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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.
- Application: Click Here

Salary And Benefits

- $18.10 Per Hour Minimum
- 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

APPLY NOW Essential Job Functions 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

- Roadways Maintenance
- 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.
- Sidewalks
- 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.
- Trees
- 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 recent 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.

Minimum Education & Experience

- 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.

APPLY NOW AN EQUAL EMPLOYMENT OPPORTUNITY EMPLOYER AND A DRUG-FREE WORKPLACE Our Mission: Enriching lifestyle through exceptional service.

Job Details

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

📌 Maintenance Operator II (Roadways/Sidewalks/Trees) (Uluberia)
🏢 Winter Haven Regional Airport
📍 Uluberia