Pricing Analyst – Drayage & Intermodal Freight

Pricing Analyst – Drayage & Intermodal Freight

Chicago, IL (Hybrid)Full-TimeSalary Range: $75,000 – $100,000

About Cargomatic

Cargomatic is revolutionizing the transportation industry. Founded in 2013, we power local freight through the first and largest digital marketplace for local trucking. Our AI-enabled platform uses real-time data to match shippers with available drivers, creating flexible, on-demand capacity while improving efficiency across the supply chain.

We’ve been recognized as a Built In Best Places to Work, reflecting our people-first culture and commitment to employee growth, collaboration, and impact.

About the Role

We’re looking for a Pricing Analyst to support our commercial organization by developing accurate, competitive, and operationally sound pricing for drayage and intermodal freight opportunities. This role plays a critical part in our bid and RFP process, ensuring pricing reflects real market conditions, internal cost structures, and the operational realities of port- and rail-centric freight.

This is an individual contributor role designed for someone with hands-on experience pricing drayage and/or intermodal logistics, where rates are influenced by terminal constraints, equipment availability, appointment-based workflows, and short-haul network dynamics.

What You’ll Do

Pricing & Market Analysis

• Develop pricing for drayage and intermodal freight using market data, lane performance, and historical trends

• Incorporate port operations, terminal constraints, chassis availability, dwell time, and appointment requirements into pricing assumptions

• Utilize internal cost models and industry tools to price short-haul and port-centric lanes accurately

• Evaluate margin impact and ensure pricing aligns with profitability and network strategy

• Monitor market dynamics, congestion patterns, capacity shifts, and competitor pricing

Bid & RFP Support

• Prepare and review pricing for bids, RFQs, and RFPs with a focus on intermodal and containerized freight

• Ensure pricing submissions meet customer requirements, service expectations, and deadlines

• Partner with Sales, Operations, and other stakeholders to deliver accurate, executable proposals

• Analyze win/loss results and provide recommendations to improve competitiveness and bid strategy

Cross-Functional Collaboration

• Work closely with Sales, Operations, Capacity, and Finance to validate pricing assumptions

• Help determine which freight opportunities align best with our drayage network and operational capabilities

• Support internal teams with pricing insights, scenario analysis, and recommendations

Documentation & Process Improvement

• Maintain pricing documentation, templates, and bid records

• Support continuous improvement of pricing tools, processes, and cost models as the business scales

What We’re Looking For

Required Qualifications

• Experience in pricing, bid management, or analytics within transportation or logistics, with direct exposure to drayage, intermodal, or port-centric freight

• Strong analytical skills and comfort working with data and pricing models

• Proficiency in Excel (modeling, analysis, scenario evaluation)

• Excellent organization, communication, and time-management skills

• Ability to operate effectively in a fast-paced, deadline-driven environment

Preferred Qualifications

• Hands-on experience pricing drayage and/or intermodal containerized freight

• Familiarity with port operations, terminals, chassis providers, and appointment-based workflows

• Exposure to RFP/RFQ processes

• Salesforce or CRM experience

• Experience with freight market tools and rate benchmarking

Benefits & Perks

Cargomatic offers a competitive benefits package designed to support your health, financial security, and overall well-being.

• Medical, dental, and vision coverage with multiple plan options, including HSA-eligible plans

• Company-paid life insurance and short- and long-term disability coverage

• Flexible spending accounts and dependent care savings options

• Employee Assistance Program with confidential counseling, legal, and financial resources

• Wellness programs and benefit advocacy support

Equal Opportunity Employer

Cargomatic is an equal opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all employees.