Senior Manager

About the Role:

Custom Caretaking & Landscaping is seeking an experienced Senior Manager to join our leadership team. This is a mid-to-senior-level operations hire designed to take ownership of day-to-day field and office operations. The right candidate will have a clear path to grow into a head of operations or president-level role within the company.

Key Responsibilities

Field Operations

• Dispatch crews each morning and plan daily tasks
• Provide field supervision and oversee project execution from start to finish
• Ensure all equipment and vehicles are properly maintained and ready for any task
• Troubleshoot problems with jobs and employees in the field
• Oversee all materials and tools needed for each job
• Oversee estimating and bidding to ensure accurate job costing on labor, materials, and equipment
• Monitor job-level gross margin and report performance to upper management
• Manage seasonal workforce planning including spring ramp-up and winter/snow removal readiness
• Ensure OSHA safety compliance at all sites
• Assist with purchasing approvals and vendor pricing

Customer & Business Development

• Work with customers on projects and client samples
• Meet with prospective clients to pursue new business opportunities
• Maintain a courteous, outgoing, and customer-focused approach at all times

Office & Billing

• Guide the office team through job-to-job billing processes
• Support coordination between field crews and the office

Leadership & Team Management

• Lead, motivate, and manage field crews with professionalism and respect
• Conduct performance reviews and support employee retention
• Take on increasing operational responsibility over time
• Serve as a key part of the company’s long-term leadership succession plan

What We’re Looking For

• Mid- to senior-level experience in field-based service operations (landscaping, caretaking, outdoor services, or similar industry strongly preferred)
• Early riser with strong organizational and planning skills — able to run a tight morning dispatch and set daily priorities
• Strong interpersonal skills — able to earn the respect of field crews while building relationships with customers
• Proven ability to work independently, solve problems quickly, and make sound decisions in the field
• Growth mindset — interested in taking on greater responsibility and potentially succeeding into a president or COO-type role
• Outgoing, courteous, and professional in all interactions

Job Details

Job Type: Full-Time

Location: Arbor Vitae, Wisconsin

Compensation: $110-140k total compensation

Pay: $52.88 - $67.31 per hour

Benefits:

• Relocation assistance

Work Location: In person