Landscaping Crew Lead

Date Posted: September 22, 2025
Pay: $25.00 – $30.00 per hour (DOE, higher potential for the right candidate)

Job Description

Woodridge Landscapes is seeking a Maintenance Crew Lead to oversee year-round landscape maintenance operations. This role is ideal for someone who enjoys hands-on outdoor work, takes pride in quality results, and can lead a small crew with reliability and professionalism.

As a Crew Lead, you’ll balance working alongside your team with directing tasks, maintaining schedules, and ensuring safety and efficiency on every job. For the right candidate, there is also potential to transition into a salaried leadership role.

What You’ll Do

• Lead and work with a crew to complete weekly lawn maintenance: mowing, edging, trimming, and blowing
• Oversee seasonal cleanups, planting beds, mulch installs, and small landscape repairs
• Operate and train others on zero-turn mowers, trimmers, blowers, and other equipment
• Maintain trucks, trailers, and equipment; report repairs/needs promptly
• Perform occasional maintenance on equipment to keep it in good working order
• Assist with hardscape production from time to time (e.g., paver installs, small construction tasks)
• Communicate with management on progress, issues, and scheduling needs

What We Offer

• $25–30/hr DOE + overtime opportunities (higher potential for the right candidate)
• Year-round, steady hours (not just seasonal)
• Bi-weekly pay (direct deposit)
• Company-provided tools, PPE, and uniform
• Paid training and leadership development
• Up to 1 week paid time off after 1 year of full-time employment
• Clear path to advancement — including potential salary role for strong performers

Company Culture

Family-owned and fast-growing. We value craftsmanship, teamwork, and respect. At Woodridge, you’re not just a number — your work and ideas directly shape our reputation.

Work-Life Balance

• Monday–Friday with occasional Saturdays in peak season
• Early, consistent start times and structured days
• Local projects (no overnights)
• Efficient planning so crews and managers get home on time

Why This Role Matters

Your leadership sets the tone for every project—driving crew performance, client satisfaction, and the quality that defines Woodridge.

Our Core Values

• Quality Craftsmanship – Every project reflects our reputation
• Clear Communication – Open, timely communication with clients and crews
• People First – We value and support our employees
• Quality Over Quantity – Do it right, not just fast

You Should Have

• Prior landscape maintenance experience (leadership experience preferred)
• Valid driver’s license and reliable transportation
• Ability to lift 50+ lbs and work outdoors in all weather
• Strong leadership, communication, and organizational skills
• Willingness to complete a pre-employment background/drug screen (contingent)

Schedule

• Job Type: Full-time
• Schedule: 10-hour shifts, Monday–Friday, with occasional Saturdays during peak season
• Shop Location: North Prairie, WI
• Service Area: Mukwonago, Sussex, South Milwaukee, and nearby suburbs

How to Apply (Fastest)

• Email resume or quick note to David@woodridgelandscapes.com

(Subject: Crew Lead Application) — or

• Apply via Indeed/Zip with 1-click

We encourage applicants with diverse backgrounds and those with prior convictions to apply.

Work Location: In person (North Prairie, WI)

Job Type: Full-time

Pay: $25.00 - $30.00 per hour

Expected hours: 40 – 50 per week

Benefits:

• Paid time off

Experience:

• Crew management: 3 years (Required)

License/Certification:

• Driver's License (Required)

Ability to Commute:

• Waukesha, WI 53186 (Required)

Work Location: In person