Maintenance Operator II (Roadways/Sidewalks/Trees)

Winter Haven; Winter Haven (FL); On-site; USD 36,000 - 60,000; Full time

Benefits offered by this job

Medical Insurance

Dental Insurance

Vision Insurance

Life Insurance

12 Paid Holidays

12 Vacation Days

12 Sick Days

401(a Retirement Plan

457 Deferred Plan Options

Education/Tuition Assistance

Training and Development

Employee Assistance Program

Job summary

Winter Haven City seeks a hands-on Maintenance Operator II to maintain roadways, sidewalks, and trees, ensuring safe, clean, and attractive public spaces. You will work outdoors as part of a compact, multi-talented team across city infrastructure projects.

Responsibilities include performing routine maintenance, coordinating with project plans, supporting utility locates, and assisting in emergency response.

Qualifications

• Graduation from high school or equivalent is required.
• Experience with roadway, sidewalk, and tree maintenance is preferred.
• Ability to operate related tools and heavy equipment safely.

Responsibilities

• Plan and perform routine roadway and sidewalk maintenance and repairs.
• Assist in tree care tasks and equipment maintenance.
• Support project planning, utility locates, and material ordering.

Skills

Equipment operation

Roadways/sidewalks maintenance

Tree maintenance knowledge

Safety awareness

Communication skills

Ability to learn new tools

Education

High school diploma or equivalent

APWA MOT training (Public Works Math 101 / Intermediate MOT)

Tools

Backhoe

Skid-steer

Mini-track hoe

Hydraulic lift

Stump grinder

Chain saws

Job description

Maintenance Operator II (Roadways/Sidewalks/Trees)

Are you someone who enjoys working outdoors, making a visible impact in your community, and taking pride in keeping public spaces safe, clean, and beautiful? We’re looking for a hands-on, dedicated Maintenance Operator to help maintain and enhance our sidewalks, roadways, and trees.

• Job Title: Maintenance Operator II (Roadways/Sidewalks/Trees)
• Category: Full-Time
• Application Closing Date: October 25, 2026, 5:00 p.m.
• Annual Step for Performance Pay Adjustments
• 12 Paid Holidays Per Year
• 12 Vacation Days Minimum, Earned Per Year
• 12 Sick Days Earned Per Year
• Medical, Dental, Vision, and Life Insurance Benefits
• 401(a) Retirement Plan and Social Security Coverage
• 457 Deferred Plan Options
• Education/Tuition Assistance Program; and Training and Development Opportunities
• Employee Assistance Program – to include Mental Health Assistance/Services

Works as part of a compact multi-talented team in a growing community maintaining, repairing, and improving roadways, pedestrian infrastructure, and providing sustainability for a healthier urban canopy throughout the City.

• Roadways: Duties include but are not limited to preforming maintenance and repairs on a revolving repair and improvement worklist, and performing scheduled routing maintenance of equipment used to perform job duties. Functions also include providing support on utility locates and ordering materials needed to complete a proper roadway repair or new installation, collaborating on and reviewing project plans, helping to track project progress from conceptualization through finalization, and ensuring a safe working environment. This position functions as part of a multi-disciplined team and will also be involved in other aspects of maintaining public infrastructure.
• Sidewalks: Supports the Division by working to construct, maintain, repair, and improve the City’s pedestrian infrastructure. Duties to include but are not limited to planning and constructing new pedestrian connections, performing maintenance and repairs on a revolving repair and improvement worklist, and performing scheduled routing maintenance of equipment used to perform job duties. Functions also include providing support on utility locates and ordering materials needed to complete a proper sidewalk repair or new installation, collaborating on and reviewing project plans, helping to track project progress from conceptualization through finalization, and ensuring a safe working environment. This position functions as part of a multi-disciplined team and will also be involved in other aspects of maintaining public infrastructure.
• Trees: Supports the Division and crew leader as a vital member of the tree maintenance team, contributing to the care, preservation, and enhancement of the City's urban tree canopy.

Responsibilities include but are not limited to planning and executing tree maintenance tasks, performing routine and corrective tree care, maintaining and servicing equipment essential to the job, and ensuring the safety of the crew and the public during tree-related activities.

In addition to tree-related duties, this role collaborates on project plans and contributes to the monitoring of project progression, from initial planning to completion. Procuring necessary materials for tree care operations and assisting in utility locates are also essential job functions.

Must be available to perform essential job function outside of regular work hours responding to emergency situations, mostly based on “subject to call” scheduling. This is not intended to be an all-inclusive listing of essential job functions; the performance of other essential functions may be required.

Knowledge, Skills & Abilities:

• Knowledge and experience with the operation of related tools (shovels, circular saws, demo saws, tampers, levels, tape-measures, etc.) and equipment (backhoe, skid-steer, mini-track hoe, etc.
• Knowledge of construction operations (quantity estimation, installing or repairing proper roadway infrastructure).
• Continuing education in constructing roadway improvements will be a requirement of this role.
• Knowledge and experience with the operation of masonry craftsmanship related tools (shovels, circular saws, demo saws, tampers, trowels, levels, tape-measures, etc.) and equipment (backhoe, skid-steer, mini-track hoe, etc.)
• Knowledge of construction operations (quantity estimation, installing or repairing proper ADA compliant sidewalk infrastructure, curb ramps), and the knowledge and understanding of the FDOT Design Standards and Specifications for proper sidewalk and ramp application.
• Continuing education in constructing pedestrian improvements will be a requirement of this role.
• Knowledge and experience with tree maintenance and preservation specialty.
• Must have experience with driving or operating specialized equipment (hydraulic lift and bucket, stump-grinder, verity of chain-saws, hand-pruners etc.)
• Management and supervision (safety awareness, assessing tree damaged condition along streets and park grounds, receives and reviews requests for tree services, etc.),
• Recommends the removal or pruning of existing trees;
• Reviews construction plans and makes recommendations to preserve existing trees within the city’s right-of-way.
• Must remove fallen and standing trees from city streets or park areas; trim branches from trees in order to preserve pedestrian and motorist visibility of street signs, stop signs and traffic lights; rigs, cuts, and removes dead or diseased tree members employing slings and ropes.
• Basic computer literacy (ability to compose an e-mail, provide updates in simple report form, interact with timekeeping and asset management software, etc.)
• Ability to communicate effectively with internal and external customers (written and oral).
• Must be prepared to learn and adapt as new tools, processes, and practices become available.
• Must be able to aid in the development of less experienced personnel through coaching and training (under the guidance of superintendent or designee).
• As part of an emergency response unit, must be able to handle a rapid change of direction associated with environmental conditions.

• Graduation from an accredited high school or possession of an acceptable equivalency diploma.
• Three years of experience in a field requiring similar knowledge, abilities, and skills.
• Roadways and Sidewalks: Preferred training and experience include American Public Works Association (APWA) Public Works Math 101 and Intermediate MOT.
• Trees: Preferred training and experience include; Intermediate MOT.

An equivalent combination of training, education, and experience that is determined to be directly related to the foregoing specific requirements may be substituted.

Special Requirements:

• Possession of or the ability to obtain within one (1) year of employment a valid Florida Class B driver’s license with air brake and endorsement.
• Must have a good driving record as determined by the City of Winter Haven.
• Absence of non‑prescribed controlled substances in the applicant’s system as verified by a laboratory approved by the City of Winter Haven.

Physical / Environmental Factors:

• Must have the physical ability, strength, and flexibility to perform the essential job functions in the work environment.
• Requires physical work that involves walking, standing, driving, climbing, and exerting up to 95 pounds of force on a routine basis.
• Considerable skill, adeptness, and speed in the use of the fingers, hands, or limbs in tasks involving close tolerances.
• Must be able to perform manual labor in adverse conditions including confined spaces.
• Reasonable accommodations will be made for otherwise qualified individuals with a disability.

AN EQUAL EMPLOYMENT OPPORTUNITY EMPLOYER AND A DRUG-FREE WORKPLACE

Our Mission: Enriching lifestyle through exceptional service.

Category Full Time Status Open Posted October 9, 2026 10:10 AM Closing October 25, 2026 5:00 PM

Physical Address

500 Third Street NW

Winter Haven , FL 33881