City Manager, Boston

Dropoff, Inc.

Boston, MA, USA

Posted on Jun 13, 2026

Apply now

Company Overview

Dropoff provides reliable same-day delivery, empowering businesses to meet and exceed rising customer expectations. Trusted by national leaders in healthcare, retail, and industrial sectors, we partner with enterprises to fulfill critical customer needs through professional drivers and proactive customer service.

We are transforming the same-day delivery experience in a rapidly growing U.S. market. Recognized 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, Dropoff’s sophisticated logistics platform gives enterprise businesses real-time visibility into their deliveries—improving customer experience while streamlining operations at scale.

For more information about how Dropoff is shaping the future of same-day delivery, visit https://www.dropoff.com.

The Opportunity

Searching for your next challenge? If so, we are looking for a City Manager, Boston, based in the Boston, Massachusetts area.

The primary focus of the City Manager, Boston, is to ensure excellence and consistency in local market operations across a number of metropolitan areas within a defined region. This includes continuous recruitment for independent contractor drivers in assigned markets. City Managers assume responsibility for on-time delivery, local market operational expenses, and customer satisfaction. The ideal candidate will have operational management and/or customer service experience. Experience with last-mile logistics and medical services is a plus. This is an entry-level management position.

This position reports to the General Manager.

Responsibilities

• Ensure proper supply of driver capacity to manage customer delivery demand for assigned markets successfully.
• Recruit, train and provide ongoing supervision of the local market driver fleet.
• Assist with weekly driver payroll to ensure accuracy each week.
• Monitor daily order flow and driver performance to improve market performance.
• Make proactive recommendations to senior leadership to improve the overall market performance.
• Work in partnership with Customer Service and Account Management staff to provide consistent service and react/respond to service escalations on a timely basis.
• Actively work in partnership with Dispatch staff to monitor order flow, delivery assignment, and timely delivery completion by drivers.
• Partner with client success management to optimize the performance of existing accounts.
• Identify and address key improvement areas to assure ongoing client satisfaction.
  
  

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
• Strong Analytical skills (you will need to review complex data, draw accurate conclusions, and make business recommendations)
• Strong problem-solving skills, with an ability to react quickly and work well in a dynamic environment
• Experience in same-day delivery or healthcare logistics is a plus
• Note: This is a hybrid role. Candidates must have access to reliable transportation, as periodic travel to client sites or meetings is required.
  
  

Dropoff Benefits

• Stock options (every employee is an owner in the company)
• Competitive Healthcare Plan for you and your dependents
• 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

Apply now

See more open positions at Dropoff, Inc.

Responsibilities

• Ensure proper supply of driver capacity to manage customer delivery demand for assigned markets successfully.
• Recruit, train and provide ongoing supervision of the local market driver fleet.
• Assist with weekly driver payroll to ensure accuracy each week.
• Monitor daily order flow and driver performance to improve market performance.
• Make proactive recommendations to senior leadership to improve the overall market performance.
• Work in partnership with Customer Service and Account Management staff to provide consistent service and react/respond to service escalations on a timely basis.
• Actively work in partnership with Dispatch staff to monitor order flow, delivery assignment, and timely delivery completion by drivers.
• Partner with client success management to optimize the performance of existing accounts.
• Identify and address key improvement areas to assure ongoing client satisfaction.
  
  

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
• Strong Analytical skills (you will need to review complex data, draw accurate conclusions, and make business recommendations)
• Strong problem-solving skills, with an ability to react quickly and work well in a dynamic environment
• Experience in same-day delivery or healthcare logistics is a plus
• Note: This is a hybrid role. Candidates must have access to reliable transportation, as periodic travel to client sites or meetings is required.
  
  

Dropoff Benefits

• Stock options (every employee is an owner in the company)
• Competitive Healthcare Plan for you and your dependents
• 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