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Director, Lifecycle Marketing

Toronto, ON, Canada

Overview 

The Director, Lifecycle Marketing leads Kensington’s customer-journey Centre of Excellence, a dedicated function responsible for driving repeat travel, direct lead growth, and customer lifetime value across all Kensington brands (Tours, Cruise, UltraLuxe, Vacations). 

Reporting to the VP, Marketing & Partnerships, this role owns the end-to-end customer journey from first inquiry through lifelong loyalty. The Director will architect, automate, and optimize personalized communications and experiences turning one-time travelers into lifelong Kensington clients. This is a strategic and operational leadership role requiring a blend of lifecycle strategy, CRM expertise, analytics fluency, segmentation, and cross-functional influence. 


Key Responsibilities 

Loyalty, Retention & Repeat Growth 

  • Lead Kensington’s lifecycle, loyalty, retention, and repeat-traveler strategy across all brands. 
  • Embed repeat traveler growth and direct lead generation as core KPIs across the marketing and commercial organization. 
  • Architect the FY26 Repeat Strategy and 360° Engagement Engine, integrating retention, reactivation, and referral programs into a unified engagement framework. 
  • Design and operationalize full journeys (pre-trip → in-trip → post-trip → reactivation) with personalized touchpoints at each stage. 
  • Partner with Sales, Product, Integrated Marketing, Client Services, and Destination Experts to ensure consistent, high-impact CX across all touchpoints. 
  • Develop segment-specific retention playbooks for first-time, repeat, luxury, UltraLuxe, Cruise, and Vacations clients. 
  • Manage customer reactivation programs and loyalty pilots to improve retention and repeat bookings. 

CRM, Data & Personalization 

  • Oversee CRM strategy and all data-driven communications for both direct customers and travel advisor networks. 
  • Lead and mentor the CRM & Loyalty team in building automated, segmented, behavioral and propensity-based lifecycle journeys. 
  • Support the Manager & Coordinator, Email Marketing in scaling lifecycle campaigns, ensuring flawless execution and segmentation accuracy. 
  • Drive the Contact Strategy Transformation, optimizing frequency, sequencing, channel mix (email, SMS, direct mail), and personalization. 
  • Partner with Data & Analytics and Marketing Operations to strengthen CRM infrastructure (HubSpot), improve data hygiene, and standardize reporting dashboards. 
  • Develop data architectures, audience hierarchies, and segmentation logic across brands. 
  • Introduce frameworks for propensity modeling, lead scoring, predictive signals, and behavioral segmentation. 
  • Maintain governance and data integrity across CRM, ESP, and martech systems. 
  • Use traveler profiles, trip history, and predictive indicators to deliver hyper-personalized storytelling, recommendations, and offers. 

Loyalty, Gifting & High-Touch Experience Programs 

  • Own the strategy, structure, and evolution of Kensington’s Loyalty & Gifting Program, including tiers, benefits, and measurement. 
  • Design high-touch moments (anniversary gifts, surprise-and-delight, Memory Book, Luggage Tag program, Pre-Trip Experience). 
  • Oversee NPS, CSAT, and advocacy journeys; design post-trip experiences that drive rebooking and referrals. 
  • Collaborate with Brand, Product, Partnerships, and Customer Care to deliver exclusive offers, content, and co-branded activations. 
  • Establish loyalty and gifting KPIs, reporting, and optimization loops to track participation, sentiment, and repeat impact. 
  • Partner with external organizations (e.g., Giants of Africa) to align engagement with social impact initiatives. 

Lifecycle Campaigns, Automation & Partner Integration 

  • Lead the development of integrated, multi-channel lifecycle campaigns across email, paid media, SMS, content, and direct mail. 
  • Oversee the Manager and Coordinator, Email Marketing in delivering segmented, automated, and behavior-driven campaigns. 
  • Integrate partner, tourism-board, and co-op opportunities into lifecycle journeys across Tours, Cruise, UltraLuxe, and Vacations. 
  • Architect and optimize automated workflows across pre-trip, on-trip, and post-trip journeys, leveraging AI and personalization. 
  • Manage CRM platform enhancements, ESP integrations, predictive send-time optimization, and dynamic content capabilities. 
  • Maintain a rolling campaign calendar aligned to seasonality, brand priorities, product trends, and partnership activations. 
  • Lead A/B and multivariate testing across lifecycle journeys to maximize engagement and conversion. 

Performance Measurement & Optimization 

  • Define and track core lifecycle KPIs, including: 
  • Repeat Travelers – YoY returning clients 
  • Direct Rebookings – % rebooking through owned digital channels 
  • Retention Rate – within 12–24 months 
  • Lead Volume & RAQs – lifecycle-driven contribution 
  • Loyalty Engagement – tier activity, benefit usage, NPS 
  • Customer Lifetime Value (CLV) 
  • Unsubscribes & Data Health 
  • Build and maintain dashboards and executive scorecards for leadership review. 
  • Present quarterly strategic insights, lifecycle performance, and CX optimization recommendations to executive leadership. 
  • Foster a data-driven, test-and-learn culture across CRM, email, automation, and engagement programs. 

Cross-Functional Leadership & Organizational Impact 

  • Lead, coach, and develop a growing lifecycle organization (CRM, Loyalty, Email). 
  • Serve as a key member of the Marketing leadership team, contributing to strategic planning, forecasting, and CX strategy. 
  • Champion customer-centricity, AI-enabled marketing, personalization, and automation across the organization. 
  • Partner closely with Integrated Marketing, Brand, Partnerships, Sales, and Operations to ensure lifecycle programs drive overall commercial objectives. 
  • Manage key agency, martech, and strategic vendor relationships supporting CRM, automation, personalization, and loyalty. 

Qualifications 

  • Bachelor's degree in Marketing, Communications, Business, or related field (MBA an asset). 
  • 8–10+ years in CRM, lifecycle, retention, or loyalty within luxury travel, hospitality, or premium consumer brands. 
  • Proven track record driving repeat traveler growth, retention, or CLV improvements at scale. 
  • Expertise in CRM/automation platforms (HubSpot preferred). 
  • Strong data literacy and ability to turn insights into segmentation and personalization strategies. 
  • Experience designing loyalty, gifting, or advocacy programs. 
  • Excellent communication, leadership, and cross-functional influencing skills. 
  • Passion for travel, personalization, and exceptional guest experiences. 

Cultural Fit 

  • Customer-obsessed with a deep passion for loyalty and experience design. 
  • Strategic and hands-on, comfortable building new capabilities in a fast-paced, entrepreneurial environment. 
  • Collaborative, curious, and driven to elevate CX across journeys and channels. 
  • Believes loyalty is earned through personalization, empathy, and service—not incentives alone. 
  • Embodies Kensington’s values of excellence, curiosity, connection, and crafting unforgettable journeys. 

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