Field Operations Supervisor - Landscaping & Maintenance

MILWAUKEE COMMUNITY SERVICE CORPS; Milwaukee (WI); On-site; USD 30,307 - 35,817; Full time

Benefits offered by this job

13 Paid Holidays

2 Weeks Paid Time Off

403B Retirement Plan

Medical Insurance Stipend

Accident Policy

Protective Footwear Reimbursement

OSHA10 and Forklift Certification

Job summary

A nonprofit organization in Milwaukee seeks a Field Operations Supervisor to lead landscaping crews and mentor trainees. Responsibilities include project supervision, equipment operation, and ensuring safety protocols. Candidates should have strong communication and leadership skills, and a high school diploma. This role offers competitive pay and various benefits, focusing on community development and empowerment.

Qualifications

• Valid Wisconsin driver's license and insurable driving record.
• Reliable transportation to/from MCSC's Milwaukee office.
• Experience mentoring or training others is preferred.

Responsibilities

• Lead and supervise crews on various landscaping projects.
• Train and mentor crew members.
• Ensure safety by enforcing OSHA protocols and leading by example.
• Operate and maintain landscaping tools and equipment.

Skills

Strong communication skills

Leadership skills

Experience with landscaping tools

Ability to lift 50 pounds

Education

High school diploma or equivalent

Tools

Mowers

Trimmers

Snowplows

Wood chippers

Job description

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.

What This Job Is All About

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.

What You’ll Be Doing – Day to Day

• 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

What You Bring to the Table

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

Benefits & Perks

• 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
• OSHA10 and Forklift Certification provided

Join Us

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 LinkedIn and/or submit your resume to Rob Guardiola: [e-mail]