Constituent Engagement & Annual Giving Officer

12-month, full-time exempt position

Please include a cover letter to be considered

Reporting to the Senior Director of Development in the Advancement Department, the Constituent Engagement and Annual Giving Officer strengthens annual giving programs while deepening alumni engagement with Cheshire Academy. This role requires regular travel (25-30% of time) for donor meetings, alumni events, and engagement programs. Reporting to the Senior Director of Development, the Officer increases philanthropic support by cultivating relationships and building a pipeline of future donors.

The Officer serves as an ambassador for Cheshire Academy's mission to develop character, critical thinking, and confidence in students who become purposeful global citizens. This role is ideal for a collaborative professional passionate about education and community building.

Annual Giving & Donor Relations (50%)

• Develop and execute annual giving strategies to retain and grow donors
• Manage relationships with approximately 100 donors and prospects
• Identify, cultivate, solicit, and steward annual and major gifts to increase retention and upgrade giving levels
• Articulate the Academy's mission to inspire philanthropic investment and engagement 
• Maintain contact reports and use metrics-driven portfolio management

Alumni & Constituent Engagement (40%)

• Collaborate on programs including Reunion, Homecoming, Family Weekend, and "Cheshire Academy: On the Road"
• Create opportunities for alumni involvement through events, communications, and volunteerism
• Leverage digital platforms and social media to expand constituent reach

Strategic Pipeline Development (10%)

• Identify and qualify prospective major gift donors
• Track donor engagement metrics and progress toward fundraising goals
• Utilize CRM systems and data analytics to inform strategies

Education and Experience

• Bachelor's degree required
• 2-4 years of experience in fundraising, alumni relations, or related field
• A passion for independent school education and a deep understanding of the student-to-alumni lifecycle.
• Demonstrated cultural competence and a commitment to fostering an inclusive and supportive school community
• Event planning and virtual platform experience, preferred

Skills and Abilities

• Proven ability to manage donor relationships and achieve goals
• Strong interpersonal and communication skills
• Proficiency with donor management systems (e.g., Raiser's Edge, Salesforce, Almabase)
• Excellent written communication skills
• Self-motivated with strong organizational skills
• Creative thinking with strong project management skills
• Willingness to travel regularly and occasionally during work evenings and weekends; Frequent regional and occasional national travel required, including evenings and weekends.