Vice President of Operations

VP OF OPERATIONS FOR LANDSCAPE & SNOW
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.

Key Responsibilities:

• Strategic Leadership :
  • 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.
• Operational Oversight :
  • 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.
• Financial Management :
  • 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.
• Quality & Safety :
  • Enforce company-wide standards for job quality, safety compliance, and environmental regulations; ensure clean, safe work environments.
• Team & Talent Development :
  • 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.
• Technology & Process Improvement :
  • 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.

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).

Winter Services LLC 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.