Regional Operations & Subcontractor Lead

Winter Services Inc; Milwaukee (WI); On-site; USD 65,000 - 90,000; Full time

Job summary

Winter Services Inc. in Milwaukee, WI seeks a Regional Operations & Subcontractor Coordinator to plan, coordinate, and monitor commercial landscape and snow/ice operations across a designated region.

You will collaborate with account managers, subcontractors, customers, vendors, and internal teams to ensure staffing, scheduling, service delivery, documentation, and billing meet expectations, budgets, and standards.

Qualifications

• Knowledge of commercial landscape and/or snow and ice management.
• Experience working with subcontractors, vendors, service partners, or customers.
• Excellent organizational, communication, and problem-solving skills.
• Ability to manage multiple priorities and adapt to a fast-paced, changing environment.
• Strong relationship-building, negotiation, and cold-calling skills.
• Proficiency with Microsoft Office, particularly Excel, Word, and Outlook.
• Ability and willingness to work evenings, weekends, holidays, and extended hours during peak seasons and active weather events as needed.
• Discretion and trustworthiness when handling confidential information.

Responsibilities

• Coordinate day-to-day landscape and snow/ice operations for assigned properties and service areas.
• Ensure adequate subcontractor coverage, staffing, equipment, and resources to meet customer requirements.
• Monitor service completion, quality, budgets, and compliance with scopes of work.
• Identify and resolve service issues, coverage gaps, customer concerns, and safety risks; Escalate issues when appropriate.
• Maintain accurate property, service, subcontractor, and operational information.
• Establish and follow procedures that support quality, efficiency, safety, and consistent service delivery.
• Prospect, cold call, qualify, negotiate with, and develop relationships with new and existing subcontractor partners.
• Coordinate subcontractor agreements, site assignments, scopes of work, pricing, equipment rates, and required documentation.
• Build and maintain a reliable regional subcontractor network and proactively identify coverage needs.
• Monitor subcontractor performance and address quality, responsiveness, service, and compliance issues.
• Maintain complete subcontractor files, including agreements, W-9s, Certificates of Insurance, licenses, and other required documentation.
• Conduct regular compliance audits and ensure all required documentation is current before work is performed.
• Monitor weather and coordinate preseason storm readiness, including staffing, equipment, materials, routes, and property requirements.
• During snow and ice events, monitor service execution and maintain communication with subcontractors and internal teams.
• Track service completion, timing, equipment, materials, photos, and other required documentation.
• Resolve or escape missed services, uncovered properties, equipment/staffing issues, and other storm-related concerns.
• Coordinate and monitor snow removal, hauling, salting, deicing, and other winter services as required.
• Conduct post-storm reviews and follow up on service documentation, discrepancies, and subcontractor performance.
• Coordinate and monitor recurring commercial landscape services and seasonal activities.
• Partner with Account Managers to understand customer scopes, expectations, service levels, and property-specific requirements.
• Assist with customer escalations, service recovery, inspections, and quality control.
• Identify opportunities for enhancements, additional services, and other customer needs.
• Identify and promptly communicate safety concerns, property damage, or other conditions affecting service or customer satisfaction.
• Review service documentation and subcontractor invoices for accuracy and compliance with contracted rates and approved work.
• Assist with billing reconciliation, pay questions, discrepancies, change orders, and additional services.
• Support Sitefotos and other operational systems, including setup, training, service documentation, and troubleshooting.
• Assist with preseason audits of subcontractor rates, equipment, agreements, assignments, and compliance.
• Maintain accurate files, site maps, reports, and operational records.
• Perform other administrative and special projects as assigned.

Skills

Subcontractor management

Organizational skills

Communication skills

Problem-solving

Negotiation

Cold-calling

Attention to detail

Microsoft Office (Excel, Word, Outlook

Time management

Adaptability

Education

Bachelor's degree or equivalent experience

Tools

CRM software

GPS/photo documentation

Field-service software

Operational management software

Job description

Winter Services Inc. in Milwaukee, WI seeks a Regional Operations & Subcontractor Coordinator to plan, coordinate, and monitor commercial landscape and snow/ice operations across a designated region.

You will collaborate with account managers, subcontractors, customers, vendors, and internal teams to ensure staffing, scheduling, service delivery, documentation, and billing meet expectations, budgets, and standards.