Director, Events and Experiences

Now hiring: Director, Events and Experiences

Employment Terms: Full-time, Permanent

Start date: January 2026 onwards

The Director, Events and Experiences, is responsible for creating, implementing, and continuously enhancing a dynamic roster of community events and programs that strengthen engagement and advance UCC’s strategic and fundraising priorities.

With a focus on delivering an elevated guest experience and upholding the highest professional standards in planning, execution, and consistency, the Director leads a team of event managers dedicated to innovation and continuous improvement. Together, they deliver compelling events across a wide range of formats, objectives, audiences, and venues.

The Director serves as a creative partner, proactive collaborator, and adaptable problem-solver. This role requires a highly organized leader and relationship-builder who can foster connections across the UCC community—including employees, parents, Old Boys, donors, and friends.

Key Responsibilities and Tasks

Strategic Event Leadership

• Develop and implement the strategy, standard operating procedures, and annual operational plans for UCC’s events and community programs;
• Maintain broad awareness of institutional priorities, advancement initiatives, communications plans, donor engagement objectives, and sustainability considerations;
• Serve as the creative lead in informing, motivating, and engaging the UCC community through compelling, inclusive, and high-impact events.

Event Creation and Enhancement

• Lead the creation of new events and the enhancement of existing traditions, including:
  • Signature events: Association Day, Founder’s Dinner, Norval Days, Alumni Weekend, Reunion
  • College events: Leaving Class Ceremony, Remembrance Day Ceremony, Branch events
  • Fundraising and donor events: galas, cultural experiences, workshops, lectures
• Provide leadership and oversight of the Advancement Meetings & Event Schedule.

Direct Event Leadership and Management

• Oversee the full lifecycle for selecting high-impact events, including budgeting, logistics, vendor management, evaluation, and reporting;
• Delegate and oversee execution across the team with coaching and quality assurance.

Stakeholder Relations

• Serve as an ambassador for Advancement;
• Manage relationships with senior volunteers;
• Maintain internal and external partnerships.

Leadership, Management and Supervision

• Contribute to Advancement strategic planning;
• Manage and develop a team;
• Mentor team members.

Evaluation of Events and Programs

• Continuously assess programs;
• Monitor peer institutions;
• Develop strategies for participant feedback.

Additional Responsibilities

• Utilize market research to identify community needs;
• Negotiate with suppliers to ensure competitive pricing and sustainability;
• Oversee deliverables and evaluate vendor performance;
• Collaborate on marketing materials;
• Use technology to broaden accessibility.

Job Requirements

Experience, Knowledge and Competencies:

• Postsecondary degree or diploma in event management, marketing, communications, or related field;
• 7+ years of relevant event, marketing, and/or program management experience;
• 5+ years of team management experience;
• Proven experience with trends in event planning and engagement;
• Knowledge of school/College advancement understanding;
• Experience in budgeting and planning.
• Strong demonstrated analytical, problem-solving, and organizational skills;
• Ability to make decisions in fast-paced environments;
• Demonstrated expertise in event logistics;
• Ability to analytically and quantifiably evaluate event effectiveness;
• Ability to gather and interpret feedback;
• Exemplary communication, problem-solving, negotiation and mediation skills;
• Effective team member;
• Invest in personal development and strive to grow professionally.

What We Offer

• Unparalleled opportunities for professional development including workshops, networking sessions, a leadership program, and visiting experts and scholars; Comprehensive medical, dental and vision plans, including health care and lifestyle spending accounts;
• Pension plan, generous vacation time, self-funded sabbaticals, parental leave top-up;
• Significant support for personal and family wellbeing and mental health, including the Employee and Family Assistance Program;
• Paid volunteer time off for involvement in the communities that matter to you;
• Social events for colleagues and their families;
• Collaborative and supportive team members and colleagues;
• Free on-campus parking.

About UCC

Upper Canada College (UCC) is focused on making the world a more just and inclusive place through dialogue and teamwork. With a commitment to equity and fairness, students learn that what makes us different as individuals makes us stronger as a community. A rigorous academic program is supported by accomplished faculty, exceptional co-curricular programming, and state-of-the-art facilities.

The UCC experience is underpinned by five core values: learning, pluralism, service, community, and well-being. Among its strategic goals is UCC’s ambition to become more diverse and inclusive. This is supported by a recognition that no learning community is whole without the inclusion and amplification of multiple voices; UCC is committed to fostering belonging, striving for jus­­tice and peace among all people, and addressing systemic and structural forms of oppression.

UCC is an Equal Opportunity Employer and values diversity, encouraging applications from all qualified individuals including women, Indigenous Peoples, persons with disabilities, 2SLGBTQIA+ and historically marginalized persons. UCC embraces pluralism – celebrating differences, cherishing similarities, and giving voice to multiple perspectives. If you are contacted regarding a UCC opportunity, please advise if you require any accommodations. The successful candidate will need to go through a criminal record check and a vulnerable sector check.

We thank all candidates in advance; however, we will contact only those selected for an interview. All applications must be received by Monday December 19th, 2025.

Gilmore Partners has been retained to conduct this leadership search on behalf of Upper Canada College. Please contact Andrew Stockton at andrew@gilmorepartners.com to forward your resume and letter of intent.

To learn more about UCC, please visit ucc.on.ca and https://careers.ucc.on.ca/