Group CFO

Kensington • Toronto, ON

8d • Onsite

About The Position

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.

The Opportunity
Reporting directly to the CEO, the Chief Financial Officer (CFO) is a key member of the Executive Leadership Team, responsible for leading Kensington's global Finance organization across Kensington Tours, Kensington Travel, Travel Edge, Ensemble Travel, and TripArc, and serving as a strategic partner to the CEO and Board of Directors. The CFO will oversee Corporate Development & M&A, Financial Operations, Treasury, and FP&A, with a particular focus on capital strategy, debt financing, dealmaking, and long-term enterprise planning.

A flagship priority for this role is leading a $5–10 billion roll-up strategy across North American leisure travel agencies and tour operators — sourcing, negotiating, and closing acquisitions that will define Kensington's next stage of growth. Kensington has built a strong financial foundation and is now investing in the capabilities required to support its next stage of growth. This role is based at Kensington's Toronto Head Office, with an expectation of being in-office four to five days per week.

Requirements

• Bachelor's degree from a leading university with a strong academic record; MBA, CPA, and/or CFA preferred.
• Career foundation in investment banking and/or private equity at a top-tier firm, with substantial transaction experience — strongly preferred.
• Subsequent operating experience gained inside a portfolio or high-growth company, with direct accountability for P&L, teams, and business results. Candidates who pair transaction pedigree with hands-on operating leadership will stand out.
• 15+ years of progressive finance leadership experience.
• Experience as a Chief Financial Officer or equivalent senior finance executive within a large, multinational organization of 1,000+ employees.
• Demonstrated experience leading acquisitions from evaluation and due diligence through execution and integration, ideally including roll-up or consolidation strategies.
• Deep expertise in valuation, financial modelling, corporate finance, and capital allocation.
• Proven experience in Treasury, debt financing, and banking relationships.
• Experience preparing board-level financial reporting and materials for internal boards and external stakeholders such as banks, suppliers, and clients.
• Strong people leadership, executive communication, and influencing skills, with a reputation as a manager of people who operates effectively in the real world.
• Experience in a global, high-growth, or entrepreneurial organization is preferred.
• The ideal candidate is a strategic finance executive who combines the analytical rigor of an investment banking background with the credibility of having operated a real business. We are prioritizing candidates whose careers began in investment banking or private equity and who have since moved into hands-on operating leadership.
• Strategic and commercially minded, with the ability to balance long-term direction and operational execution.
• Entrepreneurial and deal-driven, energized by sourcing, negotiating, and closing complex transactions.
• High integrity, sound judgment, and professional credibility.
• Collaborative, low-ego leader who builds strong teams and cross-functional relationships.
• Resilient and comfortable operating in a fast-paced environment with evolving priorities.
• Reflects Kensington's culture and work ethic, with the team management skills and track record of delivering results expected of future enterprise leadership.

Nice To Haves

• MBA, CPA, and/or CFA preferred.
• Career foundation in investment banking and/or private equity at a top-tier firm, with substantial transaction experience — strongly preferred.
• Subsequent operating experience gained inside a portfolio or high-growth company, with direct accountability for P&L, teams, and business results. Candidates who pair transaction pedigree with hands-on operating leadership will stand out.
• Experience in a global, high-growth, or entrepreneurial organization is preferred.
• The ideal candidate is a strategic finance executive who combines the analytical rigor of an investment banking background with the credibility of having operated a real business. We are prioritizing candidates whose careers began in investment banking or private equity and who have since moved into hands-on operating leadership.

Responsibilities

• Serve as a trusted advisor to the CEO, Executive Leadership Team, and Board of Directors.
• Help shape Kensington's long-term strategy through financial analysis, commercial insight, and capital allocation.
• Develop and execute the company's global financial strategy.
• Evaluate strategic investments, new business opportunities, and growth initiatives.
• Lead the global Finance organization and build a culture of accountability, collaboration, and continuous improvement.
• Develop and mentor a high-performing finance leadership team.
• Build and maintain a complete North America database of travel agencies and tour operators to inform sourcing and prioritization.
• Identify and prioritize M&A targets, with special attention to luxury leisure travel.
• Lead direct discussions with potential sellers to originate and advance deals.
• Build a comprehensive deal pack for every target, incorporating projected synergies and post-merger integration costs into overall deal value.
• Work with the internal legal team to close deals and track agency integration.
• Coordinate external advisors, including investment banks, legal counsel, and diligence providers, as needed.
• Prepare investment recommendations and business cases for executive leadership and the Board.
• Lead integration planning from due diligence through post-close execution, including financial reporting, systems, governance, and operating models.
• Track acquisition performance, integration progress, and achievement of expected returns against the roll-up target.
• Provide executive oversight for Accounting, Financial Reporting, Tax, and Financial Operations across the organization, led through the SVP, Finance.
• Ensure accurate, timely, and transparent financial reporting.
• Maintain strong financial controls, governance, and risk management practices.
• Oversee the year-end audit process and all statutory and regulatory reporting obligations.
• Continue improving financial systems, processes, and operational efficiency.
• Support the finance leadership team in scaling accounting and reporting capability as the portfolio grows through acquisition.
• Build and lead a strong Treasury function supporting Kensington's global operations and growth plans.
• Develop and execute capital structure strategies that maximize financial flexibility and support future acquisitions.
• Lead banking relationships and negotiate debt facilities and acquisition financing.
• Manage liquidity, working capital, foreign exchange exposure, and financial risk.
• Oversee insurance programs and related risk management practices.
• Improve treasury processes, governance, and reporting.
• Own the weekly, monthly, and full-year planning and reporting cycles, continuing to strengthen Kensington's internal management reporting.
• Build and lead board-level financial reporting for the internal Board of Directors, translating company performance into clear, decision-ready narratives.
• Extend board-caliber reporting to key external stakeholders — including suppliers, banks, and clients — ensuring consistent, credible financial communication across all audiences.
• Lead enterprise-wide budgeting and forecasting activities in support of the company's growth plans.
• Improve management reporting, financial models, and executive dashboards to support business decisions.
• Develop and monitor KPIs and performance tracking systems that give the CEO and business leaders real-time, decision-ready financial insight.
• Built a complete North America database of travel agency and tour operator targets, with a prioritized luxury-leisure M&A pipeline.
• Advanced multiple priority acquisition conversations toward signed letters of intent, with deal packs reflecting synergy and integration costs.
• Closed and begun integrating Kensington's first roll-up acquisitions under a disciplined, repeatable M&A process.
• Strengthened Kensington's Treasury function, capital structure, and financing strategy.
• Launched board-level financial reporting extended to the internal Board, banks, suppliers, and key clients.
• Built strong relationships with the existing Finance leadership team and become a trusted advisor to the CEO and Board.

Benefits

• Competitive compensation package with a strong pay for performance rewards approach.
• Opportunity to participate in incentive programs and compensation tied to business and individual performance.
• Employment accommodation in accordance with the Ontario Human Rights Code and the Accessibility for Ontarians with Disabilities Act.

What This Job Offers

• Job Type: Full-time
• Career Level: Executive