EXECUTIVE DIRECTOR, ADVANCEMENT & COMMUNITY ENGAGEMENT

Greenwood College School (Greenwood) is a co-ed / gender inclusive independent day school for students in Grades 7 through 12. Greenwood was founded to inspire students to venture further in order to prepare them for the challenges and experiences of life. Our innovative approach to personalized education allows students to feel positive and engaged each day, while challenging every student to grow.

Greenwood’s professional culture is a highly collaborative and dynamic place to work, where fun and excellence merge together.

Greenwood is seeking an Executive Director, Advancement & Community Engagement with specializations in campaign building and Major Gifts. The successful candidate will oversee the Advancement & Community Engagement (ACE) team, drive our culture of philanthropy and be a key connector to our growing community of parents, past parents, staff, alumni, grandfriends and neighbourhood partners. The school is looking for a skilled fundraiser with extensive experience in stewarding donors and closing major gifts.

Now is the time to build towards Greenwood’s future. The Executive Director, Advancement & Community Engagement will play an integral role in establishing the school’s future by launching a 25th Anniversary campaign focused on growing the school’s endowment, as well as a capital project.

Why Greenwood College School?

Greenwood opened its doors in 2002 to 72 students in Grades 7 and 9. Today, the school numbers 500 students and more than 100 staff. The campus has grown into one of the most advanced facilities among Canadian independent schools. Greenwood’s committed community of parents, alumni, staff and friends have been essential in bringing Greenwood to life and are generous supporters of the school.

Greenwood is an innovative, community-minded school that puts people first. Here you will find engaged professionals who care about the school and work together to make great things happen.

The successful candidate will join our Advancement team at an exciting time in the school’s history, with a new strategic plan in development, significant fundraising and engagement ambitions, and growth opportunities for the school and for staff. Our vision is bold and exciting and the successful candidate will have an opportunity to make an immediate impact.

Reports To: Principal, Head of School

Position Summary

The Executive Director, Advancement & Community Engagement will work closely with their ACE colleagues, volunteers and school staff. They will support all aspects of the Advancement & Community Engagement department in an independent and highly professional manner. Primary responsibilities include:

A. School / Organization Leadership:

• As a leader in the school, support the positive tone of the school
• Overall responsibility for all activities of ACE: Coordinate and execute fundraising, community engagement and ACE communications to internal and external communities
• In collaboration with the Principal, develop strategy for ACE initiatives and approaches
• Build a high-performing ACE team that delivers on raising funds and building relationships
• Oversee the ACE team and ensure each team member is meeting their individual goals and targets to advance the overall ACE program at Greenwood
• Ensure each member stewards their portfolio of prospective and current major gift donors effectively and that community engagement is fulsome
• Be part of the External Relations Team (This team develops and supports strategy implementation and initiatives that are external facing to the school that impact community engagement, fundraising, admissions and communications.)

B. Community Engagement:

• Act as the primary liaison with some external and community partners to the school
• Working with the ACE Team, plan for events and opportunities to celebrate the 25th Anniversary of the school
• Plan, execute and attend Advancement & Community Engagement events

C. Fundraising, Major Gifts, Planned Gifts:

• Build relationships with the school’s top 100 major and planned gift prospects
• Manage a portfolio of prospective and current major gift donors (25-50)
• Campaign: Build, manage and execute the schools next campaign (focused on a capital project & building the endowment)
• Stewardship & Writing: Assist with the content writing for, and preparation of, print and online materials including donor reports, gift agreements, briefing notes and any other materials and documents that assist the ACE team with donor cultivation, stewardship or solicitation
• Planned Gifts: Further build out the planned giving program
• In collaboration with the Principal, develop and operationalize an Advancement Committee to support donor stewardship at the school

D. Advancement Operations and Administration:

• Prepare reports as required for the Advancement Committee, Board of Directors, and Foundation Board
• Ensure all data is recorded in a timely fashion in Raiser’s Edge or other similar Advancement database
• Identify and manage plaquing and naming opportunities

Committees: Foundation Board (Secretary), Roundtable (Parent Association), Advancement Committee, 25th Anniversary Planning Committee, other committees as required

Qualifications and Experience

• University degree or equivalent combination of work experience and education
• CFRE or fundraising designation/certificate considered a strong asset
• Minimum 7-10 years of successful and progressive fund development experience
• Minimum 5-7 years of major gifts experience
• Knowledge of the independent school community and/or higher education sector is an asset
• Demonstrated ability to identify, develop and close gifts at the transformational level +1M
• Experience building and working on a capital campaign
• Experience effectively leading and developing a highly capable team
• Experience working with a Board of Directors and/or fundraising campaign cabinet
• Ideally, experienced with Raiser’s Edge or other similar database system

Skills and Abilities

• Superior interpersonal skills, including the ability to relate effectively with people at all levels both internal and external
• Exceptional writing and presentation skills and the ability to effectively communicate to a diverse constituency, specifically in regard to philanthropy
• Growth mindset with exceptional collaboration skills
• Strong management skills, with the ability to mentor, coach and supervise
• Action-oriented with a strong work ethic
• Ability to develop and manage budgets
• High degree of diplomacy and tact
• Passionate about connecting with people
• Ability to multi-task and adapt well to change
• Creative problem solver with a solutions-oriented approach
• Ability to work before/after hours on occasion for Advancement and school events
• Possesses an appreciation of a small school/small office environment
• Understanding of and alignment to Greenwood’s mission and values

Contact Information

Interested applicants should send their resume to the attention ofHeather Thomas, Principal, Head of School, via email to employment@greenwoodcollege.org. We thank all applicants, however, only those candidates selected for an interview will be contacted.

Greenwood is committed to creating and sustaining a diverse, equitable and inclusive environment for staff, students and families. We aim to embrace individuals whose differences include, but are not limited to: age, ancestry, citizenship, colour, creed, disability, ethnic origin, family status, gender expression, gender identity, marital status, place of origin, race, and sexual orientation. Greenwood is an equal opportunity employer and welcomes applications from all qualified individuals. We embrace pluralism – an ethic of respect that values human diversity. We strive to create a workplace where everyone feels valued, respected and empowered to contribute authentically.

Please advise us if you require any accommodations at any point in the application or interview process.

Please submit both your cover letter and resume in a single pdf file. Files should be in the following name format: initial_lastname_Executive Director-ACE - CV

Application deadline: Friday, September 5, 2025