Director of Field Operations

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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