Cargomatic

transportation

PricingAnalystDrayage

$75–100k Chicago, Illinois, United States FULL TIME
Market Sentiment
HIGH DEMAND

Neural analysis suggests this role is
optimal for Mid candidates.

The Brief

“Pricing Analyst – Drayage at Cargomatic. Skills: pricing, drayage, bid management, analytics, Excel. 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”

What You'll Achieve.

develop accurate, competitive, and operationally sound pricing for drayage opportunities; ensure pricing reflects real market conditions, internal cost structures, and the operational realities of port; ensure pricing aligns with profitability and network strategy; improve competitiveness and bid strategy

Industry & Context.

transportation
Problems you'll solve

analytical skills; scenario analysis

What They're Looking For.

Must Have

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

Nice to Have

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

What You'll Do.

Develop pricing for drayage using market data

and historical trends

Incorporate port operations

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

and competitor pricing

Prepare and review pricing for bids

and RFPs with a focus on drayage and containerized freight

Ensure pricing submissions meet customer requirements

and other stakeholders to deliver accurate

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

Work closely with Sales

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

Maintain pricing documentation

Support continuous improvement of pricing tools

and cost models as the business scales

How You'll Work.

Team & Collaboration

Partner with Sales, Operations, and other stakeholders to deliver accurate, executable proposals; Work closely with Sales, Operations, Capacity, and Finance to validate pricing assumptions; Support internal teams with pricing insights, scenario analysis, and recommendations

Communication Scope

communication

Full Job Description

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, Operati

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