Crew Leader-Trail Maintenance

City of Chesapeake Virginia; Chesapeake (VA); On-site; USD 50,000 - 67,000; Full time

Job summary

The City of Chesapeake is seeking a Crew Leader in the Planning/Urban Forestry Division of Parks, Recreation and Tourism. You will supervise groundskeeper and motor equipment operator crews, lead daily assignments and ensure safe, efficient performance across trails, landscapes and city facilities.

Responsibilities include operating equipment, mentoring staff, coordinating with contractors, and maintaining records.

Qualifications

• Requires high school diploma, GED / HSE or any equivalent combination of education and experience.
• Minimum of one year of related, full-time equivalent experience.
• A Class A Commercial Driver’s License (CDL) is required at the time of hire.
• Special skills or equipment certification may also be required.
• Pesticide application certification within 6 months of hire preferred.

Responsibilities

• Oversees, participates and reviews work assignments, ensures staff have the proper tools, equipment and supplies.
• Oversees and participates in skilled and semi-skilled work with various equipment.
• May supervise inmate crews from Sheriff’s Department workforce program.
• Provides logistical support for City-sponsored functions and events.
• Performs safety inspections and ensures repairs for safety.

Skills

Leadership

Reading plans

Basic computer skills

Communication skills

Education

High school diploma or GED

Tools

CDL Class A

Pesticide application certification

Job description

Please see Special Instructions for more details.

Drug Screening: MARIJUANA

In accordance with City policy, this position is deemed safety-sensitive. As such, applicants for this position are subject to pre-employment drug/alcohol testing after receiving a conditional offer of employment and may also be subject to random testing. This drug test includes testing for marijuana. Possession of a medical marijuana card will not excuse an applicant from the testing process; however, a test will not be considered positive for marijuana if a valid medical marijuana certification is presented unless the position requires a commercial driver’s license (CDL) or is a sworn law-enforcement officer/deputy.

Employees may be expected to work hours in excess of and/or outside of their normally scheduled hours in response to short-term department needs and/or City wide emergencies. Emergency operations support work and work locations may be outside of normal job duties.

Position Information

Working Title of Vacant Position

Job Type

Job Type Full Time

Posting Type

Posting Type Public

Number of Vacancies

Number of Vacancies 1

Department

Department PARKS, REC, & TOURISM

Division

Division PR&T MUNI GROUNDS MAINT

Requisition Number

Requisition Number 2026337

Number of hours worked per week

Number of hours worked per week 40 +

Work Schedule

Includes Mon.- Fri. routine hours are 7 am – 3:30 pm, will be based on operational requirements. Days, evenings, weekends, occasional holidays, and overtime may be included.

Work Site Location

Work Site Location Chesapeake, VA

Position Driving Requirement

Position Driving Requirement R - Routine

Pay Grade

Pay Grade GE11

Pay Basis

Pay Basis Semi-Monthly

Advertised Salary

Starting Salary: $55,854 Annually
Starting salary based on qualifications and experience.

Job Description

Do you have knowledge of grounds and trail maintenance? Are you great at leading and inspiring employees? If you answered yes to these questions, apply NOW ! The Planning/Urban Forestry Division of Chesapeake Parks, Recreation and Tourism has an opening for a Crew Leader.
This position is primarily responsible for overseeing, leading and participating in the daily scheduled work assignments of groundskeeper and/or motor equipment operator crews. Leads crews to include tree removal and installation, trail maintenance, invasive plant removals, landscaping, special projects, routine maintenance, and logistical support for city sponsored functions and special events in parks and open spaces located throughout the city. Supports the maintenance of city facilities and outdoor spaces such as multipurpose trails, park grounds, municipal facilities, right of way areas, recreational and historical facilities, park amenities and fields. Crew work activities will involve operating heavy specialized motor equipment, power tools and hand tools, perform routine and skilled tasks such as tree work, grading, mowing and trimming of turf, landscaping, planting, mulching, weeding, fertilizing, spraying, pruning trees and shrubs, painting, material applications, edging, paving, drainage, removing dead vegetation and wood debris, and perform repairs and construction. Cleans and stocks restrooms, concessions, campsites and storage facilities. Crew Leader tasks will include but are not limited to:

• Oversees, participates and reviews work assignments, ensures staff have the proper tools, equipment and supplies to complete assignments and work is perform efficiently and safely.
• Oversees and participates in skilled and semi-skilled work, mowing, trimming, edging, cutting, fertilizing, mulching, chemical application, surface repairs, construction, installations, custodial, trash removal and other general maintenance assignments. Working with various type of general and specialized equipment from hand tools such as chain and pole saws up to heavy equipment such as a backhoes, tractors, graders or dump trucks.
• May supervise work inmate crews from the Sheriff’s Department workforce program.
• May participate in providing logistical support for City sponsored functions and special events; set-up and breakdown tents, fencing, barricades, and other various recreational and sound equipment, preform post event activities such as clean-up and trash removal.
• Preforms safety inspections of trees, trails, turf area, parking lots, parks, fields, restrooms, recreational facilities, park amenities, and sidewalks, and ensures that the required repairs are completed, to ensure the safety of citizens, participants, employees, and visitors.
• Secures and prepares resources to complete work requirements, assigns duties, tasks and routes, trains subordinate staff as necessary, recommends effective work methods, assists with problem solving and ensures compliance with all safety requirements, laws and policies.
• Ensures all equipment in use is in proper working order and is in compliance with all safety standards, requirements, laws and policies; promptly reports any deficiencies to supervisor. Performs routine and general maintenance of equipment used.
• Assists with staff organization and development, work schedules, hiring and interviewing, performance evaluations, employee relations, prioritizing work-related activities.
• Interacts with the public, contractors, citizens and other agencies in person, by email, fax and telephone to resolve concerns and inquiries, problem solves and conveys information as assigned.
• Provides customer service relations to a diverse population that meets the expectations of the City’s Customer Care standards.
• Completes and maintains various logs, forms, work orders, material expenditures and other related records for assigned areas. Gathers and maintains information to support periodic and special reports documenting activities and events for area of responsibility.
• Operates various lawn and garden equipment, saws, commercial tractor and mowers, backhoe, graders, snowplows, City vehicles, trailers, dump truck, utility vehicles, common hand and power tools associated with groundskeeping, custodial, landscaping and building maintenance.
• Assists with contract specifications, monitors and inspects contractor performed work to ensure compliance.
• Assists with inventory, contract specifications, budgets, purchasing, compiling data, and reporting.
• Maintains assigned inventory, parts, materials and equipment.
• Performs various clerical tasks such as timekeeping, data entry, phoning, emailing, faxing and copying.
• Attends staff meetings, training sessions, seminars, conferences, and classes to exchange information and improve skills.
• Performs other duties as assigned.

The City of Chesapeake offers an exceptional range of benefits. Please browse our Benefits Brochure, for a full list of benefits and employee perks.

Required Qualifications

VOCATIONAL / EDUCATIONAL REQUIREMENT :
Requires high school diploma, GED / HSE or any equivalent combination of education and experience.
EXPERIENCE REQUIREMENT :
In addition to satisfying the vocational/education standards, this class requires a minimum of one year of related, full-time equivalent experience.
SPECIAL CERTIFICATIONS AND LICENSES :

• A Class A Commercial Driver’s License ( CDL ) is required at the time of hire.
• Special skills or equipment certification may also be required.

SPECIAL REQUIREMENTS :

Employees may be expected to work hours in excess of their normally scheduled hours in response to short-term department needs and/or City-wide emergencies.

Preferred Qualifications

• Ability to read and understand drawings and simple to complicated plans in the maintenance of trails, landscapes, and facilities.
• Basic computer skills and ability to write, read and use a calculator.
• Have at least two years of supervisor experience in grounds keeping, landscaping, horticulture, facilities maintenance or other related field.
• Secure pesticide application certification within 6 months of hire.
• Knowledge of standard operations and best practices for general grounds keeping, landscaping, repair work and maintenance.

Job Open Date

Job Open Date 08/21/2026

Job Close Date

Job Close Date 09/08/2026

Open Continuous No

Special Instructions to Applicants

Drug Screening: MARIJUANA

In accordance with City policy, this position is deemed safety-sensitive. As such, applicants for this position are subject to pre-employment drug/alcohol testing after receiving a conditional offer of employment and may also be subject to random testing. This drug test includes testing for marijuana. Possession of a medical marijuana card will not excuse an applicant from the testing process; however, a test will not be considered positive for marijuana if a valid medical marijuana certification is presented unless the position requires a commercial driver’s license ( CDL ) or is a sworn law-enforcement officer/deputy.

Employees may be expected to work hours in excess of and/or outside of their normally scheduled hours in response to short-term department needs and/or City wide emergencies. Emergency operations support work and work locations may be outside of normal job duties.