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 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.
Skills Required
- 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
Cargomatic Compensation & Benefits Highlights
The following summarizes recurring compensation and benefits themes identified from responses generated by popular LLMs to common candidate questions about Cargomatic and has not been reviewed or approved by Cargomatic.
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Healthcare Strength — Healthcare coverage appears robust, with multiple mainstream medical, dental, and vision options and employer‑verified confirmation of comprehensive plans. Benefits materials point to strong plan design details, reinforcing confidence in core health coverage.
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Retirement Support — Retirement offerings include a 401(k) with company match, signaling meaningful long‑term support. Company materials consistently highlight the match as a core component of the package.
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Leave & Time Off Breadth — Flexible/unlimited PTO and paid holidays are prominently featured, indicating broad time‑off offerings on paper. Company materials and listings emphasize flexibility as part of the package.
Cargomatic Insights
What We Do
Trusted by 19 of the top 20 importers, Cargomatic leverages the latest innovations to deliver comprehensive short-haul logistics solutions powered by the industry’s most sophisticated technology platform. The company offers a true one-stop shop—one provider for all U.S. markets managed in one technology platform with a single point of contact for the entire shipment life cycle. Services include LTL, LCL, FTL, FCL, Drayage, Intermodal, White Glove, Final Mile and Storage/Yard Management. Cargomatic’s network of subsidiary-owned assets, owner-operators and fleets provides customers with daily access to more than 35,000 trucks in 50 markets, including the nation’s top 20 ports. At Cargomatic, We Deliver More.
Why Work With Us
At Cargomatic, we tackle logistics challenges with innovative, tech-driven solutions. Our team is empowered to make a real impact in an environment that values curiosity, collaboration and growth. Join us to be part of a forward-thinking culture where passionate people drive meaningful change in how goods move across the globe.
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