Highway Maintenance Supervisor

Milwaukee-County; Milwaukee (WI); On-site; USD 42,000 - 62,000; Full time

Job summary

The Department of Transportation in Milwaukee County seeks a Highway Maintenance Supervisor to oversee crews performing maintenance, improvements, and snowplowing on Interstate, State, and County highways to keep the traveling public safe.

The role requires leadership, a Wisconsin CDL, and the ability to work irregular hours, overtime, and on-call shifts; travel may be needed. A minimum five years in highway maintenance and a valid CDL are essential.

Qualifications

• Minimum five years of Highway Maintenance experience.
• At least three years as Assistant Highway Maintenance Supervisor.
• High School Diploma or GED required.
• Valid Wisconsin Class B CDL with Airbrake Endorsement required.
• Willing to work irregular hours, including overtime, weekends or shift rotations.
• Willing and able to travel.
• Able to lift up to 60 lbs.
• Proficiency with Dayforce and CityWorks.
• Basic knowledge of word processing and spreadsheets.
• On-call availability.

Responsibilities

• Schedule, prioritize, assign, and direct the work of highway crews.
• Supervise the repair of roads, culverts, sewers, bridges, and curbs.
• Direct and train crews during snow removal and ice control operations.
• Direct and train crews on keeping grass and weeds under control.
• Investigate complaints from County Supervisors and citizens.
• Prioritize tasks according to their significance; address essential maintenance.
• Maintain records and reports including crew sheets and work orders.
• Enter employee times, equipment and work orders into Dayforce and CityWorks daily.
• Operate pickup trucks, power tools, and related equipment.
• Perform work on assigned shifts and respond to emergencies.
• Perform all other duties as assigned.

Skills

Leadership

Safety compliance

Equipment operation

Communication

Time management

Education

High School Diploma or GED

Tools

CDL Class B (Airbrake)

CDL Class A

Dayforce

CityWorks

Microsoft Word

Microsoft Excel

Job description

Highway Maintenance Supervisor

Department of Transportation

Hourly Pay Range:$30.19 - $45.29

Closing Date: September 16th, 2026, or upon receipt of the first 50 applications

Job Summary:

The Highway Maintenance Supervisor will assign, direct, and coordinate the work of highway crews in the maintenance, improvements, and snowplowing operations on the Interstate, State, and County trunk highways as directed by the State DOT and County officials. The major objective is to keep the motoring public, citizens, and employees of Milwaukee County safe. The Highway Maintenance Supervisor is also responsible for ensuring their staff is properly trained in all equipment as well as processes and are following safety standards required to complete maintenance projects.

Essential Responsibilities:

• Schedule, prioritize, assign, and direct the work of highway crews.
• Supervise the repair of roads, culverts, sewers, bridges, and curbs.
• Direct and train crews during snow removal and ice control operations.
• Direct and train crews on keeping grass and weeds under control.
• Investigate complaints from County Supervisors and citizens.
• Prioritize tasks according to their significance, ensuring that essential repairs such as asphalt, concrete, catch basin, curb and pan, guard-rail, barrel, fence, bridge rail, and additional necessary maintenance activities are appropriately addressed.
• Maintain records and reports in a timely manner, including crew sheets, work orders, reports to State DOT, tools, materials, and supplies.

• Enter employee times, equipment and work orders into Dayforce and CityWorks daily.
• Use of Equipment, Tools and Machinery – Operate pick-up trucks, single and tandem axle trucks, power tools, drills, torches, wrenches, paint sprayers, computers, copiers, and scanners.

• Perform work on any assigned shift, respond to emergencies when needed.

• Perform all other duties as assigned.

Minimum Requirements:

• Current resident of Wisconsin.
• Possession of a High School Diploma or GED equivalent.
• At least five (5) years of Highway Maintenance experience.
• At least three (3) years of experience as an Assistant Highway Maintenance Supervisor.
• Able to push, pull, lift, and carry up to 60 lbs.
• Possession of a valid Wisconsin Class B CDL with Airbrake Endorsement.
• Basic knowledge of all related computer and software applications, such as word processing and spreadsheets.
• Willing and able to work irregular hours including overtime, weekends, or shift rotations.
• Willing and able to have on-call availability, which includes unpredictable or long hours.
• Willing and able to travel in this role.

Preferred Qualifications:

• Possession of a valid Wisconsin Class A CDL.

NOTE:

This ORIGINAL APPLICATIONis open to qualified residents of the State of Wisconsin at the time of application.Candidates need to submit a full account of their training and experience (i.e., by submitting an up-to-date resume or by fully completing the application) during the application process and may also be asked to take additional written or performance tests as part of the selection process.

APPLICANTS MUST POSSESS MINIMUM QUALIFICATIONS AT TIME OF FILING APPLICATION