Senior Enterprise Project Manager

About Kensington

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 kensingtontours.com.

Role Overview

Position type: Hybrid (2–3 days a week onsite)

Location: 2 Queen St. E, Toronto, ON

The Senior Enterprise Project Manager owns the planning, delivery, 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 workstreams.

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.

What You'll Work On

• End-to-end delivery ownership: Define and manage schedule, scope, and budget across technical and non-technical workstreams, 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.

Knowledge Areas

• Program and project management methodology (Agile, waterfall, hybrid)
• Techniques for planning, monitoring, and controlling complex programs
• 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

Must Have Skills

• 7+ years in a project management role delivering strategic enterprise projects
• Demonstrated experience managing cross-functional, multi-stakeholder projects to completion
• Experience working across enterprise initiatives (business, sales, tech, strategy, marketing, among others)
• Experience with structured change management strategies, documentation, and knowledge sharing
• Bachelor's degree in a relevant field, or equivalent work experience
• Excellent written and verbal communication skills with experience reporting out to the C-suite
• Exceptional multitasking, organizational, and planning skills
• Comfortable operating with ambiguity and building structure from scratch

Nice to Have Skills

• Prior exposure to Master Data Management, enterprise data unification, Customer 360, or CRM implementation (e.g., Salesforce, Dynamics 365, HubSpot)
• Project Management Professional (PMP) or PRINCE2 certification
• Experience with data governance frameworks and cross-functional data stewardship
• Familiarity with tools such as Jira, Confluence, Smartsheet, or equivalent

Compensation

We provide a competitive compensation package with a strong pay-for-performance rewards approach. Employees have the opportunity to participate in incentive programs and compensation tied to business and individual performance.

Expected compensation range: $120,000 to $135,000 CAD

The actual compensation may vary depending on local market conditions, geography, and relevant job-related factors such as knowledge, skills, qualifications, experience, and education/training.

Accessibility and Recruitment

We are committed to providing employment accommodation in accordance with the Ontario Human Rights Code and the Accessibility for Ontarians with Disabilities Act. If you require accommodation due to a disability at any stage of our hiring process, please advise us when completing your application.

The Range Group may use artificial intelligence throughout the recruitment process to screen, assess or select applicants for this position. These tools assist our hiring team but do not replace human judgment. Final hiring decisions are ultimately made by the hiring team.

We thank all candidates for their interest, however, only those selected for an interview will be contacted.