Director of Advancement

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.

About This Opportunity

We are seeking a mission-aligned advancement professional to help build a strong and sustainable culture of philanthropy at Cobb. This role centers on authentic relationship-building, compelling storytelling, and thoughtful stewardship of the school’s community and resources.

We welcome both experienced and emerging candidates at a range of experience levels. The title and scope of the role will be calibrated to the right person.

What You’ll Do

• Lead the Annual Fund end-to-end: strategy, messaging, solicitation, stewardship, and reporting
• Build and sustain authentic relationships with donors, alumni, trustees, and the broader Cobb community
• Lead signature fundraising initiatives, including Giving Day and the annual Auction
• Serve as primary liaison to the Board’s Development Committee and external development consultants
• Collaborate with the Parent Association to align community engagement with school priorities
• Support early-phase endowment and campaign planning: materials, prospect pipelines, and feasibility work
• Partner with Communications and Admissions on cohesive, mission-driven storytelling and donor materials
• Oversee donor database management, gift processing, budget tracking, and Board reporting

Who You Are

• Mission-aligned — you believe in what Cobb does and want to be part of it
• A natural relationship-builder with warmth, integrity, and strong people skills
• A clear, compelling communicator who can translate mission into stories that move people
• Proactive and self-motivated — you see what needs doing and take ownership
• Comfortable with technology: CRMs, email platforms, data analysis, and digital design tools
• A quick learner with a growth mindset and genuine team-player instincts

Experience & Qualifications

Required Experience:

• Bachelor’s degree
• Experience in relationship-based roles: development, community engagement, nonprofit programming, admissions, communications, events, or similar
• Familiarity with CRM or database tools; comfort learning new platforms quickly
• A strong desire to grow into a full advancement career with mentorship and support

Preferred Experience:

• Advanced degree or CFRE credential a plus
• 3+ years of experience in advancement, development, or fundraising — ideally in an independent school or mission-driven nonprofit
• Demonstrated track record in cultivating, soliciting, and stewarding donors
• Experience with capital or endowment campaigns preferred

We recognize that talent does not always follow a linear path. If you feel strongly aligned with our mission and believe you have what it takes to contribute meaningfully, we encourage you to apply and tell us your story.

Why Cobb

• A genuinely warm, collaborative school culture where people support each other
• A leadership team that values input, flexibility, and professional growth
• Meaningful work — every conversation, event, and gift directly supports children and families
• The opportunity to help shape and grow a development program at an exciting moment in the school’s history

To Apply

Please submit a cover letter and résumé to [email protected]. In your cover letter, we especially welcome a description of why Cobb’s mission resonates with you personally.

Cobb School Montessori is an equal opportunity employer committed to building a diverse and inclusive community.