Crew Lead

Umbrella Property Services is hiring a Crew Lead in Mokena, IL to run a two-person landscape maintenance crew across our commercial route in the Chicagoland area. Pay is $20 to $25 per hour on W-2 or $22 to $27 per hour on 1099, your choice. You will be the senior person on the truck, setting the pace, calling the shots on quality, and making sure every property looks right before you pull off.

Who You Are

• You take pride in being the senior person on the truck, the one your crew looks to for the pace and the standard.
• You believe a property is not finished until everything looks right at the curb.
• You love the kind of leadership that gets done by example, not by lecturing.
• You are the kind of person who can run a clean lawn route in summer and confidently plow a commercial site in a winter storm.
• You are friendly and professional with customers, and reliable with the crew behind you.
• You bring prior experience leading landscape crews, snow plowing experience, comfort towing 20-foot trailers, and a valid driver’s license.

Who We Are

• Umbrella Property Services provides dependable property services across Chicago and the wider Chicagoland area.
• We support commercial properties with coordinated service across multiple operational categories.
• We help clients reduce vendor complexity, maintain consistent standards, and protect long-term property value.
• We run year-round, with landscape maintenance through the warm season and snow operations through winter.
• We are a growing company that values teammates who lead with quality workmanship and reliability.

What You Will Do Each Day

• Lead and coordinate a small landscape crew across assigned commercial properties.
• Oversee lawn maintenance, shrub and tree trimming, and bed and mulch installation.
• Run fertilization and turf care applications on schedule.
• Manage spring and fall cleanups across the route.
• Take on snow plowing, salting, and winter site management when the season turns.
• Document work, photos, and site notes using our company systems.

Why You Will Love Working Here

• Pay of $20 to $25 per hour on W-2, or $22 to $27 per hour on 1099, based on your preferred employment structure.
• Full-time onsite Crew Lead role based in Mokena, IL, with travel to commercial properties across the Chicagoland area.
• Year-round work, with landscape maintenance in the warm season and snow operations through winter.
• Health insurance and paid time off.

At Umbrella Property Services, we take pride in maintaining high standards — not just for our clients, but for our team. We believe in clear expectations, strong leadership, and creating an environment where dependable professionals can thrive.