Collections Representative New Chicago, IL
: Job Details :

Join a rapidly growing company revolutionizing the transportation industry! Cargomatic is the #1 technology platform and digital marketplace for powering world-class, local trucking. Local trucking is the lifeblood of every regional economy, and yet this $82 billion industry still relies heavily on phone calls and fax machines. We are using technology to solve complex, real-world problems every day, and giving full transparency to the shipping process.

Cargomatic is transforming the way goods move around metropolitan areas by seamlessly connecting shippers with more than 35,000 professional drivers. It facilitates several thousand shipments per day and cuts shipping-related carbon emissions by eliminating empty miles. We are solving complex, real-world problems for the industry and giving full transparency to the shipping process.

Cargomatic was named to the list of Built In Best Places to Work for 2023, 2024, & 2025 which recognizes the benefits we offer, our people-first culture and commitment to supporting our employees' success, growth and well-being.

Our approach enables our employees – at all levels, and in every role – to thrive in an environment of intellectual curiosity, where people are passionate about what they do and support each other to get the job done. Visit www.cargomatic.com to learn more.

The Collections Specialist is responsible for managing a portfolio of customer accounts to ensure timely payment of outstanding invoices. This role is critical to maintaining a healthy cash flow and involves proactive outreach, reconciliation of account discrepancies, and cross-functional collaboration to resolve billing issues. The ideal candidate is organized, persistent, and customer-focused, with a strong background in collections—ideally within the logistics or transportation industry.

Key Responsibilities

• Manage a portfolio of assigned customer accounts to collect on past-due balances using phone calls, email, and online portals.
• Investigate and resolve payment discrepancies and invoice disputes by collaborating with internal teams (Sales, Operations, Pricing).
• Communicate clearly and professionally with customers to address account issues and drive timely resolution.
• Document all collection activities, communications, and payment arrangements in the Accounts Receivable system.
• Monitor accounts for non-payment, delayed payments, or other anomalies and escalate high-risk issues as needed.
• Send dunning letters and collection notices in line with company policy.
• Negotiate payment plans or settlements within established guidelines and escalate deviations appropriately.
• Maintain accurate customer records including payment terms and contact information.
• Assist with month-end and quarter-end accounts receivable close activities.
• Ensure compliance with applicable collection laws and ethical standards.

Qualifications

• Associate's or Bachelor's degree in Accounting, Finance, or related field preferred.
• 5+ years of experience in collections, accounts receivable, or a similar finance-related role; logistics or transportation industry experience preferred.
• Solid understanding of billing, collections, and accounts receivable workflows.
• Strong communication, negotiation, and interpersonal skills.
• Experience with accounting software (e.g., Command TMS, Cargowise) and CRM tools (e.g., Salesforce) preferred.
• Proficient in Microsoft Office Suite or Google Workspace.
• Ability to work independently and collaboratively in a deadline-driven environment.
• Strong attention to detail and analytical mindset.
• Familiarity with collection laws and regulatory compliance.

Key Performance Indicators (KPIs)

• Daily Collection Productivity
• Days Sales Outstanding (DSO)
• Reduction in Bad Debt Exposure
• Timely Dispute Resolution Rate
• Customer Satisfaction (related to billing inquiries)

The expected salary range for this role is $45,000-70,000. The actual base pay offered will be determined on factors such as experience, skills, training, location, certifications, education, and other factors permitted by law. Decisions will be made on a case-by-case basis. In addition to the base salary, this position may be eligible for performance-based incentives.

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