Director Creative Operations Jobs in Worcester, MA

Position Overview

Pomfret School is making a strategic investment in its future by establishing the inaugural Director of Auxiliary Programs role. This is a rare and exciting opportunity for a visionary, entrepreneurial leader to build a thriving summer and auxiliary ecosystem from the ground up on a stunning 500-acre New England campus. With high autonomy and full support from the school's leadership, the Director will transform strategic vision into operational reality-designing robust summer programs, optimizing world-class facilities for external events, and elevating Pomfret's brand reach. For an ambitious professional who thrives on building mission-aligned programs, fostering team culture, and driving non-tuition revenue, this newly created position offers the chance to leave a lasting legacy at one of the nation's premier independent schools.

About Pomfret

Pomfret School is an independent, coeducational, college preparatory boarding and day school serving 350 students in grades 9 through 12 and postgraduates. Set on a picturesque hilltop in rural Northeastern Connecticut, the school is celebrated for its rigorous academics, robust athletics, and special focus on the arts and experiential learning. Pomfret's academic philosophy is rooted in innovation, project-based learning, and close student-faculty mentorship, preparing graduates to be creative, compassionate, and contributing citizens of the world.

History: Founded in 1894 by William E. Peck, Pomfret School balances a rich historical tradition with an innovative, forward-thinking approach to education.

Location: The 500-acre hilltop campus, originally laid out by renowned landscape architect Frederick Law Olmsted, is located in the charming New England town of Pomfret, Connecticut.

Students: Pomfret enrolls 350 students, featuring a diverse and vibrant community with 21% international students and approximately 22% students of color

Faculty: Pomfret boasts a 6:1 student-to-teacher ratio, with over 50% of the dedicated faculty holding advanced master's or doctoral degrees

Financial Aid: Committed to accessibility, Pomfret awards financial aid to approximately 40% of its student body annually based on demonstrated need.

Strategic Context

In early 2026, Pomfret engaged SPARC (Summer Programs and Auxiliary Revenue Collaborative) to conduct a comprehensive audit of auxiliary programs and develop strategic recommendations. Among the primary findings was a recommendation to invest in dedicated leadership: a full-time Director of Auxiliary Programs to consolidate, coordinate, and grow a cohesive set of auxiliary programs.

This newly created role has been designed in direct response to that recommendation. The Director will be charged with achieving the school's primary strategic priorities for auxiliary programs:

• Generate additional net operating revenue that strengthens Pomfret's long-term financial sustainability.
• Cultivate admissions applicants by engaging youth, especially prospective students, in high-quality experiences on Pomfret's campus.

Position Summary

Pomfret School seeks a visionary, entrepreneurial, and highly organized leader to serve as the inaugural Director of Auxiliary Programming. This critical leadership role is charged with designing, building, and executing a robust, profitable portfolio of year-round and seasonal auxiliary programs.

The primary mandates of this position are twofold:

• Build a thriving summer program ecosystem, including residential and day camps, academic enrichment, arts, and athletic programs.
• Optimize the utilization of Pomfret's world-class facilities, managing all external rentals, events, conferences, and retreats during breaks and off-peak periods.

Created as a direct result of SPARC's strategic audit and backed by Pomfret's Head of School and Chief Financial Officer, this role offers a rare intrapreneurial opportunity to build and grow a new enterprise with the resources, reputation, and long-term commitment of an established independent school.

Job Description

1. Program Development & Summer Camps

• Vision & Strategy: Design, launch, and scale a comprehensive summer program portfolio that leverages Pomfret's unique academic, athletic, and artistic assets (including day camps, overnight sports camps, STEM programs, and creative arts workshops).
• Curriculum & Logistics: Develop engaging, safe, and mission-aligned curricula for youth of varying age groups. Manage all schedules, field trips, daily operations, and transportation.
• Staffing & Leadership: Recruit, hire, train, schedule, and supervise high-quality camp directors, counselors, medical staff, and support personnel. Cultivate a positive, high-energy culture.
• Compliance & Safety: Ensure all youth and summer programs strictly adhere to local, state (State of Connecticut Office of Early Childhood), and federal youth camp licensing laws, health regulations, and industry-standard safety protocols.

2. Facility Rentals & Event Operations

• Sales & Business Development: Actively market Pomfret's campus (including dormitories, dining hall, athletic complexes, performing arts spaces, and outdoor common areas) to external groups such as weddings, athletic leagues, corporate retreats, and educational workshops.
• Client Management: Serve as the primary, high-touch point of contact for all external rental clients from inquiry to post-event wrap-up. Draft rental agreements, collect certificates of insurance (COI), and enforce campus guidelines.
• Internal Coordination: Partner closely with Facilities/Operations, Event Manager, Dining Services, IT, and Athletics to ensure seamless operational support, staffing, and facility turnover. Minimize conflicts with the academic year calendar.

3. Marketing, Finance, & Administration

• Business Planning and Financial Performance: Assume full P&L responsibility for the auxiliary portfolio by developing annual business plans, establishing key performance indicators (KPIs), setting revenue and net operating margin targets, managing operating budgets, and driving the overall financial performance and long-term growth of auxiliary programs.
• Marketing & Recruitment: Collaborate with the Communications and Marketing department to build a strong digital presence for auxiliary programs. Execute targeted campaigns across social media, local directories, and direct mail to drive camper registration and rental inquiries.
• Administrative Oversight: Select and manage software platforms for camp registration, billing, and rental scheduling. Handle contracts, customer service inquiries, and billing/refund management.
• Metrics & Evaluation: Gather feedback, track enrollment data, and deliver detailed financial and operational reports to school leadership annually.

Qualifications and Key Competencies

Education:

• Bachelor's degree required; Master's degree or coursework in business administration, sports management, education, or hospitality is a plus.

Experience:

• Minimum of 5 years of leadership experience in camp administration, event planning, hospitality, or auxiliary program management (preferably in an independent school or higher education setting).
• Demonstrated experience in staff recruitment, training, and supervision.
• Proven track record of generating non-tuition revenue and managing complex budgets.
• Technical Skills: Experience with camp management systems (e.g., CampBrain, Active Network), facility scheduling software, CRM tools, and basic digital marketing platforms.

Interpersonal Skills:

• An entrepreneurial mindset with a proactive, self-starting work ethic.
• Exceptional written and verbal communication skills; ability to build positive relationships with parents, clients, internal departments, and community partners.
• Strong crisis management skills and the ability to remain calm and decisive under pressure.
• Deep alignment with the values, community standards, and educational mission of Pomfret School.

Work Location, Schedule, and Housing

• Year-Round Presence: On-site year-round presence is expected to build internal community relations.
• Summer Requirement: The Director must be physically present on campus during the peak summer programming season (typically mid-June through August) to oversee operations, ensure safety, and manage active programs.
• On-Campus Housing: To support the summer residency requirement, Pomfret School will provide on-campus housing during the summer months (which may be dormitory style accommodations).
• Schedule Flexibility: This position requires significant evening and weekend hours during active rental events and peak summer camp weeks.

Physical Demands

The position requires the ability to move across a large, hilly campus terrain, stand for extended periods, and occasionally lift/move equipment up to 30 lbs.

Timeframe and Start Date

Pomfret is targeting a start date of of October 2026 for this position. The School recognizes that the ideal candidate may have existing professional commitments, including responsibilities related to current summer programs, and is willing to accommodate reasonable flexibility in the start date.

An Invitation To Apply

This is a rare opportunity to build something meaningful, with genuine institutional support, in an environment that takes both mission and financial sustainability seriously. The new Director of Auxiliary Programs will have strong support, a leadership team that is ready to invest, and a community of families who are engaged and enthusiastic.

Pomfret is committed to building a diverse and inclusive community and welcomes candidates of all backgrounds to apply.