Director of Advancement

Cobb School Montessori | Simsbury, Connecticut

About Cobb School Montessori

Cobb School Montessori is an independent, nonprofit school serving children from toddler through sixth grade in the Farmington Valley. Rooted in authentic Montessori practice, Cobb empowers children to discover their individual and collective potential through independence, academic excellence, compassion, collaboration, and a love of learning.

Our community is grounded in respect, curiosity, and a deep belief in the dignity and potential of every child. We are committed to fostering a culture of belonging and partnership with families, and to preparing children to engage thoughtfully and responsibly in an interconnected world.

Position Overview

The Director of Advancement is responsible for building a strong and sustainable culture of philanthropy at Cobb while stewarding the school’s story with authenticity and care. This is a relationship-driven leadership role that integrates strategic vision with hands-on execution.

Working in close partnership with the Head of School, Board of Trustees, and Parent and Family Group, the Director designs and leads a comprehensive advancement program encompassing annual giving, major gifts, community engagement, strategic communications, and future campaign readiness.

The Director of Advancement is a member of Cobb’s Senior Leadership Team and collaborates closely with the Business Manager, Director of Communications, Director of Admissions, and faculty and staff to advance the mission of the school.

Responsibilities

Annual Fund & Advancement Strategy

• Partner with the Head of School, Business Manager, and Advancement Committee to establish annual and long-term fundraising goals aligned with institutional priorities
• Design and implement a comprehensive advancement plan aligned with the school’s strategic plan
• Lead all aspects of the Annual Fund, including messaging, segmentation, solicitations, stewardship, and performance tracking
• Develop strategies to broaden participation and deepen engagement across all constituencies
• Lead the strategy and execution of signature fundraising initiatives, including Giving Day and Auction

Endowment & Campaign Readiness

• Support feasibility, planning, and early-phase work for a potential endowment campaign
• Serve as primary liaison to external development consultants
• Assist in developing campaign materials, prospect strategies, and donor pipelines
• Strengthen internal systems and culture to support long-term fundraising success

Board & Volunteer Partnership

• Serve as primary liaison to the Board’s Development Committee
• Partner with the Head of School to engage and support trustees in their philanthropic leadership
• Collaborate with the Parent Association to align community engagement with school priorities
• Recruit, support, and steward volunteers for fundraising initiatives and events

Donor Cultivation & Stewardship

• Partner with the Head of School and Board to shape and advance major gift strategy
• Build and sustain authentic relationships with current and prospective donors, including parents, alumni, grandparents, and community members
• Strengthen alumni engagement and foster lifelong connections to the school
• Ensure timely, meaningful acknowledgment and stewardship of all gifts
• Nurture a culture of giving across the community

Data, Systems & Operations

• Oversee all advancement operations, including donor systems, database management, gift processing, and reporting
• Ensure data integrity, accuracy, and effective use of systems to inform strategy
• Manage pledge tracking, acknowledgments, and donor records

Budgeting & Reporting

• Develop and manage the advancement budget in partnership with the Business Manager
• Provide clear, consistent reporting on fundraising progress to the Head of School and Board of Trustees
• Prepare data and insights for the school’s Annual Report

Communications & Storytelling

• Partner with Admissions and Communications to ensure cohesive messaging and storytelling
• Develop and support advancement communications, including appeals, reports, and donor materials 
• Articulate and elevate the school’s mission, impact, and vision through compelling narratives

Qualifications & Skills

We are seeking a mission-aligned professional who brings both relational depth and operational excellence, and who is energized by contributing to a collaborative, purpose-driven school community.

• Bachelor’s degree required; advanced degree or relevant credentials preferred
• Demonstrated experience (3+ years) in advancement, fundraising, or related work within an independent school or mission-driven nonprofit
• Proven ability to cultivate, solicit, and steward donors with authenticity, professionalism, and care
• Exercises a high level of discretion and judgment in managing confidential donor, financial, and institutional information
• Strong interpersonal skills and the ability to build trust with a wide range of constituents, including trustees, families, volunteers, and colleagues
• Skilled communicator and storyteller, with the ability to translate mission and program into compelling, donor-centered messaging
• Experience managing multiple priorities and projects in a dynamic environment
• Proficiency with donor databases/CRMs and a commitment to data integrity and systems management
• Experience preparing for or supporting capital or endowment campaigns preferred

To apply, please submit your cover letter, resume, and three references to [email protected].