Skid Steer Operator CDL

Compensation $30.00 - $40.00/hour

Job Description

🌲 Power Through the Woods - Join Whitetail Forestry as a Skilled Skid Steer Operator with CDL! 🌲

Skid Steer Operator with CDL

Whitetail Forestry

Forestry/Land Clearing

Milton, WI

Whitetail Forestry is seeking a reliable and independent Skid Steer Operator with a CDL to join our hands‑on field operations team. This full‑time position is ideal for someone who enjoys working outdoors, takes pride in equipment care, and thrives in solo work environments. You’ll operate forestry equipment for land clearing, tree and brush removal, and site prep while maintaining a customer‑friendly attitude at every job site.

Whitetail Forestry is a locally trusted land and forestry service provider based in Milton, WI. We specialize in environmentally responsible clearing and forestry solutions for residential, commercial, and government clients. At Whitetail, we believe in keeping things simple and solid — no drama, no micromanagement. Our small team values loyalty, clear communication, and quality workmanship. With a loyal owner who has your back and a crew that keeps things moving efficiently, Whitetail Forestry offers a professional and low‑stress work environment where your independence and reliability are respected.

Learn more at

• Operate skid steers and forestry attachments safely and efficiently
• Load and unload equipment at job sites
• Execute land clearing, tree removal, and brush management tasks
• Conduct regular maintenance checks and basic upkeep of equipment
• Work independently with minimal supervision after morning check‑in
• Communicate professionally with customers on‑site as needed
• Use chainsaws occasionally for supplementary clearing

• MUST have a valid CDL and a clean driving record
• 1+ year of Skid Steer Operation Experience
• Ability to operate forestry tools, including skid steers and chainsaws
• Strong work ethic and ability to manage your time in the field independently
• Comfortable working outdoors in varying weather conditions
• Ability to safely lift, load, and perform physical labor as needed
• Paid Overtime for hours over 40/week
• Holiday time off
• Respectful, low‑drama work culture
• No micromanagement — enjoy independent, focused workdays
• Modern, well‑maintained equipment
• Future eligibility for paid vacation/holidays after one year based on performance and reliability

• Full‑Time — Monday to Friday
• Overtime opportunities available

• Milton, WI and surrounding regions
• Primarily local work with occasional travel to job sites in the region

We are proud to be an Equal Opportunity Employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, disability, protected veteran status, or any other legally protected status.

A background check will be completed as part of the onboarding process, in compliance with applicable laws.