Transportation Planning Manager [Central]

Jitsu; Chicago (IL); On-site; USD 90,000 - 110,000; Full time

Job summary

Jitsu is seeking an Operations Leader to manage the Central and East region last-mile network, overseeing independent drivers, DSPs, and platform drivers to ensure safe, on-time deliveries and cost efficiency.

You will lead a team of Last-Mile Planners and Coordinators, drive weekly allocation, monitor KPIs, and partner with Driver Services, Warehousing, Product, and Call Center teams to optimize processes and driver experience.

Qualifications

• Must analyze operational data to drive improvements.
• Experience leading cross-functional teams in logistics environments.
• Strong communication and decision-making skills.
• Proven ability to manage budgets and optimize costs.

Responsibilities

• Own and manage the Central Region Last-Mile Delivery network, overseeing drivers and DSPs.
• Develop and execute regional short-term, week-over-week delivery allocation plans.
• Ensure efficient daily network operations and address delivery challenges.
• Lead and develop a team of Last-Mile Planners and Coordinators.
• Collaborate with Driver Services, Warehouse Leaders, Product, and Call Center teams.

Skills

Data-driven decision making

Project management

Leadership

Communication

Problem-solving

Safety focus

Industry experience in logistics

Tools

TMS

Last-mile software

Data analytics tools

Job description

About Jitsu

Jitsu is a last-mile delivery service that allows brands to give their customers a consistent delivery experience all the way to the doorstep. Using a proprietary AI-powered technology platform, Jitsu helps its customers deliver on their promise of affordable, reliable, expedited shipping with a 99+% on-time delivery rate. Logistics teams can now provide a differentiated delivery experience at a competitive cost through successful first delivery attempts, fewer claims, coverage in the markets that matter, and upfront pricing with no hidden surcharges. Jitsu operates in urban areas across the U.S., enabling high-volume shippers to exercise control over their end-to-end delivery network. Learn more at gojitsu.com

About the Role

This role will manage the entire regional network of independent contract drivers, Delivery Service Providers (DSPs), and third-party platform drivers, ensuring safe, on-time deliveries, cost efficiency, and seamless operations across the region.

This role will focus heavily on tactical execution, including week-over-week allocation, performance management, and process improvements. In addition to overseeing operations, this role will lead a team of Planners and Coordinators, fostering a high-performance culture and driving continuous innovation in delivery processes.

Operational Leadership

• Own and manage the Central Region Last-Mile Delivery network, overseeing independent contract drivers, DSPs, and third-party platform drivers.
• Develop and execute regional short-term, week-over-week delivery allocation plans to optimize resource utilization and maintain high on-time performance.
• Ensure efficient daily network operations, proactively addressing delivery challenges and maintaining smooth service levels across the region.

Performance Management

• Monitor and drive on-time delivery performance across the East Region, ensuring all drivers and providers meet service level agreements (SLAs).
• Identify opportunities to reduce transportation costs per box while maintaining service quality and customer satisfaction.
• Leverage data analytics to track regional KPIs, analyze trends, and implement operational improvements.

Team Leadership and Development

• Directly lead, mentor, and develop a team of Last-Mile Planners and Coordinators, ensuring clear communication, performance alignment, and professional growth.
• Foster a culture of accountability, collaboration, and continuous improvement within the regional team.
• Provide coaching, performance feedback, and career development opportunities to enhance team effectiveness.

Cross-functional Collaboration

• Partner closely with Driver Services, Warehouse Leaders, Product, and Call Center teams to ensure seamless operations and alignment within the East Region.
• Work with technology teams to optimize and implement solutions that enhance last-mile delivery processes and improve the driver experience.

Safety and Compliance

• Champion safety initiatives across the East Region delivery network, ensuring compliance with all safety regulations and company standards.
• Develop and enforce safety protocols for gig drivers, DSPs, and third-party drivers to mitigate risk and maintain a safe working environment.

Strategic Contributions

• Contribute to long-term planning and strategic initiatives to optimize the carrier mix and network efficiency within the East Region.
• Assist in negotiating agreements with carriers, DSPs, and third-party providers to improve service and drive cost savings.
• Support scaling initiatives for the delivery network, ensuring the region is well-positioned for growth and innovation.

Key Metrics & Focus Areas

• On-time Delivery: Drive best-in-class on-time delivery performance across the East Region.
• Cost Optimization: Continuously improve regional transportation cost efficiency while maintaining service quality.
• Driver Network Quality: Ensure the region has a high-quality, cost-effective, and reliable driver supply.

Required Skills & Qualifications

• Data-Driven Decision Making: Ability to leverage data insights for operational improvements and strategic decision-making.
• Project Management: Proven ability to manage and prioritize operational tasks, projects, and deadlines in a fast-paced environment.
• Leadership: Experience leading remote teams, driving performance, and fostering collaboration.
• Communication: Strong verbal and written communication skills with the ability to work effectively across teams.
• Problem-Solving: Adept at identifying operational challenges, analyzing root causes, and implementing timely solutions.
• Safety Focus: Commitment to enforcing safety protocols and maintaining a safe work environment.
• Industry Experience: 5+ years in logistics, transportation, or supply chain management, with a strong focus on last-mile delivery or gig economy-based networks.

Preferred Skills & Qualifications

• Technology Expertise: Familiarity with transportation management systems (TMS), last-mile delivery software, and data analytics tools.
• Operational Excellence: Strong track record of optimizing delivery processes, reducing costs, and improving service quality.

Physical Requirements

The physical requirements below are representative of what is necessary to successfully perform the essential functions of this position.

• Stand, walk, sit at a desk, work on a computer, climb, kneel, crouch, or crawl.

Travel

This position may require up to 30% of travel time. Work can require regular nights, weekends, or extended hours depending on client needs.

90,000 - 110,000 USD per year (Indianapolis, IN)

90,000 - 110,000 USD per year (Chicago, IL)