Director, Air Operations & Partnerships

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, experts with deep knowledge of their destinations. For over 120 countries worldwide, and across each of our brands – Tours, Cruises, Villas, Yachts, Jets, and Air.

To learn more about Kensington, visit kensingtontours.com.

Job Description

The Director of Air Operations and Partnerships is responsible for supporting Air for Kensington Air and White Label Air, ensuring efficiency, platform optimization, internal adoption, and measurable attachment growth across the business. This role serves as the operational and strategic lead for Kensington Air and White Label Air, supporting a $600M enterprise with the objective to scale beyond $1B. The Director will work across multiple brands, user groups, and branch environments, supporting more than 700 travel professionals.

Close partnership with technology stakeholders — particularly in the ongoing development of our in-house reservation system ADX (>$14M invested) and TMT — is central to success. This position will drive air workflow improvements, performance visibility, and strategic initiatives that expand air usage across all business lines

Essential Job Functions

• Promotion & Internal Engagement

• Act as the internal champion for Kensington Air, increasing awareness and usage across Kensington Tours, Travel Edge Network and Ensemble.

• Build proactive relationships with Destination Experts and sales teams to drive familiarity, confidence, and inclusion of air within itineraries.

• Support air education initiatives, sharing updates, insights, and materials that reinforce air as a value driver across all range companies

• Operational Excellence & Technology Improvement

• Improve efficiency of Kensington Air workflows through enhancements to TMT, ADX, and related booking systems.

• Monitor platform functionality, track developments, and work with stakeholders (R&D, product, operations) to drive improvements.

• Monitor defect trends, participate in automation refinements (auto-ticketing, schedule change tools), and ensure stability of reservation systems.

• Performance Monitoring, Reporting & Insights

• Monitor and report performance of Kensington Air and White Label Air including share, attachment, productivity, error rate, and SLA metrics.

• Build dashboards and reporting structures that provide real-time visibility and support business decision-making.

• Analyze KPIs such as ticket issuance time, commission optimization, and contract performance; identify gaps and recommend corrective action.

• Commercial & Contract Optimization

• Operationalize the use of airline agreements through GDS and internal tools (Contract Management Facility, Commission Optimization Service).

• Ensure contract details, commission structures, and backend incentives are correctly reflected within booking systems.

• Provide support on contract interpretation, upgrade rules, soft-dollar programs, waivers, and complex exchange/ticketing queries.

• Work closely with airline account managers and escalate operational challenges where needed.

• Strategic Growth & Initiative Execution

• Execute initiatives aimed at increasing air attachment and maximizing overall air contribution to the business.

• Partner cross-functionally to design programs that embed air earlier and more consistently in the sales flow.

• Track effectiveness of initiatives, measure outcomes, and refine approaches based on data and feedback

Qualifications

• Extensive experience in a retail travel or air contracting environment.

• Proficiency in at least one GDS: Sabre, Amadeus, Apollo, or Worldspan.

• Strong analytical capability with experience creating dashboards, KPI reporting, and performance insights.

• Proven ability to solve problems using structured reasoning, data interpretation, and judgment where ambiguity exists.

• Skilled communicator with the ability to influence peers, present findings to stakeholders, and simplify technical concepts.

• Demonstrated aptitude for technology adoption and platform improvement work.

• Knowledge of document delivery tools (Trip Case, Virtually There, Cornerstone) and industry consortia tools is an asset.

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.

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