Director, Loyalty Marketing

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. This is a hybrid position with an expected 3-days a week in office at our Downtown, Toronto headquarters. About the Role  Kensington is launching a new loyalty program for our existing luxury clientele. We're looking for a Director, Loyalty Marketing to own the launch and program end-to-end: internal readiness, lifecycle communications, gifting, and a curated calendar of exclusive client events across North America. This is a highly cross-functional, build-and-launch role for someone who thrives taking strategy to hands-on execution, and who's excited to bring executional excellence to a loyalty program from the ground up — from internal sales training to flagship launch to performance measurement and ROI. Success in this role requires genuine fluency with luxury clientele: understanding their expectations, discretion, and the level of polish required to deliver a best-in-class experience at every touchpoint. What You'll Do Program Setup & Launch Readiness Lead an internal cross-functional (XFN) working group to enable implementation, execution, and sales training of a new loyalty program that will live across our internal tech platforms Develop and lead Phase 1 internal launch readiness, including sales training on all program components Create Phase 1 development of all loyalty program content look and feel and tone of voice partnering with the internal creative team. Build and execute Phase 2 soft-launch execution (late October 2026): triggered lifecycle emails by tier, a welcome gift direct mail, and exclusive product offerings with our internal product and procurement team Analyze in Phase 2 engagement and lead measurement and analytics to optimize and refine program and tactics Launch and execute a flawless integrated Phase 3 full launch planned for early 2027, including a flagship launch event featuring press and influencer attendance Gifting Strategy & Delivery Own the end-to-end gifting program lifecycle across all tiers, including the sales and CRM communications and workflows required to trigger, fulfill, and track each gift on time Partner with Sales to map our gifting & fulfillment process to ensure gifting triggers on tier progression (post-trip) are automated, executed with excell...