Seasonal Holiday Team Lead- Kildonan Place
- Winnipeg, MB
- On-site
- Posted Sep 9, 2026
- 1 position
Opens an external site
- Employment type
- Part-time
- Experience level
- Entry, Junior · 0+ years
- Posting language
- English
- Working hours
- 40 hours per week
Job summary
The Shift Lead is responsible for overseeing daily operations at Santa photo sets, including team leadership, troubleshooting, and ensuring a high-quality guest experience. They will also perform opening and closing duties, manage sales transactions, and assist with photography operations.
Job details
About Cherry Hill Programs Cherry Hill Programs brings the magic to every experience by capturing moments that last a lifetime. In partnership with retail locations, tourist attractions, and destinations across North America, Cherry Hill Programs contributes millions of holiday and souvenir experiences for children and families, year after year. As a Shift Lead, you’ll help create excellent experiences on our Santa photo sets by supporting the team, welcoming families, assisting with photos, and keeping daily operations running smoothly. You’ll bring warmth, energy, and leadership to every shift while helping create a joyful holiday experience guests will remember for years to come. Santa’s season is short and spots fill fast—apply now to lock in your schedule! Why You’ll Love Working with Us: * Build leadership experience by guiding team members, supporting daily operations, troubleshooting on the spot, and helping deliver smooth, memorable guest experiences * Flexible scheduling to fit your lifestyle * Same day pay options for early access to your paycheck * Employee Referral Program * A fun, fast-paced environment where you’ll be part of a team that helps create memorable experiences for families * Opportunities beyond the season — return for future holiday seasons and explore growth opportunities within our souvenir photography division, where available * Exclusive Holiday Perks for You & Your Family: * One free visit with Santa for friends and family, including: * 10 photo prints * 10 free holiday cards from Shutterfly * A personalized digital message from Santa, powered by Portable North Pole * 3 free months of access to Pixie Post, our digital greeting card platform What You’ll Do: * Perform opening and closing duties at assigned venue * Lead by example and reinforce policies and procedures established by Operations Manager/Regional Manager * Troubleshoot technical issues and escalate to IT or Local Management when needed * Assist with training and/or recruiting as needed * Take photos and provide guests with memorable souvenirs to take home * Photography experience not required * Provide excellent guest service throughout the experience * Participate as a team member, ensuring photo operations run smoothly and effectively * Engage in a friendly manner with all guests, staff, and coworkers * Operate POS system and photography equipment * Maintain a safe and clean working environment * All other tasks as assigned What We’re Looking For * Positive attitude and strong work ethic * Team player who can work independently * Good interpersonal and communication skills * Flexibility to work during “peak” retail hours, such as evenings, weekends, and holidays * Ability to process sales transactions and comfortable with cash handling Knowledge, Experience & Skill * Previous retail, service industry, or cashier experience preferred but not required * At least 18 years of age * Ability to lift and carry equipment up to 50 pounds and stand for prolonged periods of time We Work Together to Win Together Our mission is simple: to bring magic to every experience by capturing moments that last a lifetime. We believe that building a diverse team, with a variety of backgrounds and experiences, is the best way to bring our mission to life. Cherry Hill Programs strives to provide a positive work environment that values excellence in safety and quality, free from discrimination and harassment. Every employee plays a part in our Company’s success and makes this a great place to work. Our people are the heart of our organization and the foundation of our success. Driven by our core values of safety, diversity, integrity, and collaboration, we strive to promote a culture that supports and encourages creativity, fairness, and inclusion.
What you’ll do
The Shift Lead is responsible for overseeing daily operations at Santa photo sets, including team leadership, troubleshooting, and ensuring a high-quality guest experience. They will also perform opening and closing duties, manage sales transactions, and assist with photography operations.
Requirements
Candidates must be at least 18 years old and possess a positive attitude with strong interpersonal skills. The role requires the physical ability to lift up to 50 pounds and the flexibility to work during peak retail hours, including evenings and weekends.
Benefits
• Flexible scheduling • Same day pay options • Employee referral program • Free visit with Santa • Photo prints • Free holiday cards • Digital message from Santa • Access to Pixie Post
Listed skills
- Time management · Preferred
- Customer service · Preferred
- Operations Management · Preferred
- interpersonal skills · Preferred
- Leadership · Preferred
- Cash handling · Preferred
- Communication · Preferred
- Conflict Resolution · Preferred
Other relevant skills
Identified from the job description. Confirm important requirements above.
- Leadership
- Team management
- Customer service
- Photography
- POS system operation
- Cash handling
- Technical troubleshooting
- Communication
- Interpersonal skills
- Time management
- Conflict resolution
- Operations management
- Cash Handling
- Technical Issues
- Lifting Ability
- Positivity
- Strong Work Ethic
- Management
- Customer Service
- Creativity
- Sales
- Operations Management
- Operations
- Service Industries
- Troubleshooting (Problem Solving)
- Success Driven
Job areas
- Retail
- Customer Service & Support
- Management & Leadership
- Sales
- Holiday Team Member
- Restaurant / Food Service Supervisor
- Restaurant Managers
- First-Line Supervisors of Food Preparation and Serving Workers
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