Seasonal Holiday Retail Manager - Orland Square

Cherry Hill Programs • Orland Park, IL

21d

About The Position

Cherry Hill Programs is hiring a Seasonal Holiday Retail Manager to lead the team responsible for creating holiday memories for children and families at Orland Square. The manager oversees daily photo operations, drives sales and service excellence, and ensures families have a memorable Santa visit, photo experience, and guest-service experience.

The role involves building a positive, team-focused work environment; managing staffing, schedules, and team performance; overseeing site operations; and working with venue partners and vendors. The manager also handles guest concerns, financial paperwork and deposits, seasonal setup and breakdown, and equipment security. The position requires attendance at pre-season training and availability for a flexible schedule, including evenings, weekends, holidays, and peak retail periods. Work is approximately 40 hours per week, with additional hours as business needs require.

Cherry Hill Programs describes its mission as bringing magic to experiences by capturing lasting moments. It emphasizes safety, diversity, integrity, collaboration, inclusion, and a work environment free from discrimination and harassment. The seasonal role may offer opportunities to return in future holiday seasons and explore growth opportunities within the souvenir photography division, where available.

Requirements

• 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 weighing 10–25 pounds and stand for prolonged periods.

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.

Responsibilities

• 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.

Benefits

• Same-day pay options for early access to paycheck.
• Employee Referral Program.
• Opportunities to return for future holiday seasons and explore growth opportunities within the souvenir photography division, where available.
• One free Santa visit for friends and family, including 10 photo prints and 10 free holiday cards from Shutterfly.
• A personalized digital message from Santa, powered by Portable North Pole.
• Three free months of access to Pixie Post, a digital greeting card platform.

What This Job Offers

• Career Level: Manager
• Education Level: No Education Listed