Director, Major Gifts - US

Company Overview

Who We Are:

Based in Stratford, Ontario, the Stratford Festival is one of the world’s foremost repertory theatre companies. It operates year-round, presenting a season of about a dozen plays each year between the months of April and November, a rich stream of digital content and hundreds of events designed to deepen understanding of the plays. For every person a theatregoer sees on our stages, we have seven people working behind the scenes, some of the world’s most dedicated and experienced arts workers.

The Stratford Festival is committed to ongoing work to support equity, inclusion, anti-racism and anti-oppression in all areas of our work. These areas include play selection, casting, marketing and public relations efforts, education programs, production, design, recruitment of staff and volunteers, and the composition of the Board of Directors.

Why You Should Apply:

• Creative work environment     
• Paid operational shutdown in December, with flexibility of days being used at alternative times during the year
• Group Insurance Benefits
• Employer matched RRSP
• Employee Assistance Program to encourage work-life balance and strong mental health
• Complimentary & discounted ticket offers and events
• Employee discounts on merchandise and event space
• Being a part of the magic of live theatre!

Job Description

The Director of Major Gifts – USA is responsible for leading strategic fundraising initiatives focused on cultivating and securing major gifts from U.S.-based individuals, foundations, and organizations. This role involves managing a robust portfolio of prospects, developing and executing comprehensive cultivation and stewardship plans, and organizing donor engagement activities across the United States to support the theatre’s mission and financial sustainability. 

Reporting to the Vice President of Advancement, the Director of Major Gifts collaborates closely with the Artistic Director, Executive Director, Finance, Marketing, and other departments, as well as with senior volunteers and board members, to advance the organization’s philanthropic goals. This position also oversees administrative systems related to donor tracking and reporting, supports grant and endowment efforts, and contributes to cross-departmental initiatives that align donor engagement with institutional priorities.

Responsibilities: 

• Strategic Fundraising & Program Development
  
  • Collaborate with the Vice President of Advancement, Artistic Director, and Executive Director to develop and execute strategies for major gifts, managing a portfolio of several hundred US-based donors and prospects. 
  • Establish annual and multi-year fundraising goals in coordination with the Advancement Team and develop actionable plans to achieve revenue targets. Monitor and evaluate progress on an on-going basis and adjust strategies as needed.
  • Support US-based fundraising initiatives, including grant requests and endowment fund development.
• Donor Cultivation & Stewardship
  
  • Design and implement comprehensive qualification, cultivation, solicitation, and stewardship plans for major gift prospects, including individuals and foundations. 
  • Prepare customized proposals, presentations, briefing materials, and stewardship reports to support donor engagement.
  • Conduct in-person meetings with donors and prospects, and maintain a visible presence during the performance season in Stratford and at donor events across the US.
• Relationship Management
  
  • Serve as a primary representative for U.S. fundraising, collaborating with Marketing and key volunteers to plan and execute major gift cultivation events in strategic U.S. cities.
  • Build and manage strong relationships with Board members, senior volunteers, and U.S.-based donors to advance prospect development and deepen engagement.
  • Represent Advancement, alongside the VP of Advancement, on the Festival of America (FOA) Board of Directors.
  • Support the VP, Executive Director, and FOA Chair in identifying, recruiting, and stewarding prospective FOA Board members.
  • Identify and maintain a pipeline of potential candidates for the Festival’s Boards—including the Festival of America, Festival of Canada, and the Endowment Foundation—regularly sharing insights and candidate updates with the VP and Executive Director to support Board recruitment and succession planning.
• Collaboration & Reporting
  
  • Collaborate with other departments—such as Marketing, Education, New Play Development, Langham Directors Workshop, Archives, and the Birmingham Conservatory—to align donor strategies with organizational priorities. 
  • Work with the Advancement team to integrate major giving efforts with annual US based major gift membership programs, including the Playwrights Circle and Michigan Members’ weekend.
• Operations & Data Management
  
  • Oversee administrative responsibilities related to donor management, including accurate tracking of inquiries, relationships, and donations using the organization’s database. 
  • Coordinate with Finance to ensure timely processing of donor pledge payments. 
  • Participate in special events in Stratford and other regions to support donor cultivation and stewardship, recognizing that evening and weekend work is often required during the Festival season.
• Other
  
  • Adhere to the Stratford Festival Health & Safety Commitment and Procedures, and ensure that safe work practices and policies are supported and enforced within reporting structure.
  • Perform other duties as assigned

Minimum Qualifications:

• 8 to 10 years of combined post-secondary education and fundraising experience.
• Demonstrated passion for the arts and alignment with the Stratford Festival’s mission.
• Proven track record of securing gifts from individual donors and foundations with a focus on the U.S. market is preferred.
• Strong understanding of fundraising principles, donor cultivation cycles, and philanthropic trends in the U.S. 
• Proficiency in CRM and donor management systems (Tessitura is an asset). 
• Excellent written and verbal communication skills, including proposal writing and donor correspondence. 
• Ability to interpret and prepare financial reports, donor impact statements, and grant documentation. 
• Knowledge of U.S. charitable giving regulations and cross-border fundraising practices. 
• Organizational skills that allow for the successful management of a portfolio of several hundred prospects and donors.
• Imaginative and innovative approaches to the development of new major gift strategies.

Behavioural Competencies:

• Diplomacy: show discretion and tact in dealing with a variety of stakeholders.
• Strategic mindset: consider, anticipate and prepare for various outcomes, situations and challenges; practice global and long-term thinking
• Teamwork: readily work with others towards a shared goal, actively support teammates and recognize everyone’s contributions
• Time Management: efficiently allocate and use time to meet goals and deadlines, prioritize tasks as necessary.

This full-time posting is for an existing vacancy located in Stratford, Ontario. This position requires the candidate to work onsite, with remote available when required. Regular work hours for this position are Monday to Friday, but may require the candidate to work holiday and weekend hours as scheduled.

Job Type: Full-Time

Annual Salary: $76,000 - $125,000

Application Deadline: Open Until Filled