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Driver Supervisor Jobs in Boston, MA (NOW HIRING)

The Driver Supervisor is responsible for overseeing a specific group of drivers and monitoring performance and dispatch. This role involves managing the day-to-day functions of the Driver workforce ...

Driver Supervisor

Boston, MA · On-site

$48K - $68K/yr

The Driver Supervisor is responsible for overseeing a specific group of drivers and monitoring performance and dispatch. This role involves managing the day-to-day functions of the Driver workforce ...

Driver Supervisor

Boston, MA · On-site

$48K - $68K/yr

Overview The Driver Supervisor is responsible for overseeing a specific group of drivers and monitoring performance and dispatch. This role involves managing the day-to-day functions of the Driver ...

Driver Supervisor

Boston, MA · On-site

$48K - $68K/yr

Overview The Driver Supervisor is responsible for overseeing a specific group of drivers and monitoring performance and dispatch. This role involves managing the day-to-day functions of the Driver ...

Communicate frequently with peers, supervisors, and others. JOB DUTIES AND RESPONSIBILITIES ... Attend all driver workshops and training sessions * Use company supported applications or systems ...

Communicate frequently with peers, supervisors, and others. JOB DUTIES AND RESPONSIBILITIES ... Attend all driver workshops and training sessions * Use company supported applications or systems ...

Communicate frequently with peers, supervisors, and others. JOB DUTIES AND RESPONSIBILITIES ... Attend all driver workshops and training sessions * Use company supported applications or systems ...

Communicate frequently with peers, supervisors, and others. JOB DUTIES AND RESPONSIBILITIES ... Attend all driver workshops and training sessions * Use company supported applications or systems ...

Communicate frequently with peers, supervisors, and others. JOB DUTIES AND RESPONSIBILITIES ... Attend all driver workshops and training sessions * Use company supported applications or systems ...

Communicate frequently with peers, supervisors, and others. JOB DUTIES AND RESPONSIBILITIES ... Attend all driver workshops and training sessions * Use company supported applications or systems ...

Communicate frequently with peers, supervisors, and others. JOB DUTIES AND RESPONSIBILITIES ... Attend all driver workshops and training sessions * Use company supported applications or systems ...

Communicate frequently with peers, supervisors, and others. JOB DUTIES AND RESPONSIBILITIES ... Attend all driver workshops and training sessions * Use company supported applications or systems ...

Communicate frequently with peers, supervisors, and others. JOB DUTIES AND RESPONSIBILITIES ... Attend all driver workshops and training sessions * Use company supported applications or systems ...

Communicate frequently with peers, supervisors, and others. JOB DUTIES AND RESPONSIBILITIES ... Attend all driver workshops and training sessions * Use company supported applications or systems ...

This role oversees daily transportation operations, supervises drivers and helpers, ensures temperature-controlled and undamaged deliveries, maintains FIFO inventory practices at customer locations ...

This role oversees daily transportation operations, supervises drivers and helpers, ensures temperature-controlled and undamaged deliveries, maintains FIFO inventory practices at customer locations ...

This role oversees daily transportation operations, supervises drivers and helpers, ensures temperature-controlled and undamaged deliveries, maintains FIFO inventory practices at customer locations ...

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Driver Supervisor information

See Boston, MA salary details

$31K

$60.5K

$81.5K

How much do driver supervisor jobs pay per year?

As of Aug 29, 2026, the average yearly pay for driver supervisor in Boston, MA is $60,451.00, according to ZipRecruiter salary data. Most workers in this role earn between $52,200.00 and $62,500.00 per year, depending on experience, location, and employer.

What is a driver supervisor?

Driver Supervisors are professionals responsible for overseeing and managing a team of drivers within a company or organization. Their duties typically include scheduling routes, ensuring compliance with safety regulations, training drivers, monitoring performance, and handling any issues that arise during transport operations. They play a key role in ensuring that deliveries or transportation services run efficiently and safely. Driver Supervisors also act as a point of contact between drivers and management, helping to facilitate communication and resolve concerns.

What are the key skills and qualifications needed to thrive as a driver supervisor, and why are they important?

To thrive as a Driver Supervisor, you need strong leadership abilities, knowledge of transportation regulations, and experience in logistics or fleet management, often supported by a relevant diploma or certification. Familiarity with route planning software, GPS tracking systems, and safety compliance tools is typically required. Excellent communication, problem-solving, and organizational skills help in managing drivers and resolving operational challenges. These skills are crucial for ensuring efficient fleet operations, regulatory compliance, and high service standards.

What are some common challenges driver supervisors face in managing their teams, and how can they overcome them?

Driver Supervisors often encounter challenges such as coordinating schedules to ensure adequate coverage, addressing performance issues, and maintaining clear communication across a diverse team. Balancing compliance with safety regulations while meeting delivery deadlines can also be demanding. Successful supervisors overcome these hurdles by fostering open communication, providing regular training, and using route planning software to optimize efficiency. Building strong relationships with drivers and offering constructive feedback helps in promoting a positive work environment and reducing turnover.

What is the difference between Driver Supervisor vs Driver Manager?

AspectDriver SupervisorDriver Manager
CredentialsDriver's license, relevant certificationsDriver's license, management certifications (optional)
Work EnvironmentOversees daily driver operations, on-site supervisionManages multiple teams, strategic planning
Employer & Industry UsageLogistics, transportation companiesLarge fleet operations, transportation firms
Search & Comparison IntentOperational oversight, driver supervisionTeam management, operational strategy

The main difference is that a Driver Supervisor focuses on daily driver oversight and operational tasks, while a Driver Manager handles broader team management and strategic planning within transportation companies.

How much do driver supervisors make?

Driver supervisors typically earn a median annual salary of around $50,000 to $70,000, depending on experience, location, and the size of the company. They often oversee driver operations, ensure safety compliance, and may require certifications or relevant driving experience.

What are popular job titles related to Driver Supervisor jobs in Boston, MA?

For Driver Supervisor jobs in Boston, MA, the most frequently searched job titles are:

What job categories do people searching Driver Supervisor jobs in Boston, MA look for?

The top searched job categories for Driver Supervisor jobs in Boston, MA are:

Infographic showing various Driver Supervisor job openings in Boston, MA as of August 2026, with employment types broken down into 1% As Needed, 66% Full Time, 31% Part Time, and 2% Contract. Highlights an 99% Physical, and 1% Remote job distribution, with an average salary of $60,451 per year, or $29.1 per hour.

Greyhound Lines, Inc.
Ground Public Transportation • 5 - 10K employees

6.8

Company rating: 6.8 out of 10

Based on 21 frontline employees who took The Breakroom Quiz

72nd of 99 rated public transport

People enjoy working here

Paid breaks


$48K - $68K/yr

Full-time

Medical, Dental, Vision, Life, Retirement, PTO

Re-posted 6 days ago


Job description

The Driver Supervisor is responsible for overseeing a specific group of drivers and monitoring performance and dispatch. This role involves managing the day-to-day functions of the Driver workforce and ensuring pool compliance, effective employee/labor relations, driver retention, and safety performance.
Additionally, we are looking for a candidate with full availability who is willing to work weekends, holidays, and be on call.  
*Leadership role eligible for annual 10% bonus.*


  • Daily interaction with the driver workforce. Interviews, selects, trains, and manages the driver workforce.
  • Ensures all personnel have been trained and/or retrained according to operational procedures.
  • Follows up with new drivers at regular scheduled intervals on their performance.
  • Reviews manpower needs and ensures proper coverage, including managing driver dispatch for route personnel.
  • Ensures drivers are reporting to work on time and in complete uniform ready to work.
  • Ensures employee development by providing ongoing feedback to drivers concerning strengths and areas of needed improvement using DriveCam reporting and customer feedback.
  • Investigates and acts on feedback regarding drivers and safe operational practices.
  • Responsible for planning of future books offs and run change assignment.
  • Ensures compliance with safety standards, adherence to all DOT and FMCSA regulations.
  • Ensures that all company standards are met for all drivers in the areas of appearance, training, education, safety, and regulatory compliance.
  • Make sure drivers are properly credentialed to operate a commercial motor vehicle.
  • Work closely with HR to address all levels personnel matters.
  • Work with drivers to ensure good labor relations are maintained.
  • Ensure the following of the CBA to ensure proper handling of grievance process.
  • Review electronic DOT logs and/or paper DOT logs.
  • Monitors on-time performance on a real-time basis.
  • Manages employee performance, determining appropriate levels of discipline based on company policy, including executing termination if disciplinary action fails
  • Travel between locations may be required

  • Bachelor's degree preferred
  • 1+ year in operations experience
  • Excellent leadership, communication, and interpersonal skills
  • Ability to analyze data, generate reports, and make data-driven decisions
  • Ability to exercise considerable diplomacy, judgment, and discretion in establishing and maintaining good working relationships and discretion with the company and union officials
  • Safety and Workers Compensation, Labor relations, and CBA experience preferred
  • Proficient in Microsoft Office with emphasis on Excel, Windows applications, e-mail etc.

  • Comprehensive Wellness Coverage - Competitive Medical, Vision, and Dental plans, including multiple FSAs (Health and Dependent Care).
  • 401(k) Matching – 401(k) plan with up to 4% company matching contributions.
  • Flexible Time Off - Take time off when you need it, as you need it, subject to business needs and manager approval.
  • Paid Parental Leave - 8 weeks of fully paid leave to support new parents and growing families.
  • Company Paid Life Insurance – Basic company-paid life insurance equal to your annual salary.
  • Lifestyle Spending Account – Receive up to $600 per year for eligible lifestyle-related services.
  • Tuition Support - Up to $5,250 per year reimbursed for your continued education and development after 12 months of continuous service.
  • 24/7 Employee Assistance Program - Free, confidential support for mental health, legal, financial, and family issues, including up to 5 free counseling sessions per year.
  • Free Travel Perks – Complimentary travel on FlixBus and Greyhound for you and eligible dependents. 

USD $48,200.00 - USD $68,700.00 /Yr.

Greyhound is an Equal Opportunity Employer. We do not discriminate on the basis of race, color, religion, sex, sexual orientation, gender identity, national origin, disability, protected veteran status, age, genetic information, or pregnancy, or any other characteristic protected by law. Our policy of equal employment opportunity applies to all aspects of employment. We are committed to fostering a fair and merit-based workplace where every employee feels valued and respected. 



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