Senior Operations Manager

Company Overview: Western DuPage Landscaping is an established landscaping company that has been serving the Chicagoland area and the western suburbs for nearly 50 years. We pride ourselves on our passionate staff whose focus is on quality. We are seeking candidates who fit our core values and can grow with our team, building on our extensive history of creating landscapes that are built to last.

Senior Operations Manager

Landscape Maintenance & Snow Services

Location: Naperville, IL | Chicagoland & Western Suburbs
Employment Type: Full-Time, Year-Round

About the Role

We are seeking a proven Senior Operations Manager to lead our landscape maintenance and snow services divisions. The role provides strategic and operational leadership for the company’s landscape maintenance and snow services divisions. This role is accountable for people leadership, operational execution, financial performance, and client retention across residential and commercial portfolios. The position serves as the operational bridge between sales, field operations, snow management, and executive leadership, ensuring services are delivered safely, efficiently, and profitably while supporting long-term growth.

What You’ll Do

• Lead day-to-day operations across landscape maintenance and snow services
• Own divisional performance including revenue growth, margins, and retention
• Oversee seasonal planning, labor forecasting, and snow readiness
• Maintain executive relationships with key commercial and residential clients
• Resolve escalated service and operational issues
• Support new business development, enhancements, and contract renewals
• Lead, coach, and develop Account Managers and operational staff
• Drive process improvements, efficiency, and safety compliance

What We’re Looking For

• 5+ years in landscape maintenance or snow operations leadership
• Strong financial and operational management experience
• Proven ability to lead teams, manage clients, and drive accountability
• Experience with budgets, pricing, contracts, and margins
• Commercial snow operations experience strongly preferred
• Experience with LMN, Aspire, or similar operational software

Why Join Us

• Senior leadership visibility and influence
• Competitive salary with performance incentives
• Company vehicle and full benefits
• Long-term growth into Director or Branch Leadership roles
• Stable, well-established company with nearly 50 years in the market

Benefits:

• Company Vehicle
• Paid Vacation Days
• Health Insurance
• Dental Insurance
• Life Insurance
• Vision Insurance
• Additional Life Insurance
• 401k (after 12 months)

How to Apply: Please send your resume and a cover letter to susan@wdlinc.com

Job Type: Full-time

Pay: $55,000.00 - $85,000.00 per year

Benefits:

• 401(k)
• 401(k) matching
• Dental insurance
• Health insurance
• Health savings account
• Life insurance
• Paid time off
• Vision insurance

Application Question(s):

• Within your most recent landscape maintenance sales role, how many team members did you manage?
• Can you name plants by sight & discuss them in a conversation effectively?

(e.g., with plants, flowers, shrubs, trees, etc.)

• Which of the following software tools are you familiar with?

MS Outlook, Word & Excel
AutoCAD and/or SketchUp
Adobe Suite
LMN and/or Aspire
Any others relevant to this role?

Experience:

• landscape maintenance sales: 3 years (Required)
• Landscape maintenance: 3 years (Required)

Language:

• English & Spanish (Preferred)

Ability to Commute:

• Naperville, IL 60563 (Required)

Work Location: In person