Director, HOA Governance and Property Management

About Four Seasons:

Four Seasons is powered by our people. We are a collective of individuals who crave to become better, to push ourselves to new heights and to treat each other as we wish to be treated in return. Our team members around the world create amazing experiences for our guests, residents, and partners through a commitment to luxury with genuine heart. We know that the best way to enable our people to deliver these exceptional guest experiences is through a world-class employee experience and company culture.

At Four Seasons, we believe in recognizing a familiar face, welcoming a new one and treating everyone we meet the way we would want to be treated ourselves. Whether you work with us, stay with us, live with us or discover with us, we believe our purpose is to create impressions that will stay with you for a lifetime. It comes from our belief that life is richer when we truly connect to the people and the world around us.

About the location:

Four Seasons Hotels and Resorts is a global, luxury hotel management company. We manage over 130 hotels and resorts and 50 private residences in 47 countries around the world and growing. Central to Four Seasons employee experience and social impact programming is the company’s commitment to supporting cancer research, and the advancement of diversity, inclusion, equality and belonging at Four Seasons corporate offices and properties worldwide. At Four Seasons, we are powered by people and our culture enables everything we do.

Director, HOA Governance and Property Management

The Director, HOA Governance & Property Management is responsible for establishing, implementing, and continuously enhancing governance frameworks, property management standards, and operational best practices across a portfolio of residential properties.

This role provides subject matter expertise in HOA governance, compliance, and property management operations, ensuring alignment between governing documents, operational execution, and homeowner/Board expectations. The Director works across the full residential lifecycle—from development through stabilized operations—to drive consistency, mitigate risk, and elevate homeowner experience and asset performance. This position is highly visible, with employee interactions at various levels, both internally and externally.

What You’ll Be Doing:

HOA Governance & Compliance

• Lead development and standardization of HOA governance frameworks, including Board structures, rules, policies, and operating procedures.
• Review and advise on governing documents, management agreements, and bylaws to ensure operational clarity, enforceability, and alignment with brand standards.
• Establish governance tools (e.g., summaries, playbooks, decision matrices) to support property teams and Boards.
• Provide guidance on Board relations, meeting protocols, elections, and homeowner engagement strategies.
• Oversee compliance with local regulations, licensing requirements, and HOA obligations across jurisdictions.
• Develop governance training programs and resources for property teams.
• Introduce standardized governance and property management tools (e.g., templates, dashboards, reference guides).

Property Management Standards & Operational Excellence

• Define and implement global property management standards across:
  • Asset and HOA management
  • Building operations
  • Risk management and security
  • Capital planning and reserve management
• Develop tools, templates, and frameworks that enhance operational consistency across properties.
• Support Director of Residences and on-site teams in aligning operations with governance requirements and brand expectations.
• Support sensitive or complex Board interactions and conflict resolution.

Development & Pre-Opening Advisory

• Provide insights from portfolio level perspective on governance and property management input during:
  • Deal pursuit and feasibility phases
  • Design & development of operating models and governance structures
  • Advise on HOA set-up, Turnover meeting requirements, and integration of residential operations into mixed-use projects
• Ensure governance and operational considerations are embedded in project documentation early.

Risk Management & Governance Readiness

• Identify governance-related risks (e.g., legal exposure, Board conflicts, compliance gaps) and develop mitigation strategies.
• Ensure availability and accuracy of governance documentation and tools across properties (critical for operational continuity).
• Partner with legal counsel on complex governance matters, including enforcement and policy development.
• Act as a strategic advisor to:
  • Property leadership teams
  • HOA Boards and committees
  • Developers and internal stakeholders

Other

• Drive ongoing improvement initiatives based on audits, site reviews, and portfolio insights.
• Support Residential Team in research, collate and develop collateral, content and tools to communicate best practices in residential and mixed use execution.
• Support and provide consultation to opened and operating projects as required.
• Lead, mentor and develop direct report.
• Participate in Residential Conference.

What You Bring:

• Bachelor’s Degree – Focus on property management / real estate / business.
• Master of Business Administration (MBA) preferred.
• 10 - 15+ years of Residential property management and HOA/community association governance. Preferably multi-property.
• Property manager license such as Certified Property Manager (IREM), Registered Condominium Manager (ACMO) is required.
• Microsoft Excel / Microsoft Word / Microsoft PowerPoint / Microsoft Project / Access.
• Ability to learn and understand additional technical knowledge and skills as required.
• Advance understanding of the branded residential / real estate and vacation home market and industry.
• Great understanding of the hotel market, particularly the luxury segment.
• Excellent knowledge of property management business.
• Excellent knowledge of Governing documents, HOA boards and mixed used project structures.
• Excellent knowledge of property management related operational software and tools.

Key Skills/Who You Are:

• Team player with an excellent attitude and a strong work ethic.
• Humble leadership qualities, able to lead by example.
• Strong interpersonal skills and emotional intelligence.
• High social awareness during difficult discussions and ability to read the room.
• Negotiation and tactical thinking, superior judgment.
• Versatility and balance between conceptual and substantial problem-solving approaches.
• Ability to work in a fast-paced work environment and manage multiple work streams.
• Experience in reducing complex and numerous inputs and qualitative considerations to articulate into a limited set of issues for resolution in a very short timeframe.
• Excellent focus on detail and accuracy.
• Excellent analytical skills a must.
• Strong project management skills.
• High degree of conflict management skills.
• Proven track record of driving results and self-directed high-quality output (written reports, substantive analysis and related insights that drove decision making).
• Balances time and depth adeptly based on risk assessment and context.
• Able to understand business models and legal contracts.
• Has exposure and knowledge of the various functions within an operating company regardless of the industry.

Travel:

• 15-20%

Annual Base Salary Range: $145,000 – $170,000 CAD + additional rewards as part of the total compensation package.

This role will be a Hybrid working model, which will require 3 days per week in the Four Seasons Corporate Office located at 1165 Leslie Street, Toronto, Ontario #LI-Hybrid

Four Seasons is committed to providing employment accommodation in accordance with the Ontario Human Rights Code and the Accessibility for Ontarians with Disabilities Act. If contacted for an employment opportunity, please advise Human Resources if you require accommodation.