Director of Entertainment

Type: In-Office Full-Time

About Our Client

Our client is a fast-growing player at the intersection of craft distilling hospitality and live entertainment in Regina SK and they are looking for a Director of Entertainment who would help bring their vision to life.

As the Director of Entertainment you will play a pivotal role in bringing a premier live music and events venue to life. This is a rare opportunity to join at the ground level shaping day-to-day operations building and leading a high-performing team and driving the success of a brand thats just getting started.

*Relocation to Regina Saskatchewan is required*

Key Responsibilities

The Director of Entertainment leads music hall programming artist booking and relationship management with promoters and agency partners. The role also oversees event logistics talent contracts budgeting and profitability for all shows and entertainment offerings while supervising Production and Artist Relations teams.

Your responsibilities will include:

Programming & Artist Booking

• Curate and execute a diverse compelling live entertainment calendar featuring national touring acts regional performers and local talent.
• Develop booking strategies that balance artistic vision audience appeal and financial performance.

Industry Relationships & Partnerships

• Build and maintain strong relationships with booking agencies promoters managers and artist representatives.
• Position the venue as a preferred destination within the live entertainment ecosystem.

Event Operations & Logistics

• Oversee end-to-end event execution including scheduling advancing shows technical requirements and artist hospitality.
• Collaborate closely with production operations marketing and hospitality teams to ensure seamless event delivery.

Financial Management & Profitability

• Develop and manage entertainment budgets negotiate artist contracts and track show-level profitability.
• Analyze performance metrics to optimize programming decisions and maximize revenue opportunities.

Leadership & Team Development

• Lead mentor and develop Production and Artist Relations teams fostering a culture of collaboration accountability and excellence.
• Establish processes standards and best practices that support sustainable growth and operational efficiency.

Qualifications

To succeed in this role candidates should demonstrate the following:

Education & Experience

• Post-secondary education in Music Business Arts Management Hospitality Business or a related field is preferred but not mandatory.
• 7 years of progressive experience in live entertainment venue management artist booking or music programming.

Technical Skills

• Strong understanding of artist contracts booking agreements and entertainment-related financial models.
• Proficiency with event management systems ticketing platforms and budgeting tools; familiarity with production and technical requirements is an asset.

Key Competencies

• Exceptional relationship-building and negotiation skills within the live music and entertainment industry.
• Strategic thinker with a hands-on leadership style and the ability to thrive in an entrepreneurial fast-paced environment.
• Passion for live music culture and creating unforgettable guest experiences.

Apply Today

Quote Job Reference #82361 and submit your resume directly to Iryna Chubynska via email at No cover letter please

About Us

Executrade is one of Western Canadas most comprehensive full-service recruitment firms with over 50 years of expertise in connecting talented professionals with leading organizations.
We are proud to apply principles of diversity equity and inclusion in all our recruitment practices ensuring equal opportunities for all candidates. Our commitment to these values enables us to match organizations with a diverse range of top talent fostering workplace cultures that thrive on innovation collaboration and respect.
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