Lawn Care Apprentice / Technician — Year-Round Growth Opportunity

Wintergreen Site Management — West Bend, WI

Pay: $18–$25.50/hour, based on experience and ability Job Type: Full-time seasonal with year-round work opportunity Schedule: Monday–Thursday, four 10-hour days during lawn care season Location: West Bend, WI and surrounding service areas

Build a Career in Lawn Care, Landscaping, and Snow Management

Wintergreen Site Management is hiring a Lawn Care Apprentice / Technician to join our lawn care crew.

This is not just a seasonal mowing job. We are looking for someone who wants to learn, work hard, follow systems, and grow into a more valuable role with our company over time.

During the lawn care season, you’ll work under experienced leadership and learn how we complete weekly mowing routes with quality, safety, consistency, and attention to detail.

During the winter season, we provide snow plowing, snow removal, salting, sidewalk clearing, and ice management. For the right person, there are opportunities for year-round work in roles such as plow truck driver, skid steer operator, sidewalk crew member, and salting operator.

Our ideal candidate is someone who wants to build a future with Wintergreen — not just work here for a few months.

About Wintergreen

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

We serve commercial, HOA, and residential 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, take pride in your work, learn our SOPs, and bring a good attitude, there is real opportunity to grow with us.

Schedule

Our lawn care route is built around a four-day workweek:

Monday–Thursday: 7:00 AM–5:00 PM

In a typical week, once the weekly route is completed, the workweek is done. This gives the team Friday, Saturday, and Sunday off most weeks.

Because lawn care is weather-dependent, Fridays and occasional weekends may be used as rain make-up days when weather prevents us from completing the route Monday–Thursday.

Winter snow work is weather-based and requires flexibility during snow and ice events.

What You’ll Do

During lawn care season, you’ll help complete weekly mowing and property maintenance routes.

Responsibilities include

• Mowing commercial, HOA, and residential properties
• Operating stand-on commercial zero-turn mowers safely and efficiently
• Performing professional trimming and edging
• Blowing off sidewalks, driveways, curbs, and hard surfaces
• Loading, unloading, fueling, and cleaning equipment
• Helping with basic equipment care and safety checks
• Reporting damaged, unsafe, or malfunctioning equipment
• Communicating issues with the Crew Leader
• Following Wintergreen’s SOPs, systems, safety standards, and quality expectations

During winter, qualified team members may have opportunities to help with

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

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
• Growth-minded and interested in year-round opportunity
• Detail-oriented and proud of finished results
• Safe and respectful around equipment, trucks, trailers, and customer property
• Comfortable working outdoors in Wisconsin weather
• Able to work hard physically and keep pace with a route
• Positive, respectful, and easy to work with

Some lawn care, landscaping, snow removal, or outdoor work experience is preferred, but we are willing to train the right person if they have the right attitude, work ethic, and desire to grow.

Growth Path

This role is designed as a growth opportunity

Lawn Care Apprentice → Lawn Care Technician → Winter Operations Team Member → Assistant Crew Leader → Crew Leader

For the right person, the long-term opportunity is to lead a route, crew, or operational role as Wintergreen continues to grow.

As your skill, reliability, leadership, and responsibility increase, so does your opportunity.

Requirements

• Valid driver’s license
• Clean driving record
• Reliable transportation
• Ability to lift 50+ lbs
• Ability to work outdoors in varying weather conditions
• Ability to safely operate or learn to operate commercial lawn care and snow equipment
• Willingness to follow company SOPs, standards, and safety procedures
• Flexibility for weather-related schedule changes during lawn care and snow seasons

Compensation & Benefits

• $18–$25.50/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

This Job Is a Good Fit If You…

• Want more than a short-term seasonal job
• Take pride in doing quality work
• Are willing to be trained and coached
• Care about showing up, working safely, and improving
• Want to become more valuable over time

This Job Is Not for You If…

• You are unreliable or frequently late
• You are careless with equipment
• You do not want to be coached
• You do not want to follow SOPs
• You cut corners on quality
• You bring a negative attitude to the crew
• You are only looking for short-term work with no interest in growth

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 - $25.50 per hour

Benefits

• Opportunities for advancement
• Paid time off
• Paid training

Work Location: In person