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.
The Opportunity
Reporting directly to the CEO, the Chief People Officer is a key member of the Executive Leadership Team, responsible for leading Kensington's global People function and serving as a strategic advisor to the CEO, Board of Directors, and senior leadership team. This is a newly elevated executive mandate for a leader who can build scalable people infrastructure to match a high-growth, globally distributed, entrepreneurial organization.
The CPO will oversee Talent Acquisition, Talent Management, Learning and Leadership Development, Total Rewards, People Operations, Employee Relations, and People Analytics.
This executive will play a central role in building leadership capability, strengthening organizational performance, attracting and developing exceptional talent, and ensuring Kensington's culture and people practices continue to support a growing global business.
Kensington has built a strong people foundation and is now investing in the capabilities, systems, and leadership practices required to support its next stage of growth. This role is four days onsite at Kensington's Toronto Head Office (2 Queen Street East).
Key Responsibilities
People Strategy & HR Leadership
- Serve as a trusted advisor to the CEO, Executive Leadership Team, and Board of Directors on organizational, talent, and leadership matters.
- Develop and execute Kensington's global people strategy in alignment with the company's business objectives and growth plans.
- Translate business priorities into clear workforce, talent, and organizational plans, including organizational design to support Range Group's multi-brand expansion.
- Advise leaders on organizational design, workforce capability, succession, and leadership effectiveness.
- Use people insights and business data to support executive decision-making.
- Build and mentor a high-performing global People team, establishing People as a true strategic partner to the business, and drive a culture of accountability, collaboration, and continuous improvement.
Talent & Organizational Performance
- Build a clear talent strategy that ensures Kensington can attract, develop, and retain the capabilities required for future growth.
- Strengthen performance management, succession planning, and talent review practices across the organization.
- Build leadership development programs that improve management capability and prepare high-potential talent for broader roles.
- Establish clear career paths and development opportunities across critical functions.
- Partner with business leaders to strengthen team effectiveness, organizational health, and workforce performance.
- Develop a strong internal talent pipeline for key leadership and business-critical roles.
Talent Acquisition & Workforce Planning
- Lead a global talent acquisition strategy — spanning executive, professional, campus, high-volume, and field roles — aligned with business priorities and workforce plans across five continents.
- Develop scalable hiring processes and talent pipelines for critical, high-volume, and difficult-to-fill roles.
- Strengthen employer brand and candidate experience, positioning Kensington and Range Group as a destination employer in the luxury travel industry.
- Improve workforce planning, hiring discipline, and recruitment reporting.
- Ensure acquisition and expansion plans are supported by effective talent and workforce strategies.
Learning & Leadership Development
- Develop a learning strategy aligned with Kensington's business priorities and future capability needs, including role-based learning pathways.
- Partner with business leaders to identify capability gaps and create targeted development solutions.
- Ensure training and development reflect Kensington's luxury service standards across a distributed, global workforce.
- Measure the effectiveness of learning programs through business outcomes, leadership capability, and employee growth.
- Foster a culture of continuous learning that supports both individual development and organizational performance.
People Technology, HRIS & People Analytics
- Develop and execute Kensington's People Technology strategy, leading HRIS selection, governance, and roadmap — balancing build-versus-buy decisions, scalability, and return on investment for a growing, multi-entity organization.
- Evaluate and optimize the HR technology ecosystem to deliver a seamless employee and manager experience.
- Develop meaningful people analytics and executive dashboards that support workforce planning, talent decisions, and organizational performance.
- Establish data governance and reporting standards that improve business decision-making.
- Partner with Finance, IT, and business leaders to drive automation, system integration, and self-service capabilities across the employee lifecycle.
Total Rewards, People Operations & Governance
- Provide executive oversight for compensation, benefits, payroll, employee relations, and People Operations.
- Develop competitive, financially responsible reward programs aligned with Kensington's talent strategy and performance expectations.
- Maintain strong governance, compliance, and risk management practices across all jurisdictions.
- Improve People systems, processes, and service delivery to create a consistent, effective employee experience.
- Ensure policies and employment practices are practical, compliant, and aligned with the company's culture.
M&A & Organizational Integration
- Lead the people workstream for acquisitions from due diligence through post-close integration.
- Assess organizational structure, talent, culture, compensation, benefits, and people-related risks during diligence.
- Develop integration plans covering leadership, organization design, workforce, systems, policies, and culture.
- Partner with business and functional leaders to retain critical talent and establish clear accountability following an acquisition.
- Track integration progress and people-related outcomes against acquisition objectives.
Culture, Engagement & Change
- Partner with the CEO and Executive Leadership Team to strengthen and sustain Kensington's culture as the company grows.
- Ensure leadership behaviours, talent practices, and reward programs reinforce the company's values and performance expectations.
- Lead people and organizational aspects of major business changes, including growth, restructuring, and transformation.
- Build clear approaches to employee listening, communication, and engagement.
- Help leaders navigate complex people decisions with consistency, judgment, and care.
- Support the cultural integration of acquired businesses, preserving what makes each organization distinct while building alignment across the group.
Leadership Scope
The CPO will lead an experienced global People team. Direct reports are expected to include leaders across:
- Human Resources Operations
- Talent Acquisition / Recruitment
- Talent Management
- Employee Training & Development
- Total Rewards
- Payroll / Benefits
- Employee Relations
- People Analytics
- HRIS / HR Technology
Qualifications
The ideal candidate is a strategic people leader who combines deep HR expertise with the operational rigor to scale a fast-growing, multi-brand organization.
- Bachelor's degree in Human Resources, Business, Organizational Psychology, or a related discipline; a master's degree and/or CHRL, CHRE, SHRM-SCP, or equivalent designation is considered an asset.
- 15+ years of progressive Human Resources or People leadership experience, including executive-level responsibility, ideally within travel, hospitality, luxury services, or another fast-scaling, globally distributed industry.
- Experience as a Chief People Officer, CHRO, SVP People, or equivalent executive within a large, complex, or multinational organization.
- Demonstrated success developing and executing enterprise People strategies that support business growth and organizational performance, including building HR functions from the ground up or scaling them through high-growth or multi-brand/M&A environments.
- Deep expertise across talent acquisition, talent management, succession planning, leadership development, organizational design, workforce planning, compensation, employee relations, and HRIS/HR technology.
- Experience developing HR technology strategies, people analytics capabilities, and workforce reporting that improve business decision-making.
- Strong understanding of compensation, benefits, payroll governance, employment legislation, and organizational risk management.
- Demonstrated success leading organizational change, business transformation, and large-scale people initiatives.
- Experience supporting mergers and acquisitions, including organizational due diligence and post-acquisition integration.
- Proven ability to build, develop, and lead high-performing People teams.
- Experience operating in a private-equity-backed or founder-led environment is a strong asset.
- Outstanding executive presence, communication, influencing, and relationship-building skills, with experience advising CEOs, Boards of Directors, and Executive Leadership Teams on organizational, talent, and leadership matters.
- Experience operating within a global, high-growth, or entrepreneurial environment is preferred.
Additional Attributes
• Strategic and commercially minded, connecting people decisions to business outcomes while balancing long-term talent strategy with day-to-day execution.
• High integrity, sound judgment, and the courage to provide clear, credible advice.
• Collaborative, low-ego leader who builds strong teams, cross-functional relationships, and trust across all levels of the organization.
• Pragmatic and action-oriented, with a focus on simple and effective solutions.
• Culturally fluent and comfortable operating across a distributed, multi-national workforce.
• Resilient and adaptable, energized by building in a fast-paced, entrepreneurial environment with evolving priorities.
Success in First 12–24 Months
- Developed and implemented a clear global People strategy aligned with Kensington's business objectives and long-term growth plans.
- Strengthened leadership capability through improved succession planning, talent reviews, and leadership development programs.
- Built scalable talent acquisition and workforce planning strategies, strengthening employer brand and improving quality and speed of hiring across all brands and markets.
- Established a People Technology and analytics roadmap — modernizing HRIS, improving data quality, and delivering executive dashboards that support strategic decision-making.
- Established a repeatable people-integration playbook for acquisitions, supporting organizational design, talent retention, and culture integration post-close.
- Built a high-performing, collaborative People team and established People as a trusted strategic partner and advisor to the CEO, Executive Leadership Team, and Board.
Why Kensington & Range Group
This is a rare opportunity to build the people function for one of the fastest-growing names in luxury travel. You will join an ambitious leadership team, work directly alongside the CEO and Board, and play a defining role in building the leadership talent, organizational capabilities, culture, and people infrastructure that will support Kensington Tours, Kensington Travel, Travel Edge, Ensemble Travel, and TripArc through their next stage of growth.This is an opportunity for a people executive who thinks in terms of enterprise value creation, not function management — someone who is energized by building organizations that scale, perform, and win in competitive global markets.
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 actual compensation may vary depending on local market conditions, geography and relevant job-related factors such as knowledge, skills, qualifications, experience, and education/training.
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.