Street Supervisor

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

Interested candidates should submit a cover letter and resume to Town of Chestertown, Attention: Human Resources, 118 N Cross Street, Chestertown, MD 21620 by August 21, 2026.

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

The Town of Chestertown is an Equal Employment Opportunity Employer.