Director of Field Operations

Overview

Job

• Full-Time
• Oakville, Ontario, Canada
• Hybrid

Important Location Requirement

This is a remote position; however, candidates must be located in the same country, city, or region where the job is posted. The successful candidate must be available to attend a local office, meeting, training session, or company event if requested.

Please only apply if you are based in the location listed on this job posting. Remote does not mean the position is open worldwide.

About Bridgepoint Maintenance

Bridgepoint Maintenance is a growing maintenance and field service company supporting residential and multi-residential properties across Ontario. We provide repairs, inspections, emergency response, turnover services, cleaning, painting, and trade support through internal teams and approved independent service providers.

Our network includes handymen, painters, cleaners, plumbers, electricians, HVAC technicians, appliance technicians, labourers, restoration vendors, and other specialty trades.

We are looking for a senior operations leader who can build, manage, and scale a serious maintenance operation across Ontario.

About The Role

Bridgepoint Maintenance is hiring a Director of Field Operations – Ontario to lead our province-wide field operations.

This is a senior, hands-on leadership role for someone who understands maintenance execution, residential service urgency, vendor and trade management, quality control, compliance, cost discipline, and customer escalations.

You will oversee day-to-day operations across handyman, painting, cleaning, turnover, and mechanical trade services. This includes ensuring jobs are assigned, completed, documented, invoiced, and escalated with accuracy, urgency, and accountability.

This is not a desk-only role. We need someone who can build systems, lead teams, inspect work, train staff, manage vendors, resolve escalations, and create an operating structure that can scale city by city across Ontario.

The right candidate will not only manage today’s workload, but also build the department structure needed for long-term growth.

Interview Process

Qualified candidates will receive a link to complete a pre-recorded interview via email 24-48 hours after applying.

Once the pre-recorded interview has been completed, our recruiting team will review the submission. Candidates who appear to be a strong potential fit will be invited to complete a second interview, which will be conducted live.

The Director Of Field Operations Will Be Responsible For

• Leading daily field operations across maintenance, cleaning, turnover, painting, and mechanical trade services
• Building and managing vendor and trade coverage by city, service category, response time, quality, pricing and compliance status
• Setting standards for dispatch, emergency response, job documentation, photo requirements, inspections, close-outs, and escalations
• Creating and enforcing vendor onboarding requirements, including insurance, WSIB clearance where applicable, licences or certifications for regulated trades, service agreements, pricing schedules, banking details, tax forms, and safety expectations
• Reviewing work order quality, vendor performance, repeat visits, quote accuracy, invoice issues, SLA breaches, rework, and customer complaints
• Hiring, training, coaching, and performance-managing field staff, vendors, supervisors, and future department leaders
• Developing SOPs, training materials, inspection checklists, KPI dashboards, scorecards, and manager playbooks
• Handling serious escalations involving tenants, owners, vendors, technicians, emergency repairs, damage disputes, service failures, or safety concerns
• Partnering with leasing, property management, accounting, customer service, and internal operations teams to improve speed, communication, and accountability
• Visiting properties when required to inspect work, assess field issues, support training, and resolve operational breakdowns
• Building a scalable Ontario-wide maintenance operation while maintaining service quality, compliance, and cost control

The Person We Need

We are looking for someone who has successfully managed field teams, trade partners, subcontractors, vendors, or multi-location service operations.

The Ideal Candidate

• Knows how to build teams through hiring, onboarding, coaching, performance management, progressive discipline, and leadership development
• Can hold employees, vendors, and trades accountable without creating unnecessary chaos or turnover
• Understands residential maintenance, turnover readiness, customer pressure, service urgency, and real field conditions
• Is comfortable inspecting work, auditing photos, visiting properties, training teams, and stepping in when issues need leadership
• Can scale operations across Ontario while keeping quality, compliance, pricing, and response times under control
• Uses KPIs, dashboards, and scorecards to manage performance, but does not rely on reporting alone when field action is needed
• Can manage difficult escalations calmly and fix the root cause afterward

Required Experience

• 7+ years of experience in field operations, maintenance operations, facilities, construction service, property maintenance, restoration, home services, trade coordination, or vendor management
• 3+ years of experience managing people, vendors, supervisors, team leads, or department leaders
• Experience with residential service operations is strongly preferred
• Proven ability to hire, train, coach, performance-manage, and build scalable teams
• Strong understanding of field service execution, quality control, vendor performance, customer escalations, and cost control
• Experience using CRM systems, work order platforms, dashboards, spreadsheets, mobile field tools, and AI-assisted documentation
• Valid driver’s licence and ability to travel within Ontario as required

To Be Successful In This Role, You Must

• Be able to build a team, not just manage tasks
• Be comfortable holding employees, vendors, and service providers accountable
• Understand the urgency and pressure of field operations
• Be willing to train, inspect, coach, and solve operational problems directly
• Be organized enough to scale across Ontario without service quality falling apart
• Be comfortable working in a growing company where systems must be built, improved, enforced, and refined

Compensation

The target base salary for this role is $135,000–$150,000 per year, based on experience.

Exceptional candidates with direct, proven Ontario field service scale experience may be considered up to $160,000 base salary.

This role also includes eligibility for a performance bonus of 15%–25% of base salary, tied to operational KPIs, service quality, cost control, vendor coverage, compliance, and successful team build-out.

Additional compensation and support may include car allowance or mileage reimbursement, phone allowance, standard company benefits, paid vacation, and business travel reimbursement.

Why Join Bridgepoint Maintenance

This is an opportunity to build and lead a maintenance operations platform across Ontario. You will be responsible for shaping the people, systems, vendor network, service standards, and operating discipline required to scale the company properly.

The right person will have the opportunity to create structure, hire leaders, improve service delivery, and directly impact the long-term growth of Bridgepoint Maintenance.

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