Director, Loyalty Marketing

Kensington • Toronto, ON

17h • CA$145,000 - CA$160,000 • Hybrid

About The Position

Kensington is launching a new loyalty program for its existing luxury clientele. This role will own the program from end-to-end, including 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 is excited to bring executional excellence to a loyalty program from the ground up. Success 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.

Requirements

• 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.
• Bachelor's degree in marketing or business is ideal.

Nice To Haves

• Travel tech experience is a plus.

Responsibilities

• Lead an internal cross-functional (XFN) working group to enable implementation, execution, and sales training of a new loyalty program.
• 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.
• 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.
• 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.
• Partner with Product to finalize repeat-exclusive specials and scarcity-driven offerings launched through the repeat-editorial newsletter.
• 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.

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.

What This Job Offers

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