Seasonal Retail Assistant Manager - Lead Holiday Experience

Cherry Hill Programs; Naples (FL); On-site; USD 35,000 - 52,000; Full time

Benefits offered by this job

Flexible scheduling

Same day pay

Employee Referral Program

Seasonal opportunities

Exclusive holiday perks for you & your

3 free months Pixie Post access

Other holiday perks for family

Job summary

Cherry Hill Programs in Naples, FL is seeking an Assistant Local Manager to help lead the team delivering magical holiday memories through guest service and on-site photo operations. You’ll support daily duties, motivate seasonal staff, and ensure every family leaves with a memorable experience.

The role emphasizes leadership, scheduling, training, and problem-solving, with flexible hours during peak seasons and opportunities to advance within our souvenir photography division.

Qualifications

• Must be at least 18 years old.
• Strong communication, organization, time management and problem-solving skills.
• Comfortable in a cash handling/sales position.
• Lead a team, work independently, and make sound decisions.
• Attend required pre-season training.
• Flexible schedule including evenings, weekends, holidays, and peak retail periods.
• Minimum 20 hours per week.
• Lift/carry equipment up to 10–25 pounds and stand for extended periods.
• Previous leadership or management experience in retail/hospitality/customer service is a plus.
• High school diploma or equivalent.

Responsibilities

• Promote a positive, collaborative environment while upholding company values and policies.
• Assist opening-day prep: hiring, inventory, equipment setup/testing, scheduling, training, opening/closing procedures.
• Capture photos and help guests choose memorable souvenirs.
• Resolve customer concerns to support a positive guest experience.
• Lead by example and reinforce senior-management procedures.
• Troubleshoot technical issues and escalate as needed.
• Assist Local Manager with inventory, scheduling, training, recruiting and admin tasks.
• Perform other duties as assigned.

Skills

Leadership

Team management

Sales skills

Communication

Organization

Problem solving

Cash handling

Training

Scheduling

Flexibility

Education

High school diploma or equivalent

Job description

Cherry Hill Programs in Naples, FL is seeking an Assistant Local Manager to help lead the team delivering magical holiday memories through guest service and on-site photo operations. You’ll support daily duties, motivate seasonal staff, and ensure every family leaves with a memorable experience.

The role emphasizes leadership, scheduling, training, and problem-solving, with flexible hours during peak seasons and opportunities to advance within our souvenir photography division.