Job Description

Winkler Tree & Lawn Care |Bellwood, IL (Chicagoland) | Full time, on-site

Run a fifty-year-old Chicago institution as your own business, with a national platform behind you and relocation support to get you here.

Since 1975, Winkler Tree & Lawn Care has grown into one of the largest tree and lawn care companies in Chicagoland, and the work is what built it. Our crews have climbed, pruned, treated and saved the oaks and elms that give these neighborhoods their character, which is how Winkler became the first tree care company in Illinois to earn national accreditation from the Tree Care Industry Association, a standard fewer than 300 companies in the country meet. Today seven ISA Certified Arborists with more than a hundred years between them lead crews across Cook, DuPage and Lake Counties, pruning better than fifteen thousand trees a season and serving over twenty municipalities alongside a residential book in the finest addresses in the market, where clients pay for craftsmanship and come back season after season. That reputation is Winkler’s own, earned here over fifty years, and Perennial Services Group backs it with the resources of a national family of nearly 40 local, founder-led home services brands.

As General Manager, the business is yours to run. You own the P&L and every lever that moves it: pricing, the wage structure, crew configuration, bid strategy, the sales plan and the hiring. You build the plan, you make the calls, and the results are yours. The room to grow is real, because Chicagoland is the third largest metro market in the country and the Winkler name already opens doors in it. You will report to a regional president who knows this business at ground level, which gives you a sounding board who has actually done the job. And because every company in this family runs its own way, Winkler will run your way, backed by central support teams and a peer group of general managers you can call on anytime you want to throw an idea around before you run with it.

Who This Role Is Built For

• Five to seven years as a General Manager, Branch Manager, District Manager or equivalent leader with full P&L accountability in a customer-facing, entrepreneurial business
• A proven track record recruiting, developing and retaining skilled trade labor in a wage-competitive market where good crews have options
• Demonstrated results building a high caliber residential client experience, where craftsmanship and straight communication are what drive retention
• Green industry experience strongly preferred: tree care, arboriculture, plant health care, lawn care or landscape. ISA Certified Arborist preferred, or the willingness to earn it. A strong operator from an adjacent home services trade can translate.
• A sales leader as much as an operator. You have coached sellers, set targets, and grown a book through the people you developed.
• A leader who runs on data. You read your operating numbers daily, act the same day, and have taught a team to do the same.
• A visible, hands-on leader. You are with your people where the work happens, you are direct with them including when the message is hard, and you like having senior leadership close enough to help.
• Master’s or Bachelor’s degree, or equivalent operating experience

What You’ll Own

1. The Business

• Full accountability for revenue, margin, labor and growth. You build the budget and you deliver it, with an owner’s mindset that balances this season against the next five.
• Daily command of production volume, revenue per hour across both municipal and non-municipal work, crew efficiency and avoidable operational errors
• Pricing, renewals and bid strategy, including the 2026 to 2027 winter season bid book, volume targets and staffing levels

2. The Labor Model

• Own the wage structure, incentive bonus program and recruiting strategy, including referral and signing bonuses, that win experienced production arborists in the Chicago market
• Set crew configuration and the staffing plan, and plan deliberately for the busy season, the municipal season and the winter
• Grow your own talent through training, certification and cross-training, and build the bench you will promote from

3. The Team

• Lead and develop an Assistant General Manager, Operations Manager, Plant Health Care Manager, Turf Care Supervisor, Fleet Manager and the sales team
• Coach your leaders through regular, documented development conversations, address underperformance directly, and keep building the culture that makes good crews stay
• Lead where the work happens: at the shop for crew rollout, on job sites, and in the office and available to your people

4. Clients, Growth and Standards

• Lead, train and develop the sales team to budget, and drive client retention through plant health care and turf renewal season
• Own the escalated client relationships personally and make the call when an account needs to be restructured
• Hold the business to ANSI and industry standards, where safety, training and compliance are non-negotiable and our national accreditation is something we re-earn. Work with the leadership team and the other Chicago brands to grow across service lines.

How Success Is Measured

Your first ninety days are spent with your crews, on their routes, and in front of the clients who have been with Winkler longest, so the read you build on this business is your own. By the end of your first season it shows up in the numbers: daily production and revenue per hour at target, the sales team tracking to budget, and the winter bid book filled on plan. A year in, the business is bigger and more profitable than the one you took over, and the bench you built is what made that possible: more certified arborists and more crew leaders ready for their next step than the day you walked in, and a team that is steadier for how you led it.

Compensation and Benefits

Base salary ranges from $130,000 to $150,000 a year, based on experience and scope, plus annual performance bonus eligibility tied to the results you deliver.

Beyond the paycheck, the benefits are built to take care of you:

• Health covered the way you actually use it. Medical, dental and vision through Cigna, with three medical plans to choose from, plus HSA and FSA options.
• A 401(k) match worth taking. Safe Harbor 401(k) matching up to 4 percent, with immediate 100 percent vesting. Roth or traditional, your call.
• A safety net for the unexpected. Optional life and AD&D, short- and long-term disability, and legal coverage at group rates.
• Real support for real life. A free, confidential assistance program for you and your whole household, plus optional pet insurance.
• Time to live. Paid time off and company holidays.
• Help getting here. Relocation support is available for the right candidate moving into the Chicago market.
• Room to keep building. We pay for certifications, licenses and continuing education including ISA credentials, and we grow leaders into bigger seats across a national family of brands.

Come Build the Next Fifty Years

A team worth leading and a whole Chicago market to grow. If you have carried a P&L and know how to win and keep good people, this is the seat where the decisions are yours.

Apply today and let’s talk!

Applicants must be authorized to work in the United States without the need for employer visa sponsorship, now or in the future. Winkler Tree & Lawn Care is a partner company of Perennial Services Group, which participates in E-Verify and confirms the employment eligibility of all newly hired employees. Employment is contingent on a satisfactory background check and an acceptable driving record.

Winkler Tree & Lawn Care and Perennial Services Group are equal opportunity employers. We consider all qualified applicants without regard to race, color, religion, sex, national origin, age, disability, genetic information, or any other status protected by law.

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