Shakespeare in the Ruins is seeking a vibrant, energetic theatre administrator to join us as Managing Director. In this senior leadership role, you’ll partner closely with our Artistic Director to oversee every facet of production, from budgeting, fundraising, and site logistics to volunteer coordination and audience engagement, tapping into the full spectrum of theatre management. You’ll steward SIR’s unique promenade-style performance ecology, championing immersive productions, cultivating community partnerships, and shaping our operational vision. This collaborative opportunity is an important next step in your arts-administration career, where your energy and expertise will help define Winnipeg’s summer theatre experience.

About Shakespeare in the Ruins
Located on Treaty 1 Territory in Winnipeg—consistently ranked among Canada’s most affordable major cities—Shakespeare in the Ruins (SIR) is Manitoba’s only professional theatre company dedicated to producing and revitalizing the works of William Shakespeare and the classical canon. Every spring, we present our signature promenade-style performances under the open prairie sky at the Trappist Monastery Provincial Heritage Park - “The Ruins.” Since our founding in 1993 by some of Winnipeg’s brightest theatre artists, we’ve championed the creation, development, and presentation of Shakespeare-adjacent new work, environmental and site-specific staging, and nurtured the next generation of theatre professionals. Our mission is to connect timeless texts with today’s audiences through inventive staging and community partnerships. Learn more about our history.

To support out-of-town candidates, we offer a modest relocation bonus, so you can make the move to our vibrant, accessible, and affordable arts community.

Our Values
At SIR, we approach Shakespeare and the classical canon with expansion and inclusion, challenging assumptions about what classical theatre can be in the 21st century. We place Shakespeare in conversation with works from the Spanish Golden Age, Latinx and Queer playwrights, and other under-represented cultures whose dramatic traditions stretch back before Shakespeare’s time. We believe our greatest assets are collaboration, creativity, and courage—both onstage and off. We prize cooperation, transparency, and the equitable sharing of our collective gifts. Our casting reflects Manitoba’s rich diversity, and we’re committed to inclusion, decolonization, and access in everything we do. Read more about our commitments and action.

Position Overview

Collaborating with the Artistic Director and reporting to the Board, the Managing Director will:

• Lead Operations & People
• Oversee year-round staff, six seasonal hires, and a large volunteer base
• Manage site logistics for summer productions at Trappist Monastery Provincial Heritage Park and ancillary projects across Winnipeg
• Steward Finances & Fundraising
• Administer our $450K annual budget, deliver monthly financial updates to the Board, and support the development of the 2026–30 Strategic Plan
• Secure $500K+ in grants and $300K+ in earned revenue through ticket sales, rentals, and sponsorships
• Drive Engagement
• Produce 6 seasonal e-newsletters and maintain 15K+ social-media followers
• Cultivate new sponsors, nurture existing donors, and build community partnerships

SIR operates in a co-leadership model: the Managing Director and Artistic Director each bring distinct expertise yet collaborate closely across all operations. The Managing Director works alongside staff, the Board of Directors, external venues, partner organizations, funders, and the public to deliver a summer theatre season and year-round initiatives.

• Commitment: Full-time (40 hours/week); flexibility in hours and days is required to meet production schedules.
• Location: Residency in Winnipeg is required.
• Start Date: October 2025 (exact date to be mutually agreed).
• Compensation & Benefits:
• Salary: $45,000–$50,000 CAD (gross, commensurate with experience)
• Vacation: 3 weeks paid
• Professional Development: Annual allowance

ESSENTIAL QUALIFICATIONS

A. Leadership & Management (2+ years in at least three areas):

• Operational Management
• Project oversight: planning, execution, evaluation of multiple concurrent productions and initiatives
• People Management
• Hiring, coaching, and inspiring staff & volunteers; giving timely performance feedback during peak seasons
• Financial Management
• Budget creation, cash-flow forecasting, financial reporting, and variance analysis
• Fundraising & Development
• Grant research & writing, donor cultivation, sponsorship packages, and private-sector partnerships
• Stakeholder & Board Relations
• Preparing and presenting Board reports; nurturing relationships with funders, partners, and patrons

B. Core Skills & Attributes:

• Passion for classical and site-specific theatre
• Strategic thinking, creative problem-solving, and risk management
• Exceptional written and verbal communication
• Strong time-management and organizational abilities
• Post-secondary education in Arts Management, Theatre Production, Business Administration, or related; or equivalent professional experience
• Proficiency with Microsoft Office suite

Additional Assets

• Familiarity with Canada’s professional performing-arts ecosystem (Manitoba theatre experience is a plus)
• Knowledge of Canadian theatre labour agreements
• Participation in strategic-planning processes or Board service
• Experience in cultural-sector marketing: social media, branding, and asset development (images, video, audio)
• Comfort with QuickBooks, database management, or WordPress updates

KEY RESPONSIBILITIES

Collaborating with the Artistic Director and reporting to the Board, the Managing Director will:

1. Strategic Planning & Governance

• Contribute operational and financial insights to the development, execution, and evaluation of the 2026–30 Strategic Plan
• Prepare and present monthly operational and financial reports to the Board
• Ensure compliance with legal, funding-agency, and governance requirements

2. Operations & Production

• Oversee production schedules, vendor contracts, site permits, insurance, and health & safety protocols at The Ruins and ancillary venues
• Supervise year-round and seasonal staff and volunteers, providing coaching, performance feedback, and a collaborative work culture
• Manage the volunteer program: recruitment, training, scheduling, and recognition
• Archive all company records, correspondence, and reports; maintain the box office and information systems

3. Financial Stewardship & Fundraising

• Align annual business plans and budgets with strategic goals; prepare, monitor, and report on a $450K operating budget
• Lead grant applications, donor stewardship, and sponsorship development; generate reports for government, foundations, and private supporters
• Oversee accounting, payroll, audits, and all financial control protocols; maintain oversight of production costs

4. Communications & Community Engagement

• Shape and execute the company’s marketing and communications strategy: season campaigns, media relations, e-newsletters, and digital outreach
• Serve as public spokesperson at events, in media interviews, and with stakeholder groups
• Plan and host community and donor events (e.g., open rehearsals, receptions) to build audience and fundraising pipelines

5. Culture & Professional Growth

• Foster a safe, inclusive, and transparent workplace that values collaboration, creativity, and courage
• Mentor emerging arts administrators and champion ongoing development through structured performance reviews

APPLICATION PROCESS

Stepping into a co-leadership role is a significant decision, and we’re here to support you. If you have questions about SIR’s structure, culture, or strategic priorities, please reach out to Artistic Director Rodrigo Beilfuss at before applying.

Encouragement to Apply
Even if you feel don’t yet check every box, we want to hear from you—bring your leadership experience, collaborative spirit, and passion for classical theatre, and let us determine how any other skills might be learned on the job.

How to Apply
Submit a single PDF (résumé + cover letter + references) to with “Attention: Managing Director Hiring Committee” in the subject line. Please include:

1. Résumé/CV
2. Cover Letter (max 2 pages) addressing:
• What you would bring to a co-leadership partnership at SIR at this stage of our growth
• The biggest challenges and opportunities you see for SIR (and the wider sector) in our 32nd season
• Your vision for how SIR can meet those challenges and seize those opportunities
3. References: Contact details for at least two professional referees (additional references may be requested later)

Important Details

• Deadline: August 24, 2025 (applications are kept confidential and reviewed on receipt; early interviews may be scheduled)
• Equity & Accessibility: We believe in diversity, equity, and inclusion, and SIR is committed to reflecting the community in which we live, work, and play. We welcome applicants of all backgrounds and abilities—accommodations available upon request.
• Background Check: All offers are contingent on a clear criminal and vulnerable-sector check.

We appreciate the time you invest in your application. Only those selected for an interview will be contacted.