Regional Operations & Subcontractor Coordinator

Winter Services, LLC; Milwaukee (WI); On-site; USD 55,000 - 90,000; Full time

Job summary

Winter Services, LLC is seeking a Regional Operations & Subcontractor Coordinator to plan, coordinate, and monitor commercial landscape and snow/ice operations within the GroundMasters National Division. You will work with Account Managers, subcontractors, customers, and internal teams to staff, schedule, document, and bill services per contracts and budgets.

The role emphasizes building a qualified subcontractor network, readiness for peak seasons, service quality, storm response, compliance,

Qualifications

• Knowledge of commercial landscape and snow/ice management.
• Experience working with subcontractors, vendors, service partners, or customers.
• Excellent organizational, communication, and problem-solving skills.
• Ability to manage multiple priorities in a fast-paced, changing environment.
• Strong relationship-building and negotiation skills.
• Proficiency with Microsoft Office (Excel, Word, Outlook).
• willingness to work evenings, weekends, and peak-season hours as needed.

Responsibilities

• Coordinate day-to-day landscape and snow/ice operations for assigned properties and regions.
• Ensure adequate subcontractor coverage, staffing, equipment, and resources.
• Monitor service quality, budgets, and compliance with contracts.
• Build and maintain a regional subcontractor network and manage documentation.
• Coordinate and monitor preseason/postseason readiness and storm response.
• Support billing, documentation, and administration tasks.

Skills

Subcontractor management

Communication

Problem-solving

Excel/Office proficiency

Negotiation

Account management

Education

Bachelor's degree or equivalent

Tools

CRM

GPS/photo documentation

Field-service software

Job description

POSITION SUMMARY

The Regional Operations & Subcontractor Coordinator is responsible for planning, coordinating, and monitoring commercial landscape and snow and ice operations for the GroundMasters National Division within an assigned region. This position works closely with Account Managers, subcontractors, customers, vendors, and internal teams to ensure services are properly staffed, scheduled, performed, documented, and billed according to customer expectations, contractual requirements, company standards, and budgetary guidelines. The Coordinator is responsible for building and maintaining a qualified subcontractor network, regional preseason and postseason readiness, service quality, storm response, compliance, billing support, and resolution of operational issues. This position requires strong organization, communication, problem-solving, negotiation and relationship-building skills, as well as flexibility during peak seasons and active weather events.

KEY DUTIES & RESPONSIBILITIES

Regional Operations

• 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.

Subcontractor Management

• 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.

Snow & Ice Operations

• 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 elevate 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.

Landscape Operations & Customer Support

• 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.

Billing, Technology & Administration

• 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.

QUALIFICATIONS

Required

• 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.
• Strong attention to detail and accountability.
• 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.

Preferred

• Bachelor's degree or equivalent combination of education and relevant experience.
• Experience in commercial landscape, snow and ice management, property services, facilities management, or a related industry.
• Experience with field-service, GPS/photo documentation, CRM, or operational management software.
• Experience with subcontractor billing, invoice reconciliation, or service auditing.
• Knowledge of landscape enhancement sales and processes.

CORE COMPETENCIES

• Operational coordination and leadership
• Subcontractor and relationship management
• Communication and negotiation
• Problem-solving and decision-making
• Organization and time management
• Customer service
• Attention to detail
• Accountability
• Adaptability
• Technology proficiency

PHYSICAL DEMANDS & WORKING CONDITIONS

• Extended periods of computer and telephone use.
• Availability for nights, weekends, holidays, and overnight hours during significant weather events as needed.
• Occasional travel to offices, customer properties, subcontractor locations, or other work sites.
• Occasional outdoor site visits and exposure to varying weather conditions.
• Occasional lifting of objects weighing up to 50 pounds.
• Occasional stoop, kneel, crouch, reach, or grasp activities associated with property checks.

Reasonable accommodations may be made to enable individuals with disabilities to perform the essential functions of the position.

EQUAL EMPLOYMENT OPPORTUNITY

Winter Services is an equal opportunity employer that takes pride in creating a diverse and inclusive workplace. The company complies with all applicable federal, state, and local fair employment practices law. Winter Services strictly prohibits and does not tolerate discrimination against employees, applicants, or any other covered persons because of age, race, religion, color, creed, disability, familial status, sex (including pregnancy, childbirth, breastfeeding, and related medical conditions), sexual orientation, gender, gender expression, gender identity, genetic information, marital status, national origin, ancestry, veteran or military status, or any other characteristic protected by federal, state, or local law.