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Director of Field Operations

10 hours ago

Mississauga, Ontario, Canada Lifestyle Home Products Full time

Director of Field Operations & In-Field Marketing

About WIN

WIN (Warehouse Installation Network) is the dedicated national lead generation partner for Lifestyle Home Products, the largest independent manufacturer of sunrooms, windows, doors, the all-Canadian True North Bath Remodel, Lennox, and others.

Through partnerships with major retailers across the Country, WIN designs and executes in-store and event-based programs that connect directly with homeowners and generate high-quality, leads for our home improvement clients. As we continue to scale, we are investing in the next level of operational and commercial leadership.

Position Overview

WIN is seeking a Director of Field Operations & Marketing to provide strategic and operational leadership across its field programs.

Reporting directly to the CEO, this role is responsible for:

  • Overseeing the performance of Team Leads, Squad Leaders, and field representatives
  • Designing and refining the systems and processes that support field execution
  • Leading the development and rollout of new acquisition channels, including canvassing and events

This position is ideal for an experienced, entrepreneurial sales-oriented operator who is comfortable owning both day-to-day execution and the design of scalable, repeatable systems.

Key Responsibilities

Field Leadership & Performance Management

  • Lead and support a multi-layered team structure (10 Team Leads, 8+ admin and support staff, and 100+ field representatives) across multiple regions
  • Establish clear performance expectations, KPIs, and routines for Team Leads and their teams
  • Conduct regular performance reviews and operational meetings focused on lead volume, lead quality, staffing, and compliance with standards

Operational Systems & Process Design

  • Develop and optimize systems for scheduling, coverage, store allocation, and shift management
  • Build and refine onboarding, training, and performance management workflows to ensure consistency and quality across all markets
  • Implement and maintain practical scorecards and reporting tools (primarily in Google Sheets/Excel and CRM platforms) to support data-driven decision-making

New Channel Development (Canvassing & Events)

  • Build and launch of canvassing program (door-to-door), including territory planning, staffing models, performance metrics, and reporting
  • Build and launch an events program (home shows, fairs, markets), including event selection, logistics planning, deployment, and post-event analysis
  • Create structured playbooks and SOPs so new channels can be scaled efficiently and managed by the leadership layer

Operational Problem Solving & Continuous Improvement

  • Monitor field performance and proactively identify operational risks, trends, and improvement opportunities
  • Address issues such as coverage gaps, store concerns, logistics challenges, and variance in performance in a timely, structured manner
  • Ensure accurate, timely reporting and provide clear weekly and monthly operational updates and recommendations to the CEO and leadership team

Qualifications

Experience

  • Minimum 3-5 years of progressive experience in field operations, sales operations, retail or regional management, home services, door-to-door, events, or a closely related environment
  • Demonstrated experience managing front-line teams through a leadership layer (team leads, supervisors, regional managers)
  • Proven track record of designing or significantly improving operational systems, processes, and performance frameworks
  • Bilingual is an asset

Skills & Competencies

  • Strong operational and commercial mindset, with a focus on measurable results (lead volume, quality, efficiency)
  • High degree of initiative and ownership; able to move work forward with limited direction
  • Excellent organizational skills and attention to detail, with the ability to manage multiple markets and priorities concurrently
  • Proficiency with Google Sheets/Excel and familiarity with CRM/field tools (e.g., Salesforce, i360, SureCommand or similar)
  • Clear, professional communication skills with the ability to work effectively with both leadership and front-line staff

Other Requirements

  • Valid driver's license and reliable vehicle; regular and weekly visits to stores and events will be required.

Why Join WIN?

  • Strategic impact: Direct influence over how a national field operation is structured, managed, and grown
  • Building opportunity: Opportunity to design and institutionalize scalable systems and channels in a high-growth environment
  • Leadership exposure: Direct reporting line to the CEO and involvement in key operational and growth decisions
  • Growth potential: As WIN expands, this role has clear potential to grow in scope and seniority.

Compensation & Schedule

  • Starting salary: $70,000–$105,000 CAD per year, commensurate with experience
  • Performance-based bonus linked to lead generation results and overall company performance
  • Mileage reimbursement for approved travel to stores and events

How to Apply

Qualified candidates are invited to submit their resume and cover letter to:

While we thank all those with an interest in this role, only the candidates selected for an interview will be contacted.

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