Regional Last Mile & Delivery Operations Manager (Chicago)

Location: Chicago

Employment Type: Full-time

Build, Scale and Lead Last-Mile Operations

We are looking for an experienced Regional Last Mile & Delivery Operations Manager to lead and scale our last-mile delivery operations across the region.

This is a highly visible leadership role for someone who understands what it takes to run a fast-moving delivery network — from delivery stations and transportation capacity to DSP performance, service quality, cost efficiency, and peak-season execution.

You will take ownership of regional operational performance and work closely with site leaders, DSP partners, transportation teams, and cross-functional stakeholders to build a reliable, scalable, and efficient last-mile network.

If you have experience running delivery stations, hubs, multi-site operations, or regional last-mile networks — and enjoy building operations that can scale — this could be an exciting opportunity to make a significant impact.

What You'll Do

• Lead end-to-end last-mile and delivery operations across an assigned region, with responsibility for service performance, delivery quality, cost efficiency, productivity, and operational execution.
• Oversee multiple delivery stations, warehouses, hubs, or operational sites and ensure consistent day-to-day performance across the network.
• Manage relationships and operational performance with Delivery Service Partners (DSPs) and other transportation partners, including capacity planning, onboarding, performance improvement, and service quality.
• Partner with site leaders and operations teams to identify operational gaps, improve execution, and build scalable processes.
• Lead regional planning for peak periods and changing business volumes, ensuring the network is prepared to support growth.
• Manage regional operating budgets and identify opportunities to improve productivity, capacity utilization, and cost per package.
• Use operational data and performance metrics to identify trends, uncover improvement opportunities, and drive measurable results.
• Build, develop, and lead regional operations teams, including frontline leaders and site management.
• Support the launch and ramp-up of new delivery stations or operational sites, from initial setup through stabilization and growth.
• Improve operational processes and SOPs across sorting, transportation, delivery, and last-mile execution.
• Partner closely with headquarters, internal functions, and external partners to align resources and support regional business goals.
• Provide leadership during operational disruptions and changing business conditions, helping teams prioritize, make decisions, and restore stable operations.

What We're Looking For

• 5+ years of experience in last-mile delivery, parcel logistics, express delivery, transportation, warehouse operations, or related logistics environments .
• Experience in U.S. last-mile, parcel delivery, delivery station, or logistics operations is strongly preferred.
• Experience independently managing a delivery station, hub, multiple sites, or regional operations .
• Experience working with DSPs, delivery contractors, transportation providers, or other delivery partners .
• Demonstrated experience leading sizable operational teams and developing frontline managers or site leaders.
• Experience supporting new-site launches, network expansion, rapid volume growth, or peak-season operations.
• Strong understanding of operational KPIs, including service performance, productivity, utilization, cost, and delivery quality.
• Strong business judgment, ownership, and ability to balance customer experience, operational efficiency, and cost.
• Comfortable using operational data to make decisions and drive continuous improvement.
• Strong leadership, communication, and cross-functional collaboration skills.
• Fluent English communication skills; Mandarin or Chinese language skills are a plus.

Why This Role

This is an opportunity to play a key role in building and scaling a growing last-mile delivery network.

You will have the opportunity to work across operations, delivery partners, transportation capacity, site expansion, and regional performance — with the ability to directly influence how the network grows and operates.

If you enjoy solving complex operational challenges, building strong teams, and creating scalable delivery operations, we would love to hear from you.