Vice President of Operations

Winter Services • Milwaukee, WI

1d

About The Position

The Vice President of Operations leads operational strategy, consistency of execution, efficiency, and growth, while overseeing multi-branch operations performing multiple services (maintenance, construction, snow). This role will manage large budgets/teams, ensure quality & safety, drive KPIs, mentor district leaders and integrate acquisitions while focusing on the execution of high-level business plans to achieve financial goals. Scope: Manages/leads multiple districts, not just single sites. Focus: Strategic vision, process optimization, and cross-functional leadership. Impact: Drives revenue, profitability, and company-wide operational excellence.

Requirements

• Bachelor’s degree in Business, Landscape Management, Horticulture, or related field.
• Extensive (10-15+ years) of operational leadership experience in the landscaping and snow industry, preferably with multi-branch or regional responsibility.
• Strong understanding of landscape maintenance, enhancements, and construction operations at scale.
• Proven track record of managing large field teams, production crews, and support staff across multiple locations in both a landscaping and snow environment.
• Strong financial acumen and KPI management with experience in forecasting, budgeting, job costing, and P&L accountability in a landscape and snow services environment.
• Familiarity with industry systems such as Aspire, LMN, BOSS, Viaesys, Yeti, SitePhotos or other landscape and snow specific business management software.
• Strong leadership skills with a focus on team development, safety culture, and process improvement.
• Working knowledge of fleet, equipment logistics, and seasonal workforce dynamics.
• Strong proficiency in Microsoft Office Suite (Word, Excel, PowerPoint, Outlook) a plus.
• Working knowledge of fleet management software systems.
• Excellent communication, collaboration, and problem-solving abilities.
• Ability to work on the business, not just in it (strategic focus).

Responsibilities

• Develop and implement operational strategies to achieve goals for growth, profitability, and efficiency across all divisions (maintenance, enhancements, snow).
• Partner with sales/account management to ensure contract execution and service delivery align with client expectations across all divisions.
• Support integration of new acquisitions into the operational model and reporting systems.
• Support day-to-day operations to include all facets of landscaping and snow related operations across multiple brick and mortar branches in 6 states as well as a nationally subcontracted division.
• Partner with platform leadership, regional and branch managers to optimize job costing, resource planning, crew deployment, production schedules, equipment use, and resource allocation.
• Learn in-depth and enforce usage of all land/snow operational software across all divisions for both internal and external partners.
• Oversee seasonal labor planning and scheduling to meet production demands.
• Ensure levels of redundancy in operations to account for unpredictable environmental circumstances without compromising service execution or margins.
• Oversee operational forecasting, budgeting, cost control, job costing, and drive key performance indicators (KPIs) such as labor efficiency, revenue per crew, and gross margins.
• Establish benchmarking by geography and service type to drive operational KPIs including, but not limited to, labor hours, route efficiency, revenue per crew, material utilization, and gross margins by job/service type while ensuring productivity levels and cost management stay perpetually aligned.
• Enforce company-wide standards for job quality, safety compliance, and environmental regulations; ensure clean, safe work environments.
• Recruit, train, mentor, and lead district leaders, fostering strong leadership and culture.
• Develop and mentor regional leadership including Directors of Operations/Fleet and General Managers to strengthen knowledge of services and achieving operational excellence.
• Provide operational leadership as needed for operations in transition, acquisitions, and / or gaps in operational coverage.
• Leverage technology to enhance productivity, streamline operations, and implement best practices.
• Identify ways to further optimize operations through alternative equipment management programs, more effective service execution models or other innovative methodologies.

What This Job Offers

• Job Type: Full-time
• Career Level: Executive