Lawn Care Crew Leader

Wintergreen Site Management — West Bend, WI
Pay: $22–$30/hour, based on experience and leadership ability
Job Type: Full-time, year-round
Schedule: Monday–Thursday, 7:00 AM–5:00 PM during lawn care season
Location: West Bend, WI and surrounding service areas

Immediate Opening — Hiring Now

Wintergreen Site Management is hiring an experienced Commercial Lawn Care & Snow Operations Crew Leader to lead our commercial and residential lawn care operation.

We are looking to bring the right person on immediately for a two-week training and transition period. This time will be used to learn our routes, customer properties, equipment, quality standards, operating procedures, and daily expectations before taking full ownership of the lawn care crew and route.

This is a hands-on, year-round leadership position. Lawn care responsibilities take place during the growing season, followed by full-time snow and ice management from November through April. There are no planned seasonal layoffs.

About Wintergreen

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

We serve commercial properties, HOAs, and residential customers throughout West Bend and surrounding communities. As a small, growing company, reliability, ownership, communication, and attention to detail make a direct difference.

Lawn Care Schedule

• Monday–Thursday, 7:00 AM–5:00 PM
• Four 10-hour days during the lawn care season
• Fridays and occasional weekends may be used as rain make-up days
• Weather and route completion may require schedule flexibility

What You’ll Do:

Route Production

• Lead a commercial and residential weekly mowing route
• Operate commercial zero-turn and stand-on mowers
• Complete weekly mowing to Wintergreen quality standards
• Perform string trimming and bi-weekly edging
• Blow off sidewalks, driveways, curbs, entrances, and hard surfaces
• Complete minor weeding when needed
• Keep the crew moving efficiently while protecting quality
• Complete assigned properties on time and communicate delays promptly

Crew Leadership

• Lead daily crew start-up and task assignments
• Set expectations for quality, pace, safety, and professionalism
• Train and coach crew members in mowing, trimming, edging, cleanup, and equipment care
• Monitor productivity and correct problems in the field
• Lead by example with a positive attitude and strong work ethic
• Communicate property concerns, customer requests, and equipment issues
• Build a reliable, respectful, and accountable crew culture

Quality Control

• Inspect each property before leaving
• Identify missed areas, uneven mowing, poor trimming, skipped edging, clippings, and debris
• Protect buildings, vehicles, landscaping, fences, irrigation, and customer property
• Correct small issues immediately to prevent callbacks
• Maintain consistent standards across every property on the route

Equipment and Truck Responsibilities

• Safely operate trucks, trailers, mowers, trimmers, blowers, and edgers
• Complete daily equipment inspections
• Load, unload, fuel, clean, and secure equipment properly
• Perform basic mower maintenance
• Sharpen and monitor mower blades
• Report damaged, unsafe, or malfunctioning equipment immediately
• Keep the truck, trailer, and equipment organized and ready for work

Winter Snow Operations

From November through April, this position will support Wintergreen’s snow and ice management operation.

Responsibilities may include:

• Operating a plow truck
• Operating a skid steer with plow or snow equipment
• Plowing commercial and residential properties
• Salting and de-icing
• Clearing sidewalks, entrances, and walkways
• Supporting snow removal crews
• Monitoring properties during and after snow events
• Refueling, cleaning, and checking equipment
• Communicating site conditions and completion status

Snow operations are weather-driven and may require availability during early mornings, overnight hours, weekends, holidays, and extended shifts. Team members assigned to snow removal must be available for winter operations around the clock during snow and ice events.

Required Experience and Qualifications

• Proven commercial mowing experience
• Experience operating commercial zero-turn or stand-on mowers
• Ability to lead a route and complete work on schedule
• Ability to direct and coach crew members
• Valid driver’s license and clean driving record
• Reliable transportation
• Ability to operate or learn to operate plow trucks and skid steers
• Ability to work outdoors in Wisconsin weather
• Ability to lift 50 pounds
• Strong attention to detail
• Good communication and problem-solving skills
• Willingness to follow Wintergreen SOPs, safety standards, and quality expectations

The Right Person Will

• Show up on time and be dependable every day
• Take ownership of the route and crew results
• Complete work correctly instead of cutting corners
• Notice details others miss
• Maintain a steady pace while protecting quality
• Treat equipment, teammates, and customer property with respect
• Communicate problems early
• Stay calm and productive when conditions change
• Accept coaching and continue improving
• Take pride in representing Wintergreen professionally

This Position Is Not a Good Fit If You

• Are frequently late or unreliable
• Do not have commercial mowing experience
• Cut corners on quality
• Are careless with equipment or customer property
• Do not want leadership responsibility
• Resist coaching or company procedures
• Have poor communication habits
• Are unwilling to participate in winter snow operations

Compensation and Benefits

• $22–$30 per hour, based on experience and ability
• Full-time, year-round employment
• No planned seasonal layoffs
• Paid training
• Paid time off
• Company-provided apparel
• Opportunities for advancement
• Leadership growth opportunities
• Winter snow and storm-work opportunities

How to Apply

Apply through Indeed to begin the hiring process.

We are actively interviewing qualified candidates and will move quickly for the right person. Qualified candidates will complete a brief phone screening and may be invited for an in-person interview or working interview.

Pay: $22.00 - $30.00 per hour

Benefits:

• Opportunities for advancement
• Paid time off
• Vision insurance

Experience:

• Mowing: 2 years (Preferred)

License/Certification:

• drivers license (Required)

Work Location: In person

Salary : $22 - $30