Director of Landscaping Maintenance & Snow Operations

About Us

We are a growing, full-service landscape company delivering high-quality design/build, maintenance, enhancement, projects and snow & ice services across the Chicago area. We're building a professional, systems-driven organization where strong leaders have the tools, autonomy, and support to win. This is a key leadership role on our team.

The Opportunity

This is a senior leadership role accountable for the performance of the entire division — maintenance, enhancement, projects and snow. You'll lead and develop your supervisors, account managers, and customer service team, own the systems and standards that drive quality and profitability through every season, and bring the hands-on credibility that earns respect in the field when the work demands it.

If you've grown through roles like Branch Manager or Operations Manager and are ready to own a division end-to-end — running a profitable operation, developing your team into high performers, and being the person the whole division counts on — we want to talk to you.

What You'll OwnLead & Develop the Team

• Lead, coach, and develop your crew supervisors (who direct the crew leaders and field teams), your account managers, and your customer service team
• Run consistent one-on-ones and team meetings; set clear expectations and follow through
• Build a strong leadership bench — hire, onboard, train, and evaluate your direct reports and support their development of the teams below them
• Drive morale, retention, and a culture of accountability and pride in the work across the division

Own Division Profitability

• Hold the division accountable to its revenue and gross-margin targets
• Track job and route costing against estimates; identify and close margin gaps
• Manage labor hours, equipment utilization, and materials cost
• Partner with sales and estimating to ensure work is priced to win and to profit
• Owns and manages a personal book of accounts, including client relationship management, selling and upselling, prospecting for new business, and account retention.

Run Maintenance & Enhancement Operations

• Own routing, scheduling, and quality control across all maintenance accounts
• Ensure every property meets our quality standard, consistently and on schedule
• Grow enhancement/upsell revenue by equipping your supervisors and crews to spot opportunities and ensuring quotes are generated and followed up
• Drive client satisfaction and retention through your account management and customer service team

Lead Snow & Ice Operations (Seasonal)

• Serve as the single owner of snow operations — planning, staffing, routing, equipment readiness, and storm-event execution
• Manage on-call rosters, subcontractors, salt/materials inventory, and 24/7 event coordination
• Ensure accurate documentation, site logs, and billing for every event
• Deliver safe, reliable, on-budget service that protects client relationships

Manage by the Numbers

• Own and report your division's key metrics weekly
• Build and enforce repeatable processes for maintenance and snow operations
• Use LMN and related tools to run the business on data, not guesswork

What Success Looks Like

• The division consistently hits its revenue and gross-margin targets
• Supervisors, account managers, and crews are well-led, well-trained, and accountable
• Clients are retained and satisfied, supported by a responsive account management and customer service team
• Snow events are executed safely, on time, and on budget
• Enhancement revenue grows year over year
• The division runs smoothly and proactively, without day-to-day fires reaching ownership

What You Bring

• 5+ years in green-industry / landscape operations, including 3+ years leading teams through supervisors or managers (e.g., as a Branch Manager, Operations Manager, or Division Manager)
• Experience leading client-facing account management and/or customer service functions
• Proven experience running or co-running snow & ice operations in a Snowbelt market
• A track record of budget and gross-margin accountability
• Strong people-leadership skills — hiring, coaching, holding others accountable, and reducing turnover
• Proficiency with LMN (Landscape Management Network) for job costing, scheduling, and estimating
• Comfort managing an operation by the numbers
• Availability for 24/7 responsiveness during snow events
• Valid driver's license

Nice to Have

• Experience building or rebuilding a maintenance or snow division
• Pesticide/applicator licensing
• A calm, decisive leadership presence under pressure
• A systems-and-process mindset