Field Operations Supervisor - Landscaping & Maintenance

Field Operations Supervisor - Landscaping & Maintenance

Base pay range

$22.00/hr - $26.00/hr

Milwaukee Community Service Corps (MCSC) is a nonprofit organization that empowers at-promise, unemployed and underemployed individuals through education, job training, and life skills. We provide real-world work experience that improves both lives and neighborhoods across Milwaukee. You’re not just maintaining landscapes, you are helping people grow. Many of our crew members are overcoming barriers to employment. Your leadership helps them build confidence, skills, and a path forward.

As a Field Operations Supervisor, you will be one of our boots-on-the-ground leaders for our landscaping and maintenance crews. You’ll guide teams of trainees as they complete essential projects that beautify and maintain public and private spaces throughout our community. This hands-on role combines leadership, technical skills, and mentorship. You’ll be outdoors most of the time, managing crews, operating equipment, and ensuring that every project is completed safely, efficiently, and to high standards.

• Lead and supervise crews on a variety of projects including:
• Turf maintenance
• Landscaping and planting
• Tree trimming and brush clearing
• Snow and ice removal
• General site cleanup, maintenance, portering services
• Train and mentor crew members—many of whom are gaining their first job experience or re-entering the workforce
• Ensure safety by enforcing OSHA and MCSC safety protocols and leading by example
• Operate and maintain landscaping tools and equipment (e.g., mowers, trimmers, snowplows, wood chippers)
• Track and report timecards, job progress, and crew performance
• Adapt to weather and seasonal demands—some evening or weekend work may be required

Required:

• High school diploma or equivalent
• Valid Wisconsin driver’s license and insurable driving record
• Reliable transportation to/from MCSC’s Milwaukee office
• Strong communication and leadership skills
• Experience with landscaping tools and outdoor maintenance
• Ability to lift 50 pounds and work in all weather conditions

Preferred:

• 1+ year of supervisory or crew leadership experience
• Experience mentoring or training others
• Familiarity with snowplows, stump grinders, chain saws, and wood chippers
• Background working with at-promise or underserved populations

• 13 Paid Holidays
• 2 Weeks Paid Time Off (Year
  1); increases with tenure
• 403B Retirement Plan (Up to 7% match + 1% employer contribution after 1 year. Immediate vesting)
• Generous Medical Insurance Stipend; increases with tenure
• Off-the-Job Accident Policy ($40,000 coverage + wellness benefits)
• Protective Footwear Reimbursement
• OSHA
  10 and Forklift Certification provided

If you’re passionate about making a difference—both in your community and in people’s lives—this is the job for you.

Apply here on Linked In and/or submit your resume to Rob Guardiola: rguardiola