Software manager Jobs in Milton, ON

About Us
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 our Local Manager, you'll lead the team responsible for creating magical holiday memories for children and families. You'll oversee daily photo operations, drive sales and service excellence, and ensure every family enjoys a memorable Santa visit, exceptional photo experience, and outstanding guest service from start to finish.

Why You’ll Love Working with Us:

• Build valuable leadership experience developing skills in team leadership, staffing and scheduling, coaching, sales performance, problem-solving, and delivering exceptional guest experiences
• Same day pay options for early access to your paycheck
• Employee Referral Program
• A fun, fast-paced environment where you’ll lead 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:

• Foster a positive, team-focused work environment
• Create schedules and ensure proper staffing coverage
• Recruit, hire, train, and onboard team members
• Oversee daily operations and site performance
• Respond promptly to business calls and emails
• Drive sales, cash handling compliance, and team performance
• Verify and submit daily deposits and financial paperwork
• Coach team members to deliver exceptional guest service
• Build strong relationships with venue partners and vendors
• Partner with host venues to support efficient operations
• Resolve guest concerns and ensure positive experiences
• Manage seasonal setup, breakdown, and equipment security
• Perform additional duties as assigned

What We’re Looking For

• Must Haves: Must be at least 18 years of age Strong communication, organization, time management, and problem-solving skills Ability to lead a team, work independently, and make sound decisions Availability to attend required pre-season training Ability to work a flexible schedule, including evenings, weekends, holidays, and peak retail periods Availability to work approximately 40 hours per week, with additional hours as business needs require Ability to lift and carry equipment up to 10-25 pounds and stand for prolonged periods of time
• Nice to Haves: Previous leadership or management experience in retail, hospitality, customer service, or a similar environment High school diploma or equivalent Ability to use Microsoft Office and other business technology Experience managing teams or operations across multiple locations Demonstrated success driving sales, guest experience, and operational results Experience with scheduling, training, coaching, and developing team members

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.