Logistics and Transportation Manager
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About the Role
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. Responsibilities 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.
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