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Crew Leader-Trail Maintenance

Chesapeake, VA

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.PDN-a240e734-92d8-4405-b6e2-f9d80170e697
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.PDN-a240e734-92d8-4405-b6e2-f9d80170e697

About City of Chesapeake

Chesapeake, Virginia is a vibrant community that enjoys the best of two worlds, one of urban variety, culture, and excitement, and another of rural landscapes and relaxed living. 

Located 20 minutes from the oceanfront, 15 minutes from downtown Norfolk, and 45 minutes from Colonial Williamsburg and the Outer Banks of North Carolina, Chesapeake is the perfect place in which to live, work, and raise a family. 

Home to beautiful parks, lakes, and rivers, Chesapeake has more miles of deepwater canals (part of the Intracoastal Waterway) than any other city in the country! 

The City of Chesapeake was formed through the merger of the City of South Norfolk and Norfolk County in 1963. It’s a community of communities, with each having its own distinctive history. 

Over the last decade, many national and international companies have taken advantage of the City’s ports, atmosphere, and highly qualified labor market by relocating to Chesapeake. 

Chesapeake’s neighborhoods offer a variety of comfortable housing alternatives, from apartments and town homes, to single-family residences and executive homes. The City is consistently ranked by the FBI as one of the safest U.S. cities (with populations over 150,000), which lends to the safe, community atmosphere that residents enjoy.

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City of Chesapeake
Crew Leader-Trail Maintenance
City of Chesapeake
Chesapeake, VA
Jul 14, 2026
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