Operations Support Specialist

Position Overview

Whimsy Intermodal is seeking an organized, dependable, and detail-oriented Operations Support Specialist to support our day-to-day transportation and administrative operations.

This position will work across multiple areas of the business and will be responsible for ensuring that operational paperwork, shipment documentation, and internal records are complete, accurate, and properly maintained. The ideal candidate is comfortable working in a fast-paced environment, following up with drivers and internal teams, and handling a variety of administrative and operational responsibilities.

This is a broad support role with the opportunity to learn multiple areas of the transportation and logistics business.

Key Responsibilities

• Collect, review, organize, and maintain shipment documentation, including PODs, BOLs, delivery receipts, interchange paperwork, and other transportation documents
• Follow up with drivers, dispatchers, customers, and internal teams to obtain missing or incomplete paperwork
• Verify that documentation is accurate and properly associated with the correct shipment or order
• Upload, scan, file, and organize documents within company systems
• Assist with data entry and maintenance of shipment and operational records
• Identify missing documentation or discrepancies and work with the appropriate team members to resolve them
• Support dispatch, billing, accounting, and operations teams with documentation and administrative needs
• Assist with customer paperwork and document requests
• Maintain organized electronic and physical records
• Help track outstanding items and ensure they are completed in a timely manner
• Assist with reporting, spreadsheets, audits, and other operational projects as needed
• Provide general administrative and operational support across the company
• Take on additional responsibilities as the position and business needs evolve

Qualifications

• Strong attention to detail and organizational skills
• Ability to manage multiple tasks and priorities at the same time
• Strong written and verbal communication skills
• Comfortable following up with employees, drivers, and other departments
• Basic proficiency with Microsoft Excel, Outlook, and other computer-based systems
• Ability to learn new software and internal processes quickly
• Reliable, accountable, and able to work independently
• Previous experience in transportation, logistics, trucking, administrative support, or operations is preferred but not required

Preferred Experience

Experience with any of the following is a plus:

• Trucking, transportation, or logistics operations
• Bills of Lading (BOLs) and Proofs of Delivery (PODs)
• Transportation Management Systems (TMS)
• Document management
• Data entry
• Dispatch or transportation administration
• Billing or accounts receivable support
• Microsoft Excel

What We’re Looking For

We are looking for someone who is proactive and willing to take ownership of their responsibilities. The right person will notice when something is missing, follow up until it is resolved, and help keep our operations organized.

This position is ideal for someone who enjoys being involved in multiple areas of a business rather than performing the same narrow task every day.

About Whimsy Intermodal

Whimsy Intermodal is an asset-based transportation company specializing in intermodal drayage. We operate a growing fleet of company drivers and owner-operators and serve customers throughout the Chicago market and beyond.

As Whimsy continues to grow, this position will play an important role in keeping our operational processes, documentation, and records organized and accurate.

Pay: From $70,000.00 per year

Benefits:

• 401(k)
• 401(k) matching
• Dental insurance
• Health insurance
• Life insurance
• Paid parental leave
• Paid time off
• Parental leave
• Tuition reimbursement
• Vision insurance

Work Location: In person