Supervisor, Specialized Housing Enforcement

Job Summary

Reporting to the Manager, Specialized Housing Enforcement, the Supervisor, Specialized Housing Enforcement is responsible for overseeing the day-to-day operations of Municipal Law Enforcement Officers (MLEOs) who are tasked with enforcing City by-laws. This includes the enforcement of by-laws related to Rooming and Lodging Houses, Short-term Rentals (STRs), Additional Residential Units (ARUs), Rental Buildings, and associated by-law requirements, among others. The Supervisor supports the delivery of both proactive and reactive enforcement programs. This role provides direct supervision to MLEOs and ensures that investigations are timely, consistent, procedurally fair and legally sound. The Supervisor is responsible for field oversight, mentoring and developing staff, and coordinating with other internal departments and external stakeholders to support comprehensive, tenant-sensitive enforcement approaches. Operating within defined corporate frameworks and procedures, the Supervisor provides operational recommendations to the Manager and supports the implementation of new strategies and policies designed to protect public safety and uphold housing standards.

NOTE: This position may require the successful candidate to work various shifts which include days, evenings, overnight, weekends and statutory holidays and at times, will require overtime. The position may also require use of a uniform and operation of a fleet vehicle. There may be a written test conducted as part of the interview process.

Duties and Responsibilities

• Coordinates daily enforcement operations, ensuring equitable workload distribution and adherence to service level standards
• Adjusts deployment based on seasonal patterns, tenant vulnerability indicators, or high-risk property profiles
• Supports operational continuity and administrative oversight with the Manager, and ensures ongoing service delivery
• Provides technical advice on enforcement related to a variety of by-laws as applied to rental housing, ARUs, STAs, and lodging and rooming houses
• Guides MLEOs in applying complex legal frameworks, including understanding tenant rights, privacy thresholds for entry, and warrant requirements
• Oversees the development and review of Provincial Offences Act (POA) documentation, ensuring evidentiary sufficiency for successful prosecutions
• Provides day-to-day leadership and technical mentorship to MLEOs in the field
• Conducts file debriefings, MLEOs check-ins, and procedural refreshers to ensure enforcement consistency
• Coaches MLEOs on legal thresholds for entry, warrant processes, and balancing enforcement authority with tenant protections
• Supports onboarding and mentoring of new MLEOs, ensuring they are properly trained and resourced
• Maintains a collaborative, respectful team environment rooted in fairness, public accountability, and service excellence
• Acts as a primary escalation point for complex complaints, inquiries, and disputes
• Prepares written correspondence and briefing notes for contentious cases
• Maintains relationships with external organizations to support holistic enforcement strategies
• Represents the City at community meetings or site inspections, explaining enforcement rationale and promoting compliance
• Conducts quality assurance checks on enforcement documentation to ensure timeliness, accuracy, and legal compliance
• Field work and in office requirements. Conducting exterior and interior on site investigations and inspections and may include active construction sites

Skills and Qualifications

• Post-secondary diploma or degree in Law and Security, Regulatory Enforcement, Public Administration, or a related field; or an equivalent combination of education and experience
• Accreditation as a Municipal Law Enforcement Officer, Certified Property Standard Officer through the Ontario Association of Property Standards Officers (O.A.P.S.O), Accreditation in Crime Prevention Through Environmental Design (C.P.T.E.D.). All strongly preferred
• Minimum 5–7 years of municipal enforcement experience, including 2 years in supervisory or lead capacity
• Advanced knowledge of the Municipal Act, Planning Act, Building Code Act, Residential Tenancies Act, Provincial Offences Act, and other enforcement-related legislation
• Experience interpreting and applying complex by-laws related to rental housing, including STRs, ARUs, and lodging and rooming houses
• Demonstrated experience preparing and reviewing both Part I and Part III POA matters, and writing, reviewing, and executing warrants
• Strong understanding of procedural fairness, warrant protocols, and evidentiary requirements related to entry into dwellings
• Excellent written and verbal communication skills, with the ability to resolve conflict and present complex issues tactfully and accurately
• Experience working with vulnerable or at-risk populations in an enforcement or compliance setting is considered a strong asset
• Experience in supporting staff performance and development
• Familiarity with enforcement case management tools and standard business software
• Valid Ontario Class G driver’s licence with a clean abstract and the ability to travel city-wide for site inspections
• A satisfactory Criminal Record Check at the appropriate level is required of the successful candidate, at their own expense, to verify the absence of a criminal record for which a pardon has not been granted.