Senior Enterprise Project Manager

Kensington delivers the world’s most personal travel experiences. We bring to life each client’s desire to travel in a way that’s tailored specifically for them, in the company of local private guides who ensure that they enjoy the authentic best of their destination. The result is a unique journey rich in memories that last a lifetime!

We achieve this because of our extraordinary people, passionate experts with deep knowledge of their destinations. They are what enables us to deliver remarkable experiences in over 120 countries worldwide, and across each of our businesses – Private Touring, Cruises, Villas, Yachts, Expeditions, Ultraluxe Land, Private Jets, and Air.

To learn more about Kensington, visit

This is a hybrid position with currently 2-3 days a week onsite from our office located at 2 Queen St. E in Toronto, ON.

The Senior Enterprise Project Manager owns the business casing, planning, delivery, adoption, and governance of strategic projects that sit at the intersection of technology and business. This role is the connective tissue between stakeholders who define the vision and the teams who build and deliver, responsible for end-to-end execution across technical and non-technical work streams.

A defining characteristic of this role is the ability to bridge technology and business: translating complex data and systems initiatives into structured delivery plans with clear accountability, timelines, and outcomes.

• Strategy and business casing:
  Partner with initiative stakeholders to shape strategy, define the business case, and articulate the value and investment rationale needed to secure executive sponsorship and funding approval.
• End-to-end delivery ownership:
  Define and manage schedule, scope, and budget across technical and non-technical work streams, from initiation through go-live and hypercare.
• Stakeholder liaison:
  Serve as the primary point of contact between project sponsors, business stakeholders, and delivery teams, balancing competing priorities with clarity and transparency.
• Project Planning:
  Build and maintain detailed project plans, RAID logs, resource plans, and dependency maps; surface risks proactively before they become blockers.
• Progress tracking and reporting:
  Monitor milestones and performance metrics; provide regular status updates to leadership, including executive-level reporting.
• Resource management:
  Assess team capacity, allocate work according to skills and experience, and adjust as constraints shift throughout the project lifecycle.
• Process optimization:
  Design and continuously refine project intake, planning, and execution processes to reduce backlog and improve delivery velocity across the organization.
• Change management:
  Apply structured change management approaches to drive adoption of new systems, processes, and ways of working with business teams.
• Task assignment:
  Assign individual workstream tasks to the right contributors based on expertise; reassess and realign as project conditions evolve.

• Program and project management methodology (Agile, waterfall, hybrid)
• Techniques for planning, monitoring, and controlling complex program
• Change management methods and tools
• Budgeting and resource allocation procedures
• Enterprise data concepts: master data management, data unification, data governance, Customer 360, CRM platforms
• Business and technology relationship: understanding how systems decisions drive commercial outcomes
• Implementation planning for multi-user, multi-team environments

• 7+ years in a project management role delivering strategic enterprise projects
• Prior exposure to Master Data Management, enterprise data unification, Customer 360, or CRM implementation (e.g., Salesforce, Dynamics 365,…