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City Manager - Chicago


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Company Overview

Dropoff provides reliable same-day delivery to enable businesses to meet rising customer expectations. National leaders in healthcare, retail and industrial partner with us to fulfill customer needs using our technology platform, professional drivers and proactive customer service. We are transforming the same-day delivery experience which is expected to be a $30 billion dollar business by 2025 in the United States. Rated as one of the best places to work in Austin, TX by the Austin American-Statesman and a proud recipient of Inc 5000’s Fastest Growing Private Companies in America, our sophisticated logistics platform allows enterprise businesses to gain visibility into their deliveries, improving customer experience and streamlining operations. 

For more information about how Dropoff is shaping the future of same-day delivery, visit

About the Opportunity

Searching for your next challenge? We are looking for a City Manager (based out of Chicago, IL).

The City Manager’s primary focus is to ensure excellence and consistency in local market

operations. This includes continuous recruitment for both employee and independent

contractor drivers in assigned markets. City Managers assume responsibility for all local market KPIs, including on-time delivery, local market expenses as a percentage of revenue, and customer satisfaction. City Managers are the subject matter experts for all local market

operational activities, with a deep understanding of local market geographies. The ideal

candidate will have a minimum of 5 years of experience in managing local or regional operations teams. Experience with last-mile logistics and medical services is a plus.

This position reports to the General Manager.


● Ensure the proper supply of driver capacity to successfully manage customer delivery

demand for assigned markets.

● Recruit, train and provide ongoing supervision of the local market driver fleet.

● Provide ongoing development programs for drivers to ensure consistent success in

meeting delivery KPIs.

● Monitor daily order flow and driver performance to improve market performance.

● Make proactive recommendations to senior leadership to improve overall market


● Determine market needs for delivery vans and other equipment. Prepare business case

and/or provide the necessary documentation to request approval for expenses.

● Manage the cost of service (driver and equipment fees) to strike an optimal balance between service performance and operating margins.

● Work in partnership with Client Success, Account Management, and Dispatch leadership

regarding market operational performance.

● Partner with sales team members to assist with new client acquisition, including

in-person meetings with key decision-makers on an as-needed basis.

● Partner with client success management to optimize the performance of existing accounts.

Identify and address key improvement areas to assure ongoing client satisfaction.

● Assume responsibility with client success for customer ratings and net promoter scores.

Skills & Experience

● Proven ability to work independently and make good decisions with minimal direction

● Clear and precise communication skills - both written and verbal

● Strong leadership skills, with an ability to both serve and direct team activities

● Positive interpersonal skills, maintaining a positive attitude while working with

individuals in different departments and in pressured situations

● Analytical skills – analyze complex data, draw accurate conclusions, make business


● Strong problem-solving skills, with an ability to react quickly and works well in a dynamic


*Note - some travel is required*

Dropoff Benefits

  • Stock options (every employee  is an owner in the company)

  • Great Healthcare Plan for you and your dependents (we help you out with the cost!)

  • Flexible vacation policy (work/life balance is important to us!)

  • Culture (We are an inclusive team who celebrates our unique talents) 

  • Room to grow your career (we encourage internal career progression and are proud to see our team members take on new roles!) 

Dropoff is proud to be an equal opportunity employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, gender, gender identity or expression, sexual orientation, national origin, genetics, disability, age, or veteran status

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