Landscape Maintenance / Softscape Apprentice — Year-Round Growth Opportunity

Wintergreen Site Management — West Bend, WI

Pay: $18–$27/hour, based on experience and ability Job Type: Full-time seasonal with year-round work opportunity Schedule: Tuesday–Friday during training; possible Monday–Friday after onboarding Location: West Bend, WI and surrounding service areas

Build a Career in Landscaping — Not Just a Labor Job

Wintergreen Site Management is hiring a Landscape Maintenance / Softscape Apprentice to join our team.

This role is for someone who wants to work outdoors, learn the landscape trade, and grow with a company that is putting real SOPs, systems, standards, and expectations in place.

This is not a sit-on-a-mower-all-day position. This role focuses on landscape maintenance, softscape work, property improvements, planting, mulch, stone, pruning, grading, seeding, and small enhancement projects.

We are looking for someone reliable, coachable, safe, detail-oriented, and willing to learn the Wintergreen way of doing things.

For the right person, this can become a year-round opportunity with growth in landscaping, snow removal, salting, equipment operation, and future crew leadership.

About Wintergreen

Wintergreen Site Management is a growing lawn care, landscaping, and snow removal company based in West Bend, WI.

We serve residential, commercial, and HOA properties throughout West Bend and surrounding communities. We are a small but growing company, which means your effort, attitude, reliability, and attention to detail matter here.

If you show up daily, work hard, follow our SOPs, take pride in your work, and bring a good attitude, there is real opportunity to grow with us.

Schedule

This position typically starts Tuesday–Friday during the training period, with 8–10 hour days and approximately 32–40+ hours per week, depending on workload, weather, and project needs.

After onboarding and training, the schedule may transition to Monday–Friday depending on...