Pricing Analyst - Drayage

Pricing Analyst – Drayage

Chicago, IL (Hybrid) Full-Time Salary 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 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.

This is an individual contributor role designed for someone with hands-on experience pricing drayage 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 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 drayage 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