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


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


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


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


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


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


Bid & RFP Support


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


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


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


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


Cross-Functional Collaboration


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


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


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


Documentation & Process Improvement


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Maintain pricing documentation, templates, and bid records


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


What We’re Looking For
Required Qualifications


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


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Strong analytical skills and comfort working with data and pricing models


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Proficiency in Excel (modeling, analysis, scenario evaluation)


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Excellent organization, communication, and time-management skills


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


Preferred Qualifications


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


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


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Exposure to RFP/RFQ processes


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Salesforce or CRM experience


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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.


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


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


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Flexible spending accounts and dependent care savings options


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


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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.