Winter Events Supervisor

hybrid
Toronto, Ontario, Canada .
contract . October 8, 2025

Description

Position Type: Full time, Contract

Location: 250 Fort York Blvd, Toronto ON

Start Date: November 10, 2025

Length of Position: 4 months

Compensation: $52,000/year (prorated to $17,333 over 4 months)

Deadline to Apply: October 24th at 5pm

Position Summary 

Reporting to the Production Manager and working in close collaboration with the Production team and on-site facilities staff, the Winter Events Supervisor is an integral member of The Bentway team. Primary responsibilities include supporting the administration and implementation of the Bentway’s skating season and third-party event rentals including, but not limited to, managing the Winter staffing calendar, planning for concessions, event coordination, and day-to-day oversight of event assistants. This role will liaise closely with internal and external partners and stakeholders.

About  

The Bentway is a dynamic civic organization dedicated to enhancing urban life through the design and implementation of innovative public spaces, public programming, and site operations. Deeply rooted in Toronto’s urban fabric, The Bentway leads a creative movement to re-imagine the possibilities of the Gardiner Expressway. We believe in the power of art and culture to spark the urban imagination, transform communities and foster vibrant, inclusive cities.   

The Bentway Conservancy is a non-profit organization and registered charity that works closely with the City of Toronto, artists & creatives, and local communities to bring our work to life.  

Responsibilities 

Act as on-site Supervisor during seasonal programming run
Support winter hiring and lead ongoing staff scheduling throughout the season.
Manage vendors to support load-in.
Coordinate signage production and installation with Communications team.
Oversee concessions, including purchasing, staffing and customer service.
Assist in the coordination and delivery of third-party rentals, sponsor activations and internal Bentway programming.
Oversee event assistants, concessions and skate staff during season run.
Serve as a front-line customer service representative for visitors and other members of the public.
Facilitate entry and exit of visitors in accordance with pre-registration/walk-up protocols, as applicable.
Conducting audience counts, weather tracking, and noise monitoring.
Assist with and/or perform first aid, depending on training.
Monitor and record site conditions on an hourly basis, noting weather, attendance and noise.
Open the site or close the site as needed.
Help to maintain order onsite by identifying and addressing hazards and overcrowding, together with Bentway staff.
Recommend changes and/or improvements to equipment, facilities and procedures and report problems to the Facilities Supervisor.
Escalate situations to the Facilities Supervisor, as needed, but definitely in case of severe injury, incidents relating to staff or public safety or if media are involved.
Follow all health & safety protocols established by the employer.
Assorted production duties as needed, including but not limited to: loading, unloading and dismantling of materials; regular lifting of heavy materials; setting up and packing away AV equipment.
Assist with seasonal load-out.
Other duties as assigned.

Qualifications 

Graduate from a post-secondary program in Event Management, Arts Administration, or equivalent years of experience
Experience with scheduling and managing part-time staff
Experience with managing vendors and supervising events
Excellent interpersonal skills, including the ability to work effectively in a team environment  
Confident communicator – ability to communicate with both the public and a wide spectrum of stakeholders 
Evidence of problem solving and the ability to adapt to on-site conditions, and last-minute changes from clients from the clients 
Ability to work flexible hours as needed for event management, including evenings, weekends and holidays 
Current standard level First Aid/CPR-C an asset 
Ability to think creatively, conceive and implement new ideas 
Proficiency with the Microsoft Office Suite, Share Point, Word, Excel, ability to learn and adapt to various digital platforms such as Airtable, Approval Max, DocuSign and more

Applications  

The Bentway is committed to fostering a positive and supportive environment that promotes equity and diversity. We encourage individuals from equity deserving groups to apply, including Indigenous, Black and racialized applicants, persons with disabilities, members of the 2SLGBTQ+ community, and women. 

In accordance with the Ontario Human Rights Code, Accessibility for Ontarians with Disabilities Act, 2005, accommodation will be provided at any point throughout the hiring process, provided the candidate makes their accommodation needs known to The Bentway Conservancy at hello@thebentway.ca.   

We kindly ask that no phone calls or emails are made to staff members. All questions regarding the position must be sent to hello@thebentway.ca.   

Applications sent to the email will not be considered, only apply via the job board.

To Apply   

Apply with a resume and cover letter via The Bentway’s job board. 

Deadline to Apply: October 24 at 5pm

Application Components:  

-Resume (PDF format, no more than three pages)  

-Cover Letter (PDF format, no more than two pages)

The Bentway does not utilize AI to sort applicants, each submission (even the cover letter!) is reviewed by a person.

We thank all applicants for their interest and will endeavour to contact all applicants, whether successful or not.   

Compensation

$52,000.00 per year

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