Holiday Retail Team Lead - Flexible Hours, Growth & Perks

Cherry Hill Programs, Inc; Towson (MD); On-site; USD 23,000 - 25,000; Full time

Benefits offered by this job

One free Santa visit for friends and+

10 photo prints

10 free holiday cards from Shutterfly

Personalized digital Santa message

3 months access to Pixie Post

Same day pay options

Flexible scheduling

Employee Referral Program

Job summary

Cherry Hill Programs is seeking a Seasonal Holiday Retail Assistant Manager at The Shops at Chestnut Hill to oversee daily photo operations, lead a seasonal team, and drive sales excellence during peak holidays.

You’ll collaborate with the Local Manager to deliver memorable Santa visits and exceptional guest service, while managing scheduling, training, and store opening/closing procedures. This role emphasizes leadership, communication, and a customer-focused mindset.

Qualifications

• Must be at least 18 years old.
• 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

Leadership

Communication

Organization

Time management

Problem-solving

Cash handling

Team leadership

Education

High school diploma or equivalent

Job description

Seasonal Holiday Retail Assistant Manager- The Shops at Chestnut Hill

Job Category: Management

Requisition Number: SEASO029763

Apply now

• Posted : September 29, 2026
• Part-Time

Locations

Showing 1 location

The Shops at Chestnut Hill #1425
199 Boylston Street
Chestnut Hill, MA 02467, USA

Description

Pay Range:
Min: $17.00/hr
Max: $18.00/hr

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 Assistant Local Manager , you’ll work alongside the Local Manager to help lead the team responsible for creating magical holiday memories for children and families. You’ll support daily photo operations, help motivate and develop the seasonal team, 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.

Santas’s season is short and spots fill fast- apply now to lock in your schedule!

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
• 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 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:

• 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 escalate 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

What We’re Looking For:

• Must Haves:
• 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
• Nice to Haves:
• Previous leadership or management experience in retail, hospitality, customer service, or a similar environment
• High school diploma or equivalent
• 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.

Equal Opportunity Employer
This employer is required to notify all applicants of their rights pursuant to federal employment laws.For further information, please review the Know Your Rights notice from the Department of Labor.