Bookings Director

The Corp.of Massey Hall & Roy Thomson Hall•Toronto, ON

8d•Hybrid

About The Position

The 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 strong 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.

Requirements

8+ 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.
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.

Nice To Haves

Proficiency with Momentus Enterprise is a strong asset.

Responsibilities

Oversee 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.