Director of Field Operations

Job Overview

This full-time role is based in Oakville, Ontario, Canada, offering a hybrid work arrangement. While the position allows remote work, candidates must reside in the same local area as the role and be available to attend occasional in-person events or meetings.

About Bridgepoint Maintenance

Bridgepoint Maintenance is an expanding maintenance and field service provider that supports residential and multi-residential properties across Ontario. The company offers a range of services including repairs, inspections, emergency response, turnover services, cleaning, painting, and trade-specific support by leveraging internal teams and approved independent providers. Their network includes a variety of skilled trades including handymen, painters, plumbers, electricians, HVAC and appliance technicians, restorers, laborers, and other specialty service providers.

Role Description

The Director of Field Operations for Ontario will oversee field activities province-wide. This senior leadership position requires hands-on management of maintenance execution, vendor and trade partner supervision, quality assurance, compliance adherence, cost management, and handling of customer escalations. The role involves managing daily operations across multiple service categories such as handyman, painting, cleaning, turnover, and mechanical trades, ensuring proper job assignment, documentation, invoicing, and timely resolution of issues.

The ideal candidate will develop systems, lead and train teams, inspect work in the field, manage escalation processes, and design scalable operating structures for growth across Ontario.

Key Responsibilities

• Oversee daily field operations across various maintenance service lines including cleaning, painting, and mechanical trades.
• Develop and maintain a vendor and trade partner network categorized by city, service type, response time, quality, pricing, and compliance.
• Establish standards for job dispatch, emergency responses, documentation, required inspections, photo documentation, job close-out, and escalation management.
• Implement vendor onboarding processes which include verification of insurance, WSIB clearance, licenses or certifications where required, service agreements, pricing frameworks, banking and tax forms, and safety standards.
• Continuously review and manage work order quality, monitor vendor performance, handle repeat visits, verify quotes and invoices, track SLA adherence, and oversee rework and customer complaints.
• Recruit, train, mentor, and manage performance of field personnel, vendors, supervisors, and emerging leaders within the department.
• Create and maintain standard operating procedures, training programs, inspection checklists, performance dashboards, scorecards, and management guides.
• Address significant escalations involving tenants, owners, vendors, emergency repairs, damage claims, and service failures.
• Collaborate closely with leasing, property management, accounting, customer service, and internal operations to improve operational efficiency and communication.
• Perform property site inspections as required to assess work quality, support training, and resolve on-site operational issues.
• Design and implement a scalable maintenance operation throughout Ontario while upholding quality, compliance, and cost control.

Candidate Profile

Ideal candidates will have a proven record managing field teams, trade vendors, subcontractors, or multi-location service operations, with a clear ability to build, lead, and scale teams.

Essential traits include accountability management of employees and vendors without excessive disruption, deep understanding of residential maintenance challenges and urgencies, willingness to engage directly with field inspections and training, and the ability to manage KPIs alongside operational realities.

Experience Requirements

• Minimum 7 years in field operations, maintenance, facilities, property services, construction, restoration, trade coordination, or vendor management.
• At least 3 years experience managing people, including supervising vendors, team leads, or departments.
• Strong preference for experience specifically in residential service operations.
• Demonstrated skills in workforce development, operational coaching, and team scaling.
• Proficiency with CRM software, work order systems, data dashboards, spreadsheets, mobile field applications, and AI-assisted documentation tools.
• Valid Ontario driver’s license and ability to travel across the province as needed.

Essential Attributes

• Capability to build cohesive teams beyond simply assigning tasks.
• Comfortable enforcing accountability among employees, vendors, and service providers.
• Understanding of the high-pressure, urgent nature of field operations.
• Willingness to personally engage in training, inspections, coaching, and troubleshooting.
• Strong organizational skills necessary to scale operations without compromising quality.
• Adaptability to working in a growing company environment where operational systems are still developing.

Compensation and Benefits

The position offers a base salary between $135,000 and $150,000 per annum, with the possibility of up to $160,000 for candidates with significant Ontario field service scaling experience. A performance bonus ranging from 15% to 25% of base salary is available, contingent on meeting operational KPIs, service quality, cost management, vendor coverage, compliance, and successful team development.

Additional compensation includes possible vehicle allowance or mileage reimbursement, phone allowance, company benefits package, paid vacation time, and business-related travel reimbursements.

Why Work Here

This opportunity enables an experienced leader to shape and grow a maintenance operations platform across Ontario. The successful candidate will directly influence Bridgepoint Maintenance's growth trajectory through leadership in people management, vendor network expansion, service delivery enhancements, and operating system developments.