Director, Loyalty Marketing

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 excellence and accurately tracked for each client
• Manage the trigger-based gifting plan and all related CRM communications

Product & Editorial Partnership

• Partner with Product to finalize repeat-exclusive specials and scarcity-driven offerings launched through the repeat-editorial newsletter

Exclusive Event Execution

• Lead execution of an annual repeat-exclusive event calendar (approx. 10 events) spanning multiple formats: intimate, brand-hosted dinners at notable new venue openings; purpose-driven experiences; and curated access to premier partner events and experiences
• Manage each event end-to-end — tailored invitations, custom gifting, content capture, influencer and press coordination
• Deliver against event KPIs: 40% invite acceptance rate, 95% attendance rate, 90+ post-event NPS, and 20% lead conversion rate
• Ensure each event lives on beyond the moment itself with press/influencer capture during the event, content scaling across owned, organic, and paid social after the event, and exit gifting to convert attendees into advocates

What You Bring

• 10+ years of experience in loyalty, lifecycle, CRM, or retention marketing, ideally within travel, hospitality, or a premium consumer brand with an entrepreneurial approach.
• Proven experience leading a CMR and experiential program from concept through execution, including cross-functional stakeholder management
• Experience with CRM/marketing platforms (HubSpot experience preferred; Travel tech experience is a plus)
• Experience managing luxury events end-to-end independently, including vendor and budget management
• Excellent collaboration skills comfortable leading working groups across Sales, Product, Marketing, and Operations
• Flexibility to travel for events across major North American markets including some weekend travel
• Bachelor's degree in marketing or business is ideal

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: $145,000 to $160,000 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-Hyrbid

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.