City Manager, Boston

Dropoff
Boston, MA

Job Description

Job Description

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, 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

The Opportunity

Searching for your next challenge? We are looking for a City Manager based out of Boston, Massachusetts.

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. This is an entry level management position.

This position reports to the General Manager.

Responsibilities

● Ensure a 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 KPI's

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

● Make proactive recommendations to senior leadership to improve overall market performance.

● Determine market needs for delivery vans and other equipment. Prepare a business case and/or provide the necessary documentation to request approval for expenses.

● 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 and advocacy.

● Assume responsibility for 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 recommendations

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

This is a consultant-to-hire position. Benefits are eligible following consultant period

Dropoff Benefits

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

● Competitive Healthcare Plan for you and your dependents

● Flexible vacation policy

● Culture (We are an inclusive team that 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.

Posted 2025-07-29

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