Regional Last Mile & Delivery Operations Manager (Chicago)

About the Role

This is a hands-on regional leadership role responsible for the performance and scalability of last-mile delivery operations across multiple sites. You will oversee delivery stations and hubs, partner with DSPs and transportation providers, and drive improvements across service quality, productivity, capacity, cost efficiency, and peak-season execution.

We are looking for someone who has directly owned last-mile operations — whether at the station, hub, multi-site, or regional level — and understands how to build reliable operations in a fast-moving delivery environment.

What You'll Do

• Lead end-to-end last-mile delivery operations across an assigned region, with ownership of service performance, delivery quality, productivity, cost efficiency, and execution.
• Oversee multiple delivery stations, hubs, warehouses, or operational sites and ensure consistent day-to-day performance.
• Manage operational relationships with DSPs, delivery contractors, and transportation partners, including capacity planning, onboarding, performance improvement, and service quality.
• Partner with site leaders to identify operational gaps, improve execution, and standardize scalable processes.
• Lead planning and execution for peak periods, changing business volumes, and network growth.
• Manage operating budgets and drive improvements in productivity, capacity utilization, and cost per package.
• Use operational KPIs and data to identify trends and drive measurable improvements.
• Build and develop regional operations teams, including frontline leaders and site management.
• Support new-site launches and ramp-ups from initial setup through stabilization.
• Provide leadership during operational disruptions and changing business conditions.

What We're Looking For

• 5+ years of experience in last-mile delivery, parcel logistics, express delivery, transportation, or related logistics operations.
• Strong experience in U.S. last-mile or parcel delivery operations.
• Hands-on experience independently managing a delivery station, hub, multiple operational sites, or regional operations.
• Experience working with DSPs, delivery contractors, transportation providers, or other delivery partners.
• Proven experience leading operational teams and developing frontline managers or site leaders.
• Experience with new-site launches, network expansion, rapid volume growth, or peak-season operations is strongly preferred.
• Strong understanding of operational KPIs, including service performance, productivity, utilization, cost, and delivery quality.
• Strong leadership, communication, analytical, and cross-functional collaboration skills.
• Ability to work on-site in the Chicago area and support regional operational needs.