Director, Hospitality Technology Delivery

This leader is single minded in driving predictable high quality delivery while modernizing delivery practices strengthening cross functional collaboration and ensuring operational readiness across a global hotel environment.

The role partners closely with Platform Owners, Architecture & Security Operations and external vendors to deliver scalable secure and resilient hotel systems.

This role is based in our temporary location of 20 York Mills Rd, then the Four Seasons Hotels and Resorts, Toronto Corporate Office, reporting to the Senior Director, Hotel Systems. This role involves interactions with both internal and external stakeholders at various levels.

What You’ll Be Doing:

Strategy & Business Planning

• Owns the delivery strategy and execution roadmap for the Hotel Systems application portfolio in alignment 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 dependencies 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 the platform teams to ensure the team has the right capacity & 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 a senior delivery partner to Global Hospitality Operations Team.
• Facilitates executive level discussions on delivery tradeoffs 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, testing through release.
• Oversees budget tracking, vendor spend and financial governance for Hotel Systems delivery initiatives.

What You Bring:

• 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.
• Demonstrated ability to communicate complex delivery topics clearly to executive and operational audiences.
• Experience operating in global environments with diverse stakeholder groups and time zones.
• Strong program management skills in delivering complex software, and operational projects .
• Enterprise delivery leadership and execution excellence.
• Strong understanding of hotel systems integration to front-end, back-end, and middlware software development on web, mobile app, CRM and other platforms.
• Strong understanding of release management, working closely with Dev Ops and implementing CI frameworks.
• Strong financial and resource management capability.

Who You Are:

• Delivery Success: Proven track record of taking new and/or upgrade of enterprise platforms through planning, implementation, launch & hand off to operations. Experienced in leading Agile ceremonies (PI planning, stand ups, retrospectives, …) and ensures all stakeholders are updated in a timely matter.
• Problem Solver: An ability to quickly break down ambiguous problems no matter the context. The skill to identify risks/root causes at pace, and synthesize an approach to problem investigation and resolution.
• Communication & Storytelling: Skilled in the ability to communicate complex challenges, risks & options analysis in a clear and concise presentation. Confident in guiding stakeholder discussions & facilicating workshops with clear next steps / ownership.
• Team Builder: A proven ability to lead and develop others in a cross functional environment (Product owners, IT platform leads, IT security, 3rd party vendors, …).
• Create Buy-In: Develops strong relationships across all partners, functions and management levels, generating continuous collaboration, iteration, input, and buy-in from others.
• Proactive Self-Starter: Delivers results while managing multiple priorities with lean resources in a dynamic and ever-changing environment; resilient and can operate autonomously.
• Exceptional communicator with ability to communicate complex ideas, navigate stakeholders, make decisions, and generate buy in across people at all levels of the organization.
• Critical thinker with ability to anticipate needs and problems and avert them before they happen.
• Possesses maturity, humility, and situational sensitivity; able to handle conflict constructively.
• Works effectively in situations where information is ambiguous and easily switches approaches as required.
• Exhibits organizational and political intelligence.
• Ability to handle multiple competing priorities and wear many hats.
• Ability to look beyond immediate problem and assess longer term implications.
• Ability to work with different personality types to bring together ideas and formulate solutions.
• Ability to structure and solve ambiguous problems.
• Strong leadership skills and successful business leader focused on creating trust and psychological safety.
• Track record of attracting, developing and motivating a highly capable team.
• Highly developed interpersonal skills with ability to effectively engage with leaders and team members across the organization.
• Possesses a continuous improvement mindset and takes personal responsibility and ownership.
• Proven program, project and product management experience (Agile SAFe, SCRUM, PMP, …) utilizing agile methodologies & tools (Jira, Confluence, …).
• Knowledge of Front-end & Back-end development across Web, Mobile app & PMS, POS technologies.
• Knowledge in utilizing Analytics capabilities (Power BI).
• Knowledge of business transformation metholodgy & practices (business processes, value stream mapping, …).
• Excellent time management, organization, and planning skills are essential.
• Able to set priorities, influence others, and manage various stakeholder expectations.
• Ability to translate business requirements into technical solutions.
• Demonstrated success in relationship management.
• Self-starter with a demonstrated ability to work collaboratively to achieve results as part of a cross-functional team.
• Able to effectively prioritize and multi-task under tight deadlines.
• Strong verbal, written, presentation and interpersonal skills are required.
• Understanding of travel and hospitality industry an asset.

Salary Range: $125,000 - $165,000  

This role will be a Hybrid working model, which will require 3 days per week at our temporary 20 York Mills Road, Toronto, Ontario location with travel, as needed, to our 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.