Holiday Retail Lead — Flexible Schedule & Same-Day Pay

Cherry Hill Programs; Annapolis (MD); On-site; USD 26,000 - 28,000; Full time

Benefits offered by this job

Build leadership experience

Flexible scheduling

Same day pay options

Employee Referral Program

Fun, fast-paced environment

Seasonal opportunities beyond

Exclusive holiday perks: Santa visit,

10 photo prints

10 free holiday cards from Shutterfly

Digital Santa message

3 months Pixie Post

Job summary

Cherry Hill Programs is seeking a Seasonal Holiday Retail Assistant Manager at Annapolis Mall to lead a team delivering magical holiday memories, photo operations, and exceptional guest service. You will work with the Local Manager to drive sales, train seasonal staff, and ensure smooth opening-day setup and ongoing operations.

The role emphasizes staff motivation, inventory management, scheduling, and delivering an outstanding photo experience for families during peak season.

Qualifications

• Must be at least 18 years of age.
• Strong communication, organization, time management, and problem-solving skills.
• Must be comfortable in a cash handling/sales transaction position.
• 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.
• Available to work a minimum of 20 hours a week or as needed.
• Ability to lift and carry equipment up to 10-25 pounds and stand for prolonged periods of time.

Responsibilities

• Promote a positive, collaborative environment while upholding company values and policies.
• Support opening-day preparations, including hiring completion, inventory, equipment setup/testing, scheduling, training, and opening/closing procedures.
• Capture photos and help guests choose memorable souvenirs to take home.
• Photography experience not required.
• Resolve customer concerns and service issues to support a positive guest experience.
• Lead by example and reinforce procedures set by senior management.
• Troubleshoot technical issues and elevate to IT or Local Management as needed.
• Assist the Local Manager with inventory, scheduling, training, recruiting, and other administrative tasks.
• Perform other duties as assigned.

Skills

Team leadership

Customer service

Communication

Scheduling

Education

High school diploma or equivalent

Job description

Cherry Hill Programs is seeking a Seasonal Holiday Retail Assistant Manager at Annapolis Mall to lead a team delivering magical holiday memories, photo operations, and exceptional guest service. You will work with the Local Manager to drive sales, train seasonal staff, and ensure smooth opening-day setup and ongoing operations.

The role emphasizes staff motivation, inventory management, scheduling, and delivering an outstanding photo experience for families during peak season.