Highway Maintenance Assistant Supervisor

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Milwaukee County offers a wide variety of interesting jobs for people who want to make a difference in our community. Milwaukee County provides a competitive benefit package and is an Equal Opportunity Employer. If disability related accommodations are needed, please email View email address on aiapply.co. For submitted application inquiries please contact View email address on aiapply.co. Please note: an online application must be submitted for consideration.

We are searching for Changemakers to come and join our team and discover our diverse and versatile community of independent spirits and unique talents, we are redefining the way you think about Milwaukee County!

Closing Date: October 1st, 2026, or upon receipt of the first 50 applicant submissions

Highway Maintenance Assistant Supervisor

Department: Department of Transportation – Highway Maintenance

Full-time, Hourly

Hourly Range: $28.50 - $42.73/hr

Job Summary

This position is responsible for assigning, directing and coordinating 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 Department of Transportation and County officials. The major objective is to keep the motoring public and the citizens of Milwaukee County safe. This position is subject to constant traffic changes, weather conditions and is required to respond to emergencies on the roadways.

Work Schedule: Employee must have availability to workdays, evenings, nights and weekends as needed. Employee must also have regular and frequent on-call availability to work irregular, unpredictable, and particularly long hours due to frequent overtime, weekends and shift rotations as needed. Employee must also make adjustments to schedules within minutes if an emergency were to arise.

Job Responsibilities

• Schedule, prioritize, assign and direct the work of highway crews.
• Supervise the repair of roads, culverts, sewers, bridges and curbs.
• Direct crews during snow removal and ice control operations.
• Direct crews to see that grass and weeds are kept under control.
• Investigate complaints from County Supervisors and citizens.
• Maintain records and reports in a timely manner including crew sheets, work orders, reports to State Department of Transportation, tools, materials and supplies.
• Perform work on any assigned shift and respond to emergencies when needed.

• 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.
• Schedule mowing on approximately 3,300 acres of Interstate, state and county trunk roadway.

• Enter employee times, equipment and work orders into Dayforce and CityWorks daily.
• Other duties as assigned.
• 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.

Required Education, License/Certification and Experiences

• Current residency within the State of Wisconsin upon application required
• Valid Wisconsin Driver’s License required and must be maintained throughout incumbency
• High School diploma or GED required
• At least three (3) years or more work experience in Highway Maintenance required.
• Basic knowledge of all related computer and software applications, such as word processing and spreadsheets required.
• Valid Class B Commercial Driver’s License (CDL) with no airbrake restriction required at the time of application and maintained during employment
• Ability to lift, push, pull and carry up to 60lbs.

Preferred Qualifications:

• Valid Class A Commercial Driver’s License (CDL) with no airbrake restriction at the time of application and maintained during employment preferred.
• Previous supervisory or management experience or completion of Milwaukee County Department of Transportation Management Program preferred.

NOTE: This ORIGINAL APPLICATION is 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

Milwaukee County is committed to fostering an equitable working environment , free from discrimination and harassment , on the basis of any characteristic protected by law. We prohibit any form of discrimination , harassment based on race, color, religion, sex, gender, gender identity or expression, sexual orientation, pregnancy, pregnancy related condition, national origin, age, disability, FMLA status, sexual orientation, military status, marital status, or any other category or status that is now or in the future protected by federal, state, and local law. We maintain a drug-free workplace and perform pre-employment substance abuse testing, background checks and pre-employment physicals subject to job requirements. If special accommodations are needed, please contact View phone number on aiapply.co.