Director, Office of the CEO (15 Month Contract)

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 120 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, Office of the CEO (15-month Contract)

The Director, Office of the CEO (15-month Contract) plays a pivotal role in ensuring the effectiveness of the CEO Office while driving the execution and oversight of strategic initiatives across the organization. Reporting directly to the SVP, Chief of Staff & Strategic Plan PMO, this role will work closely with senior leadership and cross-functional teams to enhance collaboration, accelerate execution, and support key enterprise priorities.

This position is ideal for a strategic thinker with strong analytical, project management, and communication skills who thrives in a fast-paced, high-impact environment.

Key Activities

Strategic Plan Execution & Governance

• Lead Strategic Plan PMO Activities: Oversee program management for Four Seasons’ Strategic Plan, including KPI and milestone tracking, activity mapping, and cross-functional coordination. Proactively identify risks and opportunities, escalating insights to the Chief of Staff.
• Drive Stakeholder Alignment: Lead efforts to communicate and secure buy-in for the Strategic Plan among internal and external stakeholders, including property ownership. Spearhead initiatives related to the 2026 Property Budget Process, developing materials and delivering training.
• Prepare Executive & Board Updates: Develop high-quality presentations and materials to provide leadership and the Board with clear updates on Strategic Plan progress.
  
  

Owner & Executive Engagement

• Enhance Owner Relationships: Support the execution of initiatives that strengthen engagement with property owners, ensuring alignment between executive leadership and ownership groups.
• Facilitate Executive Engagement: Work closely with internal stakeholders to execute planned improvements in how the CEO and executive team engage with key external partners.
  
  

Office of the CEO Operations

• Support Operating Cadence: Collaborate with Chief of Staff to execute Executive Leadership Team (ELT) operating cadence, including Bi-Weekly Meeting and QBRs, as well as development of Board Materials. Includes content creation as well as coordination with cross-functional teams
• Support Enterprise-Wide Priorities: Contribute to high-priority CEO Office initiatives, including the Annual Leadership Meeting, CEO communications, and other critical organizational projects.
• OCEO Operations: Support ongoing Office of the CEO Operations, including developing briefs for meeting preparation, supporting calendar planning, among others
  
  

What You Bring

• 5+ years of experience in strategy, corporate finance, management consulting, or a related field.
• Experience in hospitality and/or in bringing large transformation programs to life is an asset.
• Proven track record in analytics, project management, and executive communications.
• Bachelor’s degree required; MBA strongly preferred.
• For internal candidates: Minimum 2 years of experience within Four Seasons preferred.
  
  

Who You Are/Key Skills

• Strategic, proactive, and execution-driven: You connect the dots quickly, identify opportunities and risks, and take action.
• Self-starter and passionate learner: You can work independently, assess situations and exercise good judgment. You are excited about learning and taking on complex new challenges.
• Highly collaborative: You thrive in a matrixed environment, quickly build strong relationships, and influence senior stakeholders.
• Strong project management: You excel at managing multiple workstreams, balancing priorities, and meeting tight deadlines.
• Exceptional communication skills: You distill complex information into clear, compelling narratives for executives and external stakeholders (written & verbal).
• Resourceful & adaptable: You operate with a problem-solving mindset, navigating ambiguity with confidence.
  
  

Technical Skills & Knowledge

• Expert in Microsoft Office (PowerPoint, Excel, Word); ability to develop high-impact executive materials.
• Strong data analytics and financial acumen.
• For internal candidate: Familiarity with Four Seasons systems and databases.
  
  

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

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.