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 workload, weather, and the employee’s ability to work independently.

Once trained, Mondays may include independent landscape maintenance and detail work at established properties while our mowing crew completes large sites.

What You’ll Do

You’ll help with landscape maintenance, softscape installations, and property improvement projects.

Work may include

• Planting trees, shrubs, perennials, and annuals
• Creating or renovating landscape beds
• Installing mulch, stone, and landscape fabric
• Tree pruning, shrub trimming, hand weeding, and bed cleanup
• Dirt work, grading, seed, and straw installation
• Tear-out and replacement work
• General landscape maintenance and enhancement projects
• Light hardscape support such as small paver patios, minor retaining walls, and prep work
• Loading, unloading, and moving materials
• Keeping jobsites clean, organized, and professional
• Following Wintergreen’s SOPs, safety standards, and quality expectations

This work is physical, fast-paced, and detail-oriented. We need someone who can work hard, stay focused, and take pride in how the finished job looks.

Fall and Winter Opportunity

Wintergreen also provides professional snow and ice management services.

For the right team member, fall and winter opportunities may include

• Snow plowing
• Skid steer operation
• Sidewalk snow removal
• Salting and ice management
• Snow removal support

Our ideal candidate is someone who wants to become a valuable year-round team member, not just work during the summer.

Who We’re Looking For

We are looking for someone who is

• Reliable and consistent
• Willing to show up daily and be counted on
• Coachable and willing to learn our SOPs
• Able to work at a fast pace without cutting corners
• Detail-oriented and proud of finished results
• Safe around tools, equipment, trucks, trailers, and customer property
• Comfortable working outdoors in Wisconsin weather
• Able to lift, carry, dig, rake, shovel, and move materials
• Positive, respectful, and easy to work with
• Interested in learning the trade and growing over time

Experience is helpful, but attitude, effort, safety, and coachability matter most.

Growth Path

This role is designed as a growth opportunity

Landscape Maintenance Apprentice → Landscape Technician → Winter Operations Team Member → Assistant Crew Leader → Crew Leader

For the right person, the long-term opportunity is to become someone who can help lead work, train others, operate equipment, and take ownership of projects as Wintergreen continues to grow.

Requirements

• Valid driver’s license preferred
• Reliable transportation
• Ability to lift 50+ lbs
• Ability to work outdoors in varying weather conditions
• Ability to safely use or learn to use landscape tools and equipment
• Willingness to follow company SOPs, standards, and safety procedures
• Flexibility for weather-related schedule changes during landscape and snow seasons

Compensation & Benefits

• $18–$27/hour, based on experience and ability
• Paid on-the-job training
• Paid time off
• Seasonal bonus opportunities
• Company-provided apparel
• Opportunities for advancement
• Year-round work opportunity
• Snow season opportunities for qualified team members

What We Expect

At Wintergreen, we expect our team members to

• Show up consistently and communicate clearly
• Work safely around tools, equipment, trucks, trailers, and customer property
• Follow SOPs and be open to coaching
• Work with effort, urgency, and attention to detail
• Take pride in clean, professional results
• Bring a positive attitude to the crew
• Be interested in learning and growing over time

How to Apply

Apply through Indeed to begin the process.

Qualified candidates will complete a brief phone screening and may be invited for an in-person interview.

Pay: $18.00 - $27.00 per hour

Benefits

• On-the-job training
• Opportunities for advancement
• Paid time off

Work Location: In person