Director, Hospitality Technology Delivery Job at Four Seasons (Toronto)

Job Description

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 that delivery of new and/or upgrade outcomes are tightly aligned to business priorities hotel operations needs and enterprise technology standards. 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.

Job Responsibility

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
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
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
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
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

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
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
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

Nice to have

Understanding of travel and hospitality industry an asset
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, …)
Strong understanding of hotel systems including PMS, POS, guest facing and operational platforms preferred

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Director, Hospitality Technology Delivery

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