyond our campuses. This holistic approach aims to develop well-rounded individuals who are prepared to make a positive impact on the world.
At Riverdale, we strive to reflect the diversity of the New York metropolitan area in our students, faculty, and staff. We believe that a diverse and inclusive community enriches the educational experience and is integral to our mission. With a student body of approximately 1,300 students from 117 different zip codes, Riverdale is a vibrant community where 48% of our students identify as students of color. 
We seek to employ educators and leaders who bring a student-centered approach, passion for their work, a commitment to DEIB, and a desire to contribute to the growth and development of our entire school community.
Job Summary
The Executive Assistant to the Upper School leadership team serves as a key representative of the team, fostering strong relationships and facilitating effective communication across the Upper School division to ensure alignment with divisional priorities and the broader mission of Riverdale. In addition to providing high-level administrative support to the divisional leadership team - the Upper School Head, Assistant Head, and grade-level deans, this position serves as a central point of coordination for Upper School leadership operations. The Executive Assistant acts as a trusted thought partner to the Head and Assistant Head of Upper School, helping to prioritize initiatives, streamline communication, and ensure follow-through on divisional goals. This role also supports the work of the Upper School Grade-Level Deans, coordinating calendars, managing key student-facing operational systems, and ensuring consistency across divisional programming and events.

Administrative Leadership

• Partner with the divisional leadership team to prioritize initiatives, requests, and meeting invitations by assessing urgency, alignment with divisional goals, and potential impact.
• Manage a complex and dynamic calendar for the Head of Upper School, Assistant Head, and Grade-Level Deans.
• Screen and triage communications with sound judgment and discretion.
• Provide rapid-response support during time-sensitive or high-pressure situations, helping coordinate logistics and communication.
• Recommend and implement office procedures and systems that increase efficiency and clarity.
• Create and maintain a joyful space in the Upper School office, welcoming students, families, faculty, and the broader Riverdale community

Divisional Experiences + Special Projects

• Partner with Development, Communications, Athletics, and Special Events teams to ensure smooth execution of critical Upper School events and programs.
• Coordinate logistics and provide operational support for major Upper School events, including Experience Riverdale Day, Graduation, grade-level programs, travel programs, and leadership gatherings.  As needed, manage space reservations, vendors, materials preparation, and day-of logistics.
• Support Grade-Level Deans in managing parent-teacher conferences, grade-level programming, and student-facing systems.
• Assist in planning and execution of divisional retreats, faculty meetings, and all-school gatherings.

Operational Management

• Prepare and track confidential documents related to Upper School personnel processes in coordination with Human Resources and the Business Office.  When required, ensure documents are reviewed, signed, and archived in accordance with school policy.
• Liaise with vendors to procure supplies and resolve service needs efficiently
• Book travel and accommodations for divisional leadership team with attention to detail and cost-effectiveness
• Supervise the maintenance, supplies, and space requirements of the Upper School office, and both deans offices
• Track divisional budgets, reconcile credit card expenses, and monitor purchasing workflows.
• Maintain organized digital filing systems and records aligned with school policy.
• Maintain records and documents relevant to accreditation or divisional review processes.
• Perform other duties as assigned in support of Upper School operations.

Technical & Digital Literacy

• Develop and manage digital systems for electronic record-keeping and document storage
• Utilize relational databases to generate reports (e.g., attendance, grades)
• Use Google Workspace (Docs, Sheets, Calendar, Gmail) to support daily operations and collaboration

Required Experience

• Bachelor’s degree or equivalent professional experience (degree in Business, Administration, or related field preferred).
• 5-7+ years of experience in an executive assistant or senior-level administrative role.
• Demonstrated experience managing complex executive calendars and supporting senior leadership.
• Proven ability to handle confidential information with discretion and sound judgment.
• Exceptional organizational and time-management skills, with the ability to manage multiple priorities and follow through independently.
• High attention to detail and operational accuracy.
• Excellent written, verbal, and interpersonal communication skills, including the ability to work respectfully and effectively with students, families, faculty, and colleagues.
• Proficiency in Google Workspace, word processing applications, and digital filing systems.
• Comfort working with school data systems and relational databases.
• Eagerness to learn and adapt to emerging technologies and systems.
• Positive, collaborative approach and a genuine commitment to supporting a school community.

Core Competencies

• Professionalism and discretion in all interactions
• Sound judgment and ability to anticipate needs
• Highly developed attention to detail and operational precision
• Initiative and systems-thinking mindset
• Flexibility and composure under pressure
• Collaborative approach to working with diverse stakeholders
• Strong relational intelligence when working with students and families
• A sense of humor balanced with seriousness of purpose

To apply for this position, please click on the red “Apply for this Job” button. Please submit a resume and cover letter.  If there are pronouns we should use in potential future communications, we invite you to share that information with us.  For information about this position and all open positions, please visit the Careers page of Riverdale’s website.
Benefits of Full Time Work at Riverdale Country School
Working at Riverdale Country School is a purposeful and meaningful career choice that comes with many benefits including:  
Transportation: Shuttle service is available to/from the 242nd St / Broadway subway station. Limited stops are also available near transit hubs in Manhattan including the Metro North Harlem Station and subway lines – 1, 2, 3, 4, 5, 6, N, Q, R, A, B, C, and D. If there is need in the community, we can also run a shuttle from the Henry Hudson Parkway / 246th St bus stop which connects to the #7, #10, and Express Buses to/from Manhattan.
Professional Development: A generous professional-development budget provides for conferences, skills training, and onsite training in areas such as mindfulness, coaching, and diversity, equity, inclusion, and belonging.
Grants and Stipends: All employees are eligible for Frankel Fellow grants, known as “passion grants,” which pay for enrichment activities. More than 120 grants have been made to faculty and staff since the program started in 2014. Stipends are available for coaching, affinity group facilitation, advising clubs with significant out-of-school time, and chaperoning trips (including global trips!).
Sabbatical:  Full time teaching faculty are eligible for a sabbatical after 10 years of employment.  
Health Benefits: Riverdale offers and subsidizes health, dental, and vision insurance.  In addition, the school offers a flexible spending account through which employees can use pre-tax dollars to pay for health-related expenses.  
Retirement:  Employees are eligible to join our Defined Contribution retirement plan through TIAA.  The school contributes 7% of an employee's annual salary to their retirement account.  
Vacation:  Riverdale Country School has a generous time-off policy for staff in addition to vacations afforded by the school calendar.