Why Not Theatre is looking for an ambitious and creative leader to be our first Director of Development. You are a values-driven strategist and leader, and a generous colleague. You are an excellent communicator with an ability to model and support collaboration both within your team and across functions and levels. Why Not is a fundraising and community-building success story, still at an early stage of its development journey. The new Director of Development will steward this emerging fundraising talent through its next stage, building a strong and sustainable development program, team, and case for support.

Reporting to the Founder and Co-Artistic Director Ravi Jain, and in partnership with the Board of Directors, the Co-Artistic Director and the Executive Director, the Director of Development will work internally to build capacity, systems and programs, and externally to build relationships with major donors and a broad community of partners and supporters. An experienced leader, the new Director will be donor-focused and a strong advocate for Why Not’s vision and mission. A champion of equity and inclusion, they will work to create a diverse and empowered development team, and build collaborative and supportive relationships with the Producing, Finance & Operations, Marketing, and Production teams.

Salary Range: $85,000-95,000, plus a comprehensive benefits package and RRSP matching

Target start date: August-September 2025

This is a hybrid position, with an expectation that the successful candidate works from the Why Not office at least 3 days per week.

Duties and Responsibilities

Leadership and Campaign Strategy

• Build and implement comprehensive development strategies to achieve Why Not’s revenue goals. In partnership with the Founder & Co-Artistic Director, develop Why Not’s culture of philanthropy and integrate donor-centered thinking and the development team into all aspects of the life of the company.
• Innovate and collaborate across teams at Why Not  and within your network to challenge traditional fundraising models, find the right allies and partners for Why Not in the current philanthropic landscape.
• Build a productive and empowered development team, modeling great collaboration and communication.
• Engage Founder & Co-Artistic Director, Board Chair, other Co-Artistic Director, Executive Director, and others in major gift cultivation and stewardship through meetings with donors and prospects, and overseeing meeting preparation (e.g., prospect briefing notes) and follow-up.
• Utilize data and analytics to measure the effectiveness of development strategies, and support data-driven decision-making. Prepare and present reports on fundraising progress, donor engagement, and revenue outcomes.

 

Donor Relationships and Fundraising

• Lead development team in securing five- and six-figure gifts, grants and sponsorships to support Why Not’s artistic projects, programs and services.
• Identify, qualify and cultivate relationships with corporate partners, foundations, and individual donors, ensuring alignment with Why Not’s mission and plans. Develop new customized approaches and build proposals to potential partners with a strong value proposition.
• In partnership with the Founder & Co-Artistic Director and the Executive Director, oversee fundraising content development including proposal and application-writing, finding efficiencies and sharing resources wherever possible.
• Build pipeline of potential funders through partnership opportunities, strategic cultivation, careful research and strategy development, and audience analysis and engagement strategies.
• Design and oversee execution of fundraising, cultivation and stewardship events.
• Provide oversight to Why Not’s development systems including CRM, data management and analysis, fulfilment managing and tracking.
• Share knowledge of best practices around compliance and reporting, including current charitable practices in Canada.

 

Collaborative Culture and Teamwork

• Work with the Founder & Co-Artistic Director and Executive Director to activate and support the Board of Directors in identifying, cultivating, and stewarding major donors.
• Foster an inclusive and collaborative work environment where everyone contributes to the team’s success, setting clear goals and expectations.
• Encourage and embody a hands-on approach, ensuring team members are engaged and motivated, while delegating effectively. Develop a learning and teaching culture, sharing knowledge and best practices with other team members, developing guidelines and training materials to ensure that all needs and expectations are communicated.
• Contribute to Why Not’s strategic plan, annual plans and reports, and Board reports.
• Strengthen the collaborative relationship between development and other Why Not departments to understand funding needs, streamline communication and workflows, and articulate key initiatives to donors.
• Collaborate with ED to build a recognition plan and approach that celebrates the contributions of both private and public sector partners.
• Work with Finance Director, Executive Director and the Founder & Co-AD on developing long-term financial sustainability strategy for Why Not, planning for revenue growth over time.
• Collaborate with the Finance team to ensure accurate revenue forecasting and proper allocation of funds to eligible expenses. Oversee the development and management of the development budget.

 

Qualifications and Competencies

• Progressive fundraising experience including management level experience and a proven track record of success
• Demonstrated experience building and maintaining relationships with major donors
• Demonstrated leadership, decision-making, analytical, and problem-solving skills 
• Demonstrated collaboration and consensus-building skills
• Excellent interpersonal and presentation skills, including both oral and written communications
• Excellent planning, organization, and time-management skills
• High level of integrity and personal commitment to development work. Ability to earn the respect and support of a variety of stakeholders
• Cultural competency to work effectively in a diverse, multicultural workplace
• Preferred experience includes: history of securing major gifts, team/department leadership, and work in the performing arts
• Ability to work occasional evenings and weekends

About Why Not

Why Not Theatre is an international touring company based in Toronto, Canada, operating at the intersection of art, innovation and social change. Rooted in values of community and collaboration, Why Not defies expectations and challenges the status quo, rethinking how stories are told and who gets to tell them. Since its inception, the company has developed and produced over 50 new plays to critical and public acclaim. These works have toured to over 80 cities and garnered over 40 awards and nominations. Why Not is led by Founder and Co-Artistic Director, Ravi Jain, Executive Director, Karen Tisch, and Co-Artistic Director, Miriam Fernandes.

 

Key achievements:

Produced almost 60 innovative, award-winning productions, many of which have toured nationally and internationally. A few examples:

• A Brimful of Asha, created by Ravi Jain with his mother, relays the story of his parents trying to arrange his marriage; premiered at Tarragon Theatre in 2012, the play went on to tour nationally and internationally for over a decade 
• Like Mother, Like Daughter, a show featuring real-life mother-daughter pairs, was produced with Complicite (UK) in 2014 and performed in the UK, Canada, Ireland, Israel, and India 
• Prince Hamlet, a groundbreaking ASL-English production, premiered at The Theatre Centre in 2017, was remounted at Canadian Stage, and later toured across the United States and to Quebec City
• What You Won’t Do For Love, featuring renowned environmentalist David Suzuki opened the Luminato Festival in 2022, and was presented in 2024 as part of Why Not’s first ever signature fundraising event, Why Not Fall in Love with the Planet?, alongside a fireside chat with David Suzuki and now-Prime Minister Mark Carney 
• Mahabharata, Why Not’s spectacular two-part, six-hour retelling of the ancient Indian epic, premiered at the Shaw Festival in 2023 and is currently touring to Banff, Australia, Toronto, Ottawa, and New York City. Eight years in the making, Mahabharata made history as the first POC-directed and authored Canadian production to appear on the Barbican London stage, where the show drew record attendance for a touring production
• Had three plays, Brimful of Asha, What You Won’t For Do For Love and Mahabharata,  published by Coach House Books.

Developed innovative sector-wide programs to support the development of independent artists’ work and the careers of BIPOC artists, including:

• SHARE, a program offering wrap-around support to independent theatre companies and collectives to produce and tour their own work; 1S1, a deaf-led theatre company joined the SHARE platform in 2020
• RISER, a collaborative producing platform launched in 2014 with new works by four emerging artists and expanded nationally to Edmonton and Regina in 2022
• ThisGen Fellowship, a unique national training and mentorship program for BIPOC women and non-binary theatre artists initiated in 2020, with 40 alumni to date
• Space Project, a program providing independent artists access to affordable rehearsal space by partnering with the real estate sector to animate underutilized spaces; piloted in 2019 and expanded into a movement via the National Meanwhile Space Network

Submit your materials here by Tuesday, June 24, 2025.

If you have questions or require accommodations to the application process, please reach out to contact@whynot.theatre.

As a company that values diversity of backgrounds, cultures, and perspectives in its team, Why Not Theatre actively encourages applications from people who identify as Black, Indigenous, People of Colour, Deaf, disabled and 2SLGBTQ+ and highly encourages candidates to self-identify when applying.  The company will endeavour to meet any accessibility requests from candidates taking part in all aspects of the selection process.

Why Not is grateful for everyone’s interest, but only those selected for interviews will be contacted.