Senior Enterprise Project Manager Toronto, ON, Canada

Kensington Tours; Toronto; Hybrid; CAD 120,000 - 135,000; Full time

Job summary

Kensington Tours is seeking a Senior Enterprise Project Manager to own the business case, planning, delivery, adoption, and governance of strategic technology-enabled initiatives. This role connects stakeholders who define the vision with delivery teams responsible for end-to-end execution across technical and non-technical workstreams.

A defining aspect is translating complex data and systems initiatives into structured plans with clear milestones, accountability, and outcomes, bridging

Qualifications

• 7+ years in a project management role delivering strategic enterprise projects.
• Experience with Master Data Management and CRM implementations (Salesforce, Dynamics 365, HubSpot).
• Proven cross-functional, multi-stakeholder project delivery.
• Experience across enterprise initiatives (business, sales, tech, strategy, marketing).
• Structured change management experience and knowledge sharing.
• Bachelor’s degree or equivalent.
• Excellent written and verbal communication with C-suite reporting.
• Exceptional multitasking and planning skills.
• Comfortable operating with ambiguity and creating structure.

Responsibilities

• Shape strategy, define the business case, and articulate value to secure funding.
• Define and manage schedule, scope, and budget across workstreams.
• Serve as liaison between sponsors, stakeholders, and delivery teams.
• Build and maintain detailed project plans and RAID logs.
• Provide regular status updates to leadership.
• Assess team capacity and allocate work across the project lifecycle.
• Design and refine intake, planning, and execution processes.
• Apply change management approaches to drive adoption.

Skills

Senior PM experience

MDM exposure

CRM implementations

Cross-functional leadership

Executive communication

Ambiguity to structure

Education

Bachelor’s degree

Tools

Jira

Confluence

Smartsheet

Job description

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.

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.

ABOUT THE ROLE

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 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

• 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 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 program
• Change management methods and tools
• Budgeting and resource allocation procedures
• 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
• Prior exposure to Master Data Management, enterprise data unification, Customer 360, or CRM implementation (e.g., Salesforce, Dynamics 365, HubSpot)
• 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

• 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. The expected compensation range for this position is: $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. #LI-Hybrid #LI-KC1

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. Final hiring decisions are ultimately made by the hiring team.