Street Supervisor

Agupdate; Chestertown, Northern (MD, KY); Hybrid; USD 70,000 - 85,000; Full time

Benefits offered by this job

Health, dental, and vision insurance

Life insurance

Maryland State Retirement and Pension

Paid vacation and sick leave

Fourteen paid holidays

Professional development and training

Job summary

Town of Chestertown is seeking an experienced Street Supervisor to lead the daily operations of the Street Department, directing maintenance of streets, sidewalks, and public infrastructure and supervising a dedicated team.

The successful candidate will plan projects, ensure safety compliance, manage the budget, and coordinate staffing and equipment, with a focus on community service and high-quality Town services.

Qualifications

• High school diploma or equivalent required.
• Minimum of five years in public works or street maintenance with supervisory experience.
• CDL preferred.

Responsibilities

• Supervise street maintenance, repair, and construction activities.
• Plan and oversee snow removal operations for streets, parks, and walkways.
• Coordinate staffing, equipment, and supplies for department operations.
• Monitor projects with field inspections to ensure safety and quality standards.
• Assist with budget preparation and monitoring for the department.
• Ensure compliance with federal, state, and local safety regulations.

Skills

Leadership

Communication

Safety

Public works

Budgeting

Education

High school diploma

CDL preferred

Job description

Town of Chestertown - Street Supervisor

Job Summary

The Town of Chestertown is seeking an experienced, motivated, and hands-on Street Supervisor to lead the daily operations of the Street Department. This position is responsible for planning, directing, and supervising the maintenance and repair of Town streets, sidewalks, right-of-way, parks, and other public infrastructure. The Street Supervisor leads a dedicated team, manages projects and resources, ensures compliance with safety standards, and helps maintain the high quality of public services that residents rely on.

Essential Responsibilities

Supervise street maintenance, repair, and construction activities to ensure work is completed safely, efficiently, and in accordance with established quality standards. Conduct field inspections of projects to monitor progress, identify issues, and ensure compliance with safety regulations and Town policies. Plan, organize, and oversee snow removal operations for Town streets, parks, and public walkways. Supervise yard waste and bulk trash collection services. Coordinate staffing and logistics for Town events, including stage setup, barricades, and road closures. Assist with the preparation, administration, and monitoring of the departmental budget. Determine staffing requirements and coordinate the procurement and maintenance of equipment, materials, and supplies. Train, supervise, evaluate, and mentor assigned employees to promote a safe, productive, and collaborative work environment. Respond to inquiries and concerns from residents, contractors, and other departments, investigating complaints and implementing appropriate corrective actions. Ensure compliance with all applicable federal, state, and local safety regulations and Town policies.

Qualifications

Demonstrated leadership and supervisory experience. Ability to communicate effectively with employees, management, elected officials, and the public. Knowledge of street maintenance, construction practices, traffic control procedures, and workplace safety standards. Ability to interpret and apply applicable laws, regulations, policies, and procedures. Ability to conduct on-site inspections and evaluate work quality. Proficiency with modern office equipment and standard computer software.

Education & Experience

High school diploma or equivalent required. Minimum of five (5) years of progressively responsible experience in public works, street maintenance, construction, or a related field, including supervisory or management experience. Commercial Driver's License (CDL) preferred.

Salary Range

$70,000 to $85,000

Benefits include:

• Competitive health, dental, and vision insurance
• Life insurance
• Maryland State Retirement and Pension System
• Paid vacation and sick leave
• Fourteen (14) paid holidays
• Opportunities for professional development and training

The Town of Chestertown is an Equal Employment Opportunity Employer.

For more information about the Town of Chestertown, please visit our website.