Customer Experience Operations Trainee

Job Title: Customer Experience Operations Trainee

Division: Customer Experience

Classification: Non-Exempt

Reports To: Customer Experience Manager

Supervises: No 

Location: Cheshire, CT 

Date: April 2026

Summary: This 18-month entry-level rotational trainee position provides broad exposure to customer experience, order management, logistics, and invoicing operations within the Customer Experience department. The role supports daily workflows by handling routine order assistance and centralized billing tasks, enabling Customer Experience Specialists to focus on sales collaboration and proactive customer relationship management. The trainee will participate in structured rotations and training to build foundational knowledge and skills for future opportunities in operations or customer experience roles.

Essential Job Duties & Responsibilities:

Customer Support & Order Assistance

• Assist with entering and updating customer orders under supervision.
• Help respond to customer inquiries via phone and email using friendly, professional communication.
• Learn to communicate order status, delivery updates, pricing, inventory, and product details.
• Provide backup support to the Customer Experience team during peak periods or team absences to maintain service levels. 
• Identify routine issues and escalate more complex matters to senior team members for resolution.

Invoicing & Billing Support 

• Assist with preparing customer invoices and learning core billing processes.
• Review basic service estimates with guidance to ensure accuracy before invoicing.
• Request, collect, and organize necessary paperwork from freight carriers, service providers, and internal teams.
• Help maintain complete and accurate digital records and attach documentation to orders.
• Work closely with Accounting to resolve simple discrepancies and escalate complex issues.
• Support centralized billing workflows to reduce routine invoicing tasks for the broader CX team.

Systems & Recordkeeping

• Enter and maintain accurate customer and order data in CRM/ERP systems.
• Learn to generate basic reports to track order progress, invoicing accuracy, and documentation completeness.
• Maintain clear and organized digital records across rotations.

Team Collaboration & Rotational Exposure

• Work closely with Customer Experience, Accounting, Logistics, Sales, Product, Credit, and other teams to support daily workflows.
• Participate in rotations, training sessions, and shadowing to build product, billing, system, and supply chain knowledge.
• Provide feedback on processes and suggest improvements as you learn.
• Help ensure smooth transitions and backfills in Customer Experience during team promotions or changes.

Knowledge, Skills, and Abilities:

• High school diploma required; recent college graduate preferred or 1–2 years of relevant experience. 
• Strong communication skills, both written and verbal. 
• Basic computer skills and comfort learning new systems (CRM, ERP, billing tools, Microsoft Office). 
• Strong attention to detail and willingness to learn. 
• Positive attitude, curiosity, and commitment to delivering great service. 
• Ability to adapt to changing assignments across departments.

Physical Demands and Work Environment:

• Office work environment (Monday-Friday).
• Ability to remain in stationary position, sit or stand, at a computer workstation for extended periods.

This is not necessarily an exhaustive list of all responsibilities, requirements, or working conditions associated with this job. Osterman reserves the right to make changes to the above job description whenever necessary.