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Senior Director, Advancement

Senior Director, Advancement

  • Full Time
  • Stratford, ON
  • Applications have closed.
  • Salary: $150,000-$175,000

Website Stratford Festival

North America’s leading classical repertory theatre

Head and Heart

What makes the Stratford Festival the largest and most popular repertory theatre in North America?

The simple, immediate, and very human connection between actor and audience. In a world tightly filtered by electronics, constrained by screens, and controlled by hidden interests, the Stratford Festival consistently surprises, delights, and challenges.

Four magnificent theatres. The Festival mounts at least a dozen productions annually, in four distinctive venues. With Shakespeare at the foundation of each season’s playbill, it explores every theatrical style and period imaginable, from new works to the Greeks, from comedy to tragedy, from shameless farce to jaw-dropping musical theatre.

Thanks to the unique repertory model, in any single day an audience member can choose from up to eight different productions and from a vast array of Forum offerings. Such rich variety is one reason why Stratford is an annual theatre and holiday destination for thousands from across North America and beyond.

Above all, the Festival’s artists are among the finest there are – and the work of its actors, dancers, musicians, designers, and directors is supported by the unparalleled talent, drive, and creativity of extraordinary craftspeople behind the scenes.

No wonder that the Stratford Festival is one of the most treasured and influential theatre companies anywhere in the world.

The City of Stratford

The city of Stratford got its name in 1835, long before it became associated with Shakespeare or the theatre.

As vibrant as the Festival itself, Stratford offers its 30,000 residents:

– An affordable range of lifestyle options and real estate choices

– Excellent shopping, from distinctive boutiques to big-box convenience

– First-class public elementary and secondary schools, as well as four private schools

– The Stratford campuses of the University of Waterloo and Conestoga College

– The Stratford Chefs School

– A stunning array of top-flight restaurants

– Weekend farmers’ markets

– Passenger train service by VIA Rail

– Direct buses to downtown Toronto (during the Festival season) and Pearson International Airport

– The beautiful Avon River – and of course those iconic swans!

– Stratford Summer Music and SpringWorks Indie Theatre & Arts

– Stratford General Hospital

– A full range of sports facilities

– Thriving local industries in agriculture and auto parts manufacturing

– Two local radio stations and the daily newspaper, The Beacon Herald

National Geographic Traveler calls Stratford “the type of walkable wholesome town Rodgers and Hammerstein might write a musical about.

Senior Director, Advancement

Stratford Festival

Reports to
Executive Director and Artistic Director

Stratford, Ontario

– 2 Major Gift Managers
– Planned Giving Manager
– General Membership Manager
– Playwright’s Circle Manager
– Researcher
– Special Events Manager
– 4 Support Positions

Key Relationships
– Board Chair and Board of Governors
– Chair of the Advancement Committee
– Chairs, other fundraising committees
– Stratford Shakespearean Festival Endowment Foundation
– Executive Director
– Artistic Director
– Stratford Festival Executive Team


The Organization

Embracing a 67-year heritage of tradition and innovation, the Stratford Festival seeks to bring theatre alive for increasingly diverse audiences, pursue new artistic avenues, and expand the scope and reach of work beyond the stage itself. As part of this effort, the theatre also presents The Meighen Forum, a season-long program of events and activities that complement the playbill; conducts an artistic R&D program entitled the Laboratory; and is midway through a ten-year project – unique in North America – to film all of Shakespeare’s plays.

With an annual budget of $65 million, the Festival earns 95% of its revenue through ticket sales, fundraising, and ancillary activities, making it one of the most self-sufficient cultural organizations on the continent.

A registered charity, the Festival has built an $80-million endowment fund to support operating activities, including training, education outreach, play development, and capital projects.

The $100-million Spirit of the Tent campaign supports the construction and operation of the new Tom Patterson Theatre, which will open for the 2020 season. This 600-seat state-of-the-art facility will both affirm and vastly enhance the Festival’s position as a dynamic world leader in the development and production of live theatre.

By attracting the finest talent from Canada and around the world and by providing the conditions and training that enable artists to achieve their most courageous work, the Festival immerses audiences in a theatregoing experience that is innovative, entertaining, and unsurpassed anywhere in the world, one that is deeply relevant to, and reflective of, our lives and communities.

Reaching for the Stars

In 2019, the Festival’s Board approved a strategic plan entitled “Reaching for the Stars.” Articulating the Festival’s aspiration to be the world’s leading destination theatre, drawing a diversity of audiences and artists for theatrical experiences that delight, enrich, and inspire, the plan sets out a series of ambitious targets pertaining to the work, the audiences, and the organization, and provides a foundation for annual plans for the next five years.

The Opportunity

This is a rare chance to advance the financial and reputational strength of one of the most important arts organizations in the English-speaking world. With the successful conclusion of the $100-million Spirit of the Tent campaign in sight and a new strategic plan in hand, the new Senior Director, Advancement will have the rare opportunity to work with the Board and Executive Team in assessing evolving needs and challenges, setting goals, devising appropriate approaches, and developing a new Strategic Advancement Plan.

You will bring a passion for the performing arts to the Stratford Festival’s vibrant senior leadership team, where you will report to and work closely with the Executive Director and Artistic Director. The Senior Director, Advancement will oversee the fundraising plan for the Stratford Festival, including the annual fund, long-term fundraising (endowment), major gifts, special appeals, membership, and major campaigns.

With responsibility for setting fundraising goals and development plans, the Senior Director will work closely with the Board Chair, with the Chair of the Advancement Committee and other fundraising committees, and with the Executive Director and the Artistic Director.

Key Areas of Responsibility

– Participate in strategic and operational planning for the Festival, with an eye to relationship-building and fundraising opportunities.
– Establish, implement, and evaluate short- and long-range departmental objectives, policies, and operating procedures to ensure goals are met or exceeded in all aspects of Festival advancement, including the annual fund, long-term fundraising (endowment), major gifts, and special events.
– In association with the Executive Director, establish the annual fundraising goal and develop a specific plan and budget to attain this objective. Identify, recommend, and implement strategies that can be realistically employed to reach established goals. Assemble measurement criteria for each fundraising team. Report on revenue achievement at Board and Advancement Committee meetings.
– Direct and assist members of the Festival’s Board of Governors and other fundraising volunteers in meeting revenue goals. In association with the Chair of the Advancement Committee, schedule regular meetings of the Committee and staff to ensure alignment and achievement of these goals. Attend related meetings and present reports as required to the Board of Governors, the Finance Committee, the Executive Team, and the Endowment Foundation.
– Support the work of the Nomination Committee of the Board by identifying prospective Board members and helping to cultivate candidates and orient new Board members.
– Spearhead stewardship and cultivation efforts with the Festival’s donors and potential donors. Serve as the primary steward of the Festival’s major donors. Manage the “moves management” matrix and support the Board and staff in building donor relationships.
– Promote a culture of high performance and continuous improvement, develop Advancement staff using a supportive and collaborative approach, and provide direct guidance and supervision in the execution of department activities. The Senior Director will be responsible for staff performance and development goals, establishing priorities, and conducting annual performance reviews.
– Develop and update fundraising policies, including gift acceptance, naming, and acknowledgements, among others, and ensure adherence to these policies. Ensure compliance with the Canada Revenue Agency and Internal Revenue Service in executing fundraising activities.
– In coordination with the Festival’s Administrative Director, pursue government grant opportunities such as the Endowment Incentives Component of the Canada Cultural Investment Fund and others as appropriate.
– Develop fundraising materials for both the promotion and solicitation of fundraising needs. Collaborate with the Marketing department on the development of the annual communication/solicitation plan.
– Co-operate as required with members of the Festival’s management and staff to achieve the Festival’s goals. Attend management meetings of the Festival’s senior staff.
– Represent the Festival in a dignified and professional manner at all donor-related activities.  This includes attending opening night performances, fundraising events, and other Festival functions as required.
– Ensure that all program standards are met or exceeded and that all program opportunities are maximized. Develop procedures with staff to ensure all programs are implemented in a productive and efficient manner. This includes technological advances and upgrades, as well as office procedures. Monitor and evaluate these procedures.
– Perform other duties as assigned.
Candidate Competencies

– Demonstrated passion for the arts and an alignment with the Stratford Festival’s mission, which is to ensure that the Festival is the premier classical theatre destination renowned for both excellence and innovation.
– Exceptional interpersonal and communication skills that foster meaningful relationships with donors and prospects. Experience in making in-person solicitations with prospective donors and proven success in forging relationships with major donors
– Organizational skills that allow for the successful management of a portfolio of several hundred prospects and donors
– Experience with both Canadian and American fundraising models, trends, and innovative techniques. Understanding of differing approaches and attitudes toward giving in each country and of multi-generational approaches to philanthropy
– Strong attention to detail and ability to manage complex events
– Excellent writing and proposal skills
– Imaginative and innovative approaches to the development of new giving opportunities
– Strong financial ability to develop budget and manage expenses
– Excellent staff management skills and team leadership
– Clear understanding of the relationship and synergies between marketing and advancement activities
– Ability to work well with the Executive Director, the Artistic Director, and the Board of Governors
– High professional standards, with an acute attention to detail.

Candidate Qualifications

– Minimum 10 years’ relevant and progressive senior leadership experience with a mature fundraising team within a not-for-profit environment, preferably in the arts
– Extensive experience in managing a complex portfolio of hundreds of prospects at various stages of relationship with an organization
– Experience in working with prospects, donors, and senior volunteers from both Canada and the United States
– Interest in innovative approaches to fundraising that reflect changing practices, preferences, and demographics of diverse prospect spheres
– Proven track record in setting and reaching financial goals
– Strong communication skills – oral and written
– Strong financial acumen
– A practical, calm, and creative problem-solver and strategic thinker, with the flexibility to react nimbly to the unexpected
– Results-oriented personality with a collegial management approach and high level of integrity
– Disciplined, accepting ownership with a hands-on approach
– University degree or equivalent education and experience in a field related to business or marketing. Master’s degree and CFRE preferred

How to Apply

Please submit your application by emailing your cover letter and résumé no later than March 31, 2020, to:

For more information, please contact Cathy Preston at Preston Human Capital Group at 416-871-1300.

The Stratford Festival is an equal-opportunity employer and strongly values diversity, including gender and sexual diversity, within its community. The Festival is committed to reflecting our city’s and country’s diversity. We are pleased to accept applications from under-represented groups and encourage applications from Indigenous persons, youth, new immigrants, and persons with disabilities. We encourage candidates of all backgrounds to apply.

Preston Human Capital Group
2 St Clair Ave W 18th floor
Toronto, Ontario M4V 1L5 Canada

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