Vacancy Status: This posting is for a current vacancy on our teamSalary Range: $80k - $90kAbout UsThe Corporation of Massey Hall and Roy Thomson Hall is a registered charity that operates two of Toronto’s most iconic venues: Roy Thomson Hall and Allied Music Centre—home to legendary Massey Hall, TD Music Hall, Allied Music Centre Theatre, Deane Cameron Recording Studio, and more. Guided by a professional management team and volunteer Board of Governors, the Corporation is dedicated to enriching communities through the cultural, social, and economic power of music. The Corporation is actively engaged in Artist Development and Education & Community Engagement initiatives as an investment in the next generation of artists and audiences.We offer a compelling Total Rewards package that includes competitive base pay, eligibility for an annual incentive program, Defined Contribution Pension plan, comprehensive Group Benefits, generous time‑off policies, and opportunities for ongoing professional development.Position OverviewThe Bookings Director is responsible for all rental events taking place in our venues, which comprise the majority of activity in our buildings. Leading a skilled team responsible for these events across our full portfolio of spaces, this role oversees how events move from initial inquiry through confirmation, collaborating interdepartmentally throughout an event’s advance, execution, and close with key customer service touchpoints. The Bookings Director ensures that events are onboarded with care, clarity, and a strong understanding of both client vision and venue potential. Working closely with colleagues across the organization, they guide a team that helps new and returning clients navigate our venues, cultivates long‑term relationships with key partners, and balances strong systems with a commitment to excellent customer service.Reporting to the Director, Programming Group, and working in collaboration with senior leadership, including the President & CEO, the Bookings Director is a visible and engaged leader who models best practices while remaining closely connected to the day‑to‑day work. Drawing on significant industry experience, they support the team in managing a high volume of inquiries, shaping booking activity in alignment with organizational priorities, and ensuring seamless collaboration across departments. Success in this role is reflected in solid rental activity, client retention, efficient administration, and the strength of relationships:



within the team, across the organization, and throughout the wider live music and events community.Key ResponsibilitiesOversee the event calendar across all venues and spaces, ensuring reliable booking records.Lead the sales pipeline for all rental events including triaging, qualifying, and assigning inbound requests.Guide the creation of clear, compelling event estimates that bring client visions to life.Oversee contracts and payment schedules for all rental events.Assume responsibility, along with members of the bookings team, for the portfolio of rental events and client relationships, setting the standard for service and delivery for the bookings team.Provide leadership and support for organizational relationships with key annual and returning clients, including TIFF and the TSO.Support new clients in navigating our venues and processes, collaborating internally to deliver exceptional experiences.Build a collaborative, inclusive, and high‑performing culture within the Bookings team.Strengthen systems, tools, and workflows to improve efficiency, accuracy, and service quality for the bookings department.Lead budgeting and forecasting for the bookings department, projecting rental activity, overseeing activity reporting, and developing new tools for data analysis.Develop benchmarks and ongoing methods to track success, monitor trends, and identify opportunities for growth and improvement.Act as an ambassador for the organization within the arts, music, and business communities, staying current with industry trends.Qualifications8+ years of leadership experience in event planning, live music, concert booking, or related fields, with direct responsibility for teams and outcomes.Bachelor’s degree in arts administration or equivalent combination of education and experience.Experienced people leader with demonstrated strengths in coaching, mentorship, and leading by example while staying actively involved in the work.Strong strategic and critical thinker with sound judgement in complex, fast‑moving environments with competing priorities.Excellent project management,



organization, and planning skills, with a proven ability to set priorities and manage time‑sensitive work.Trusted communicator who builds strong relationships with presenters, promoters, artists, executives, and internal partners.Solid financial leadership experience, including budgeting, forecasting, and using data to guide decisions.Deep experience with booking and calendar databases; proficiency with Momentus Enterprise is a strong asset.Comfortable balancing big‑picture leadership with hands‑on problem solving alongside the team.Demonstrated strength in negotiation, diplomacy, conflict resolution, and people management.Highly developed interpersonal and relationship management skills, rooted in respect and collaboration.A genuine passion for events, the performing arts, and live music specifically.Strong proficiency in Microsoft Office, particularly Excel.Core CompetenciesExecution & AccountabilityLeadership & Team DevelopmentFinancial & Business AcumenCustomer Experience & Relationship ManagementOperational Excellence & Process ManagementCollaboration & Cross-Functional PartnershipNegotiation & Decision MakingCommunication & InfluenceAdaptability & Problem SolvingIndustry Awareness & External EngagementWork ConditionsManual dexterity required to use desktop computer and peripherals.Interacts regularly with internal and external industry colleagues by telephone, email, and in‑person meetings.Comfort working in both office and facility settings, with the ability to conduct walkthroughs across large‑scale, multi‑level venues.Willingness to work occasional evenings and weekends for performances, donor events, and stewardship activities.Travel between venues will be required on an ongoing basis.Additional Information (if applicable)This is a hybrid role based in Toronto with a combination of remote work and on‑site presence at Massey Hall, Roy Thomson Hall, and Allied Music Centre. Some evening and weekend availability will be required depending on event schedules.The Corporation of Massey Hall and Roy Thomson Hall values diversity and is an equal opportunity employer. Applicants requiring accommodation at any stage of the recruitment process should contact the Human Resources Department. The Corporation is committed to providing employment accommodation in accordance with the Ontario Human Rights Code and the Accessibility for Ontarians with Disabilities Act.#J-18808-Ljbffr

📌 Bookings Director - $80,000 - $90,000 A Year (Winnipeg)
🏢 The Corporation of Massey Hall and Roy Thomson Hall
📍 Winnipeg