Logistics and Transportation Manager

Department: Operations

Reports To: Director of Operations

Direct Reports: Hub Supervisors, Coordinators, Dispatchers, and Drivers

Location: Chicago, IL

Status: Full-Time | On-Site (approx. 15% travel)

Position Overview: The Logistics and Transportation Manager. runs last-mile delivery across the Midwest: Chicago, Minneapolis, Milwaukee, and Madison. This new role leads around 250 part-time drivers, develops hub leadership, and launches new markets as the region grows from 2,500–3,000 deliveries a week toward 10,000+. It calls for strong people leadership and a data-driven focus on cost, quality, and on-time performance.

Last-Mile Delivery & Execution: Own last-mile delivery across all Midwest markets, from hub intake to the customer’s door. Match supply with demand and maintain the cold chain on every delivery. Oversee routing and manage delivery partners on performance.

Multi-Site Operations & Standards: Run sites through regular metric reviews, check-ins, and SOP audits. Track leading indicators and keep standards consistent across sites.

Driver Workforce: Recruit, onboard, and retain a large part-time W2 driver team. Fix onboarding drop-off and handle employee relations consistently.

New Market Launches: Launch new Midwest markets over the next 6–12 months. Staff ahead of volume and protect service in existing markets.

Leadership & Culture: Coach supervisors into stronger managers and make hard performance calls. Build a culture of teamwork and partner with Customer Support, Marketing, and Finance.

Systems & Continuous Improvement: Replace spreadsheets with shared dashboards and support a new data platform. Use data to find problems early, fix root causes, and measure results.

Required Skills: High-volume, multi-drop last-mile delivery experience (not primarily line-haul).Experience leading multi-site operations and hourly teams numbering in the hundreds. Proven success hiring and retaining drivers. Strong grasp of delivery unit economics and cost per delivery. Data-driven, with measurable results to show. Experience developing supervisors and managing performance. Clear communicator with high ownership and openness to feedback.

Preferred Skills: Experience launching new markets or sites from a playbook. Cold chain or temperature-controlled delivery experience. Background in large-scale e-commerce, grocery, or food distribution. Experience with delivery management software and building operational dashboards. Experience managing 3PL or gig delivery partners. This is a fully on-site role Sunday to Thursday.