Position Overview
We are a newly launched distillery with ambitious plans for rapid growth, seeking an experienced Director of Entertainment to lead live music and event programming at our on-site music hall. This is a rare opportunity to join at the ground level and play a key role in shaping the identity, programming strategy, and long-term success of a growing entertainment venue.
As a senior member of the leadership team, the Director of Entertainment will be responsible for booking and programming top touring, regional, and local talent while building strong relationships across the live entertainment industry. This role oversees artist booking, production coordination, talent relations, budgeting, and show profitability, while supervising Production and Artist Relations teams.
This position is ideal for a seasoned live entertainment professional ready to make a significant impact in a high-visibility, growth-oriented environment.
Key Responsibilities
Programming & Booking
- Develop and execute a comprehensive entertainment strategy aligned with ownership goals
- Curate programming across multiple tiers, including national touring acts, regional artists, local talent, themed nights, festivals, and special events
- Book and route a year-round entertainment calendar featuring 100+ annual shows
- Analyze ticket sales, demand, and pacing to optimize programming mix and revenue
Artist & Industry Relations
- Build and maintain strong relationships with artists, agents, promoters, managers, and publicists
- Negotiate artist fees and oversee talent contracts and settlements
- Manage agency and promoter partnerships
Production & Event Execution
- Oversee event logistics, production planning, and show execution
- Supervise the Production Manager, Artist Relations Coordinator, and event staff/contractors
- Ensure rider fulfillment in collaboration with Food & Beverage and Guest Experience teams
- Lead cross-department planning meetings for major shows and festivals
Financial & Business Management
- Develop show budgets, revenue forecasts, and post-show settlements
- Monitor profitability and cost controls for all entertainment offerings
- Support strategic planning for long-term venue growth and brand positioning
Safety, Compliance & Operations
- Ensure all entertainment operations meet safety, licensing, and compliance requirements
- Coordinate with internal teams and external partners to deliver seamless, high-quality events
Required Experience & Qualifications
- 7+ years of experience in venue programming, booking, touring, or festival management
- Strong network of industry relationships with agents, promoters, and production partners
- Experience opening, launching, or repositioning a live music venue
- Familiarity with Canadian content (CanCon) requirements and Western Canadian touring circuits
- Knowledge of live performance licensing requirements and experience working with guilds/unions
- Strong organizational, negotiation, and leadership skills
Why This Role
- Ground-floor leadership opportunity with a fast-growing brand
- Creative ownership over programming and venue identity
- High-impact role with strong visibility and influence
- Collaborative, entrepreneurial environment with long-term growth potential
