THE OPPORTUNITY

Upper Canada College (UCC) is seeking an Associate Director, Annual Giving to play a key role in the development and execution of strategies that will strengthen and expand the College’s donor base. This position is critical in supporting UCC’s broader Advancement goals, especially as the institution prepares to celebrate its 200th anniversary in 2029. The Associate Director will focus on three core areas: managing and growing the monthly giving program; developing annual giving campaigns; and overseeing parent-related fundraising initiatives.

Reporting to the Executive Director, Advancement Operations, Associate Director, Annual Giving will work with the broader Advancement team to develop and implement innovative and effective revenue-generation strategies for both annual and monthly giving programs. This will be done with a specific emphasis on engaging UCC’s diverse constituencies, including alumni, parents, past parents, grandparents, and friends. The Associate Director will be responsible for overseeing the planning and execution of initiatives designed to increase participation and contributions, ensuring that these efforts align with the College’s larger fundraising and engagement strategies.

The successful candidate will demonstrate strong project management skills, overseeing multiple fundraising initiatives from inception to execution. This will include creating clear timelines, setting measurable goals, and tracking progress to ensure each project is delivered on time, within budget, and achieves desired outcomes. Effective coordination and integration with key internal teams such as communications, events, and data will be crucial for creating cohesive and compelling donor appeals. The Associate Director will work diligently to monitor trends, evaluate results, and adjust strategies as needed to continuously improve fundraising effectiveness.

A core component of this role will be relationship-building, as the Associate Director will cultivate and strengthen long-term relationships with key donor groups. This involves regular communication with alumni, parents, past parents, grandparents, and friends to foster a deep sense of community and connection with the College. Through regular stewardship and personalized outreach, the new incumbent will nurture relationships that go beyond transactional giving, ensuring donors feel valued and motivated to continue their support. This will involve regular donor engagement through tailored communications, recognition opportunities, and updates on the impact of their gifts.

UCC offers flexible work arrangements based on the needs of the position with expectation of a combination of in-office on our beautiful campus and remote work. There may be some evening and weekend work with this role.

ABOUT UPPER CANADA COLLEGE

Upper Canada College’s mission to deliver transformational learning experiences is supported by expert faculty, cutting-edge facilities, and wide-ranging co-curricular offerings. UCC is an IB Continuum World School with 1,200 students in Senior Kindergarten through Year 12, including 88 boarders from around the world.

Located in central Toronto on 35 acres of green space, Upper Canada College was founded in 1829. Our alumni community of more than 12,500 in 80+ countries include leaders and innovators in politics, finance, arts, athletics, media and beyond. We are proud that approximately 20 per cent of UCC students receive financial assistance from the school’s sector-leading program, with $6 million available annually to Canadian students.

Our Vision: Upper Canada College values each boy and inspires him to be his best self. A UCC experience reflects the pluralism and promise of Canada and identifies the College as a global leader in the education of boys.

Our Mission: Upper Canada College provides transformational learning experiences that foster the development of head, heart, and humanity and inspire each boy to make a lasting and positive impact on his world.

Our Values: Upper Canada College’s values build on our rich history and traditions and serve to inform how we interact with each other and with our world.

Our Values

Learning – Learning about oneself and the world is at the heart of a UCC education. Through a rigorous liberal education and programs of personal development, each boy gains an understanding of himself, strong and wide-ranging skills, and knowledge that prepares him for success and responsible citizenship. We strive for excellence and celebrate accomplishment, valuing learning as a journey and not a destination. At UCC, learning is an ongoing pursuit marked by curiosity, collaboration, persistence, and openness to feedback. As a community, we model a culture of learning and growth.

Pluralism – A UCC experience is about more than just an appreciation of diversity; it is about celebrating differences, cherishing similarities, and giving voice to multiple perspectives. Through an understanding and appreciation of pluralism we create a more inclusive community, and in turn, create a more just society where we work towards the common good.

Community – UCC’s culture is characterized by teamwork, collaboration, mutual respect and a fundamental belief in our Vision and Mission. We appreciate and value each individual, fostering strong and trusting relationships throughout our community. We stand by each other, offering support and care, and we foster in our boys the very best characteristics of brotherhood.

Service – To honour Sir John Colborne’s founding commitment to public purpose, UCC inspires boys to become service-oriented leaders who understand their unique qualities in relationship to others, have humility and empathy, and recognize their ability to positively influence change. At UCC we embrace the opportunity and responsibility to make a difference in our local and global communities.

Wellbeing – To foster individual and institutional well-being, UCC is committed to a learning and working environment that is safe, healthy, meaningful, engaging, and supportive. A UCC education equips each boy with the capabilities to develop the knowledge, self-awareness and strengths of character that enable lifelong resilience and allow him to flourish.

Strategic Directions: Towards 2029

Strategic Directions: Towards 2029 sets the course for our preferred future, one that is driven by our renewed vision to inspire boys to be their best selves and grounded in our mission to provide transformational learning experiences. Our Strategic Directions reaffirm our foundational focus on educating boys in an exceptional day school and boarding environment, delivering a rigorous liberal education through the International Baccalaureate Programme, and ensuring financial accessibility for boys of the highest potential.

Our history of bold and progressive thinking has inspired UCC’s renewed Strategic Directions— developed in extensive collaboration with our community. Three new goal pillars will guide our commitment to these strategic priorities and initiatives. They are Best Self—nurturing the unique combination of head, heart, and humanity in each boy; Flourishing Community—creating a vibrant school that values lifelong engagement; and Bold Future—embracing a culture of courage, striving for excellence, and advancing the common good.

This is a dynamic new agenda for UCC. It bolsters our commitment to deliver innovative teaching practices and learning outcomes, reflects the promise and pluralism of our global society, and supports the wellbeing of our boys, faculty, and staff. Our goals for the future are ambitious and exciting. We look forward to working with all members of the UCC community to achieve them, culminating in the extraordinary milestone of the College’s bicentennial.

For more details, please visit: https://towards2029.ucc.on.ca/

UCC’s Commitment to Pluralism

Education is critical to building an inclusive, just society. When we equip learners to challenge stereotypes, bias, and fear, and to understand their origins — and when we celebrate and support the identities of all in our community and make it safe for them to be themselves — we create true belonging.

To fully realize UCC’s vision to reflect the pluralism and promise of Canada, and to fully live our pluralism value, we’re implementing a multi-year strategy to foster a transformational learning environment where all students, employees and community members feel valued and that they truly belong.

The course we’re charting is grounded in consultation, which has included more than 25 sessions involving close to 400 community members, as well as continuous dialogue, and the creation of a strategic planning committee with representation from across the College. Responding to our community’s needs and to complex global challenges, the strategy aims to remove barriers and biases that impede belonging and inclusion, and to integrate a breadth of voices and experiences.

UCC’s pluralism strategy comprises 56 initiatives and 163 related actions to be implemented over at least the next five years. It addresses eight anti-oppression categories: ableism; anti-racism; antisemitism; homophobia and transphobia; Indigenous reconciliation; anti-Muslim discrimination; sexism; and socio-economic discrimination.

Through our wide-ranging initiatives and actions, we’re paving the way for positive change in seven specific categories across all aspects of College life: curriculum and pedagogy; students, programs, and support; people, organization, and professional development; admission; community; facilities and learning environments; and monitoring and evaluation.

ADDITIONAL INFORMATION

Upper Canada College
UCC History
UCC Leadership
UCC Experience
UCC Strategic Directions

KEY AREAS OF RESPONSIBILITY

Annual Giving and Fundraising Initiatives

Support the overall Advancement goals by creating and executing effective revenue generation strategies for annual giving with a focus on parent giving.
Identifies creative and innovative opportunities in the development or enhancement of existing or new annual and monthly giving campaigns and plans.
Provide strategic direction in the development and implementation of targeted direct-response marketing campaigns designed to achieve growth objectives while maintaining effective cost ratios.
Retain donors by implementing exceptional stewardship practices, leading to renewal, and increased giving.
Manage the execution of all portfolio marketing appeals, including annual giving plans, solicitation calendars, list management and queries, critical paths, creative briefs, copy briefs, instructions to fulfillment houses and setting online giving pages.
Work with, support, and motivate alumni and parent volunteers on class and project appeals, peer to peer fundraising, and other fundraising activities.
Create and monitor optimized donor segmentation and complex plans.
Establish a robust stewardship program for Annual Fund donors, including those who contribute monthly.
Identifies opportunities for cross-promotion between annual giving and major giving, events, and other campaigns.
Respond to donor enquiries in a prompt and timely manner.
Follow up on donor pledges.

Financial and Data Management

Work with Gift Processors to ensure accurate and timely entry of donor/donation data and related information (coding, recognition name, etc.)
Support the distribution of tax receipts and corresponding thank you letters on an ongoing basis.
Ensure timely and accurate acknowledgements of all donations.
Provide ongoing reports on annual fund progress and progress on alumni and parent class giving.
Provide regular reporting to parent annual fund volunteers and class presidents.
Responsible for overseeing the execution of marketing appeals, managing donor data and gift processing, ensuring accurate and timely acknowledgments of donations, and collaborating with various internal stakeholders such as the communications team and finance department.
Accountable for travel and other fundraising related expenses.
Responsible for ensuring the accuracy and confidentiality of donor information.

OTHER

Collaborate with colleagues, and provide general assistance and support as needed, as part of the Advancement Team.
May serve as a mentor to students for International Baccalaureate (IB) continuum projects.

QUALIFICATIONS AND KEY COMPETENCIES

Knowledge of fundraising best practices, and generalist experience in fundraising.
Proven experience in annual giving and/or monthly donor programs, ideally in a nonprofit, educational, independent school, or similar environment.
Proven experience working with individual donors at the entry and mid-level gift levels including knowledge of other revenue streams and digital strategies.
Proven success in building and growing successful relationships with a diverse group of stakeholders in various capacities.
A commitment to excellent donor relations along with knowledge and experience moving prospects through all stages of the donor cycle (cultivation, solicitation, recognition, and stewardship) and towards greater engagement.
Ability to track, analyze, and interpret fundraising data to optimize strategies.
Ability to work in a team-oriented environment, collaborating with other stakeholders within the College and the broader community.
Strong project management skills including managing budgets and financial reports, multiple priorities and deadlines.
Strong writing and verbal communication skills to engage with donors and stakeholders effectively.
Expertise in direct mail and digital marketing strategies.
Familiar with the principles and best practices for engaging and working with volunteers.
Ability to establish rapport, effectively communicate the mission and impact of the organization, and maintain positive and collaborative relationships with diverse individuals.
Ability to assess the effectiveness of existing strategies, identify areas for improvement, and develop innovative approaches to maximize donor engagement and revenue generation.
Ability to troubleshoot challenges, develop creative solutions, and navigate complex situations to ensure the smooth operation of annual and leadership-giving initiatives.
Knowledge of legislation, regulations and guidelines for the management and protection of personal and confidential information, including the Freedom of Information and Protection of Privacy Act.
Proficient with specialized fundraising software (e.g. Raisers’ Edge) and donor databases.

WORKING CONDITIONS

The work involves sitting in meetings and at a computer, with normal levels of walking in the office. The work will also involve standing for longer periods when attending fundraising events. The work may require some lifting and bending when setting up event venues.
Work is performed in an office environment, with occasional attendance at events in other venues.

FOR MORE INFORMATION

KCI Search + Talent has been retained to conduct this search on behalf of Upper Canada College. For more information about this opportunity, please contact Meredith Roberts, Senior Consultant at KCI Search + Talent via email at UCCAG@kcitalent.com.

All inquiries and applications will be held in strict confidence. Interested candidates should send resume and letter of interest to the email address listed above by Friday, January 31, 2025.

Please note that the hiring range for this position is $85,000 – $110,000 per annum, plus a wide range of benefits and perquisites that are available to all UCC employees.

To view the full Position Brief, please visit: www.kcitalent.com.

For more info about working at UCC please visit: https://www.ucc.on.ca/welcome/careers.

UCC is proud to be an Employer Partner of the Canadian Centre for Diversity and Inclusion (CCDI). This partnership provides our team with learning resources and is one part of our journey to embrace pluralism – celebrating differences, cherishing similarities, and giving voice to multiple perspectives.

This position will work in a hybrid model, with three days a week on campus.

A Criminal Records Check and a Vulnerable Sector Check will be required for this position.

Upper Canada College

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Associate Director, Annual Giving