The Director of Delivery Lead Hotel Systems is accountable for end‑to‑end delivery of all applications managed within the Hotel Systems portfolio. This role provides strategic and execution leadership across enterprise hotel technology platforms including PMS, POS, Rapid Response, Spa and Table Management Systems. The role ensures delivery of new and/or upgrade outcomes are tightly aligned to business priorities, hotel operations needs, and enterprise technology standards. Key Responsibilities Strategy & Business Planning Owns the delivery strategy and execution roadmap for the Hotel Systems application portfolio, aligning with enterprise technology strategy and hotel business objectives. Partners with vendors, platform owners and architecture leaders to translate strategic priorities into executable delivery plans with clear outcomes and milestones. Leads prioritization and sequencing of initiatives across the Hotel Systems landscape, balancing new capabilities, regulatory commitments, technical health and operational stability. Provides input into multi‑year planning, capacity forecasting and investment decisions for hotel systems. Identifies opportunities to improve delivery efficiency, simplify platforms and retire technical debt. Supports resource planning and allocation across platform teams to ensure the right capacity and capabilities. Delivery Execution & Performance Accountable for on‑time, on‑budget, on‑quality delivery across all Hotel Systems initiatives. Establishes delivery governance cadence and reporting to provide transparency into progress, risks, dependencies and decision points. Ensures consistent application of agile and hybrid delivery practices across teams while scaling for enterprise complexity. Drives effective program increment planning, sprint execution, release management and production readiness. Proactively identifies and mitigates delivery risks including vendor dependencies, integration complexity and change impacts to hotels. Ensures smooth transition from delivery into operations with clear ownership documentation and support mode. Leads daily stand‑ups and retrospective meetings to help teams implement change effectively. Stakeholder and Partner Management Acts as senior delivery partner to the Global Hospitality Operations Team. Facilitates executive level discussions on delivery trade‑offs, risk mitigation and sequencing options. Builds strong collaborative relationships with regional and hotel stakeholders to ensure solutions meet operational realities. Manages strategic vendor delivery performance, including accountability for outcomes, timelines and quality. People & Culture Creates a culture of accountability, ownership and continuous improvement across delivery teams. Coaches leaders to operate effectively in complex, ambiguous environments. Drives adoption of enterprise agile principles while respecting regulatory and operational constraints of hotel systems. Ensures team capability growth through talent development, succession planning and skills uplift. Governance, Risk & Compliance Ensures delivery adheres to enterprise security, privacy, accessibility and regulatory standards. Partners with security, privacy and enterprise architecture teams to embed compliance and resiliency into delivery from design through release. Oversees budget tracking, vendor spend and financial governance for Hotel Systems delivery initiatives. Requirements Bachelor’s degree in Business or IT discipline (Computer Science). Certifications in Agile / PMI. 10+ years of experience leading large‑scale enterprise technology delivery programs. Proven experience delivering mission‑critical operational systems, preferably within hospitality, travel or multi‑site environments. Strong leadership experience managing senior delivery leaders and complex vendor ecosystems. Deep experience with agile and scaled delivery frameworks including SAFe, Scrum and hybrid models. Strong understanding of hotel systems including PMS, POS, guest‑facing and operational platforms preferred. Excellent communication skills, able to convey complex delivery topics to executive audiences. Experience operating in global environments with diverse stakeholder groups and time zones. Strong program management skills delivering complex software and operational projects. Financial and resource management capability. Experience with release management, DevOps, CI frameworks. Knowledge of front‑end & back‑end development, web, mobile, CRM platforms. Preferred Qualifications & Skills Experience driving end‑to‑end delivery of enterprise platforms through planning, implementation, launch and hand‑off to operations. Proficiency in Agile ceremonies (PI planning, stand‑ups, retrospectives). Strong problem‑solving, risk assessment and root‑cause analysis skills. Exceptional storytelling and stakeholder facilitation skills. Team‑building and cross‑functional leadership experience. Ability to develop buy‑in across partners, functions and management levels. Self‑starter with resilience and ability to operate autonomously. Strategic thinker who anticipates needs and mitigates problems early. Knowledge of Power BI analytics and business transformation methodologies. Excellent time‑management, organization and planning abilities. Capability to prioritize, influence, and manage competing stakeholder expectations. Location & Working Model Based at temporary location 20 York Mills Rd, Toronto Corporate Office. Worked in a hybrid model: 3 days per week on‑site with travel as needed to Four Seasons Corporate Office 1165 Leslie Street, Toronto. Salary Range $125,000 – $165,000. Equal Employment Opportunity Statement 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. #J-18808-Ljbffr