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Director, CX Optimization & Experimentation

Job in Toronto, Ontario, C6A, Canada
Listing for: Kensington Tours
Full Time position
Listed on 2026-07-07
Job specializations:
  • IT/Tech
    Digital Marketing, Data Analyst
  • Marketing / Advertising / PR
    Digital Marketing
Job Description & How to Apply Below
Toronto, ON, Canada

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 enable 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.

Kensington Tours is seeking a highly analytical and strategic Director, CX Optimization & Experimentation to lead the evolution of our digital acquisition and customer experience across digital properties and traveler touchpoints.

This senior leadership role is for a data-driven optimization expert who combines quantitative rigor with customer-centric thinking. Partnering closely with the Senior Director, Web & Optimization, you will lead end-to-end experimentation strategy across ideation, UX design, execution, analysis, and rollout of winning experiences.

The ideal candidate brings deep experience leading statistically rigorous CRO and experimentation programs within high-traffic digital environments. You are equally comfortable analyzing behavioral data, designing in Figma, interpreting multivariate test results, and partnering cross-functionally to operationalize winning experiences across Marketing, Sales, Product, and Engineering.

This role is both strategic and hands‑on, executing directly while building the experimentation foundation and infrastructure that a future team will scale.

What You’ll Do

Maintain and contribute to the CX optimization and experimentation roadmap across  and all digital acquisition experiences.

Ideate, design, execute, and scale statistically rigorous A/B and multivariate experiments across landing pages, forms, acquisition funnels, itinerary experiences, and lead generation flows.

Translate quantitative and qualitative insights into strategic hypotheses, testing frameworks, and prioritized optimization initiatives.

Create wireframes, UX concepts, prototypes, and test variants in Figma grounded in user behavior, analytics, and conversion best practices.

Lead end-to-end experimentation execution including test planning, quality assurance, launch validation, analysis, significance evaluation, and recommendation development.

Analyze traveler behavior using web analytics, Amplitude, session replay tools, heatmaps, conversion funnels, attribution models, and behavioral segmentation.

Partner closely with Marketing Analytics to apply statistical analysis, probability modeling, funnel analytics, and customer behavior analysis to uncover optimization opportunities and predict conversion outcomes.

Drive optimization initiatives focused on increasing conversion rates, reducing friction, improving lead quality, and maximizing customer lifetime value.

Collaborate cross-functionally with Marketing, Engineering, UX, SEO, Content, and Sales teams to operationalize winning experiences and support organizational change management for implemented variants.

Work closely with Sales and business stakeholders to ensure experimentation outcomes align with operational realities, traveler expectations, and lead quality objectives.

Establish experimentation governance, KPI frameworks, testing methodologies, statistical standards, and reporting practices across the organization.

Present experimentation strategy, analytical findings, and business recommendations to senior leadership and executive stakeholders.

Champion a culture of experimentation, continuous learning, and evidence-based decision-making across the organization.

What You Bring

8–10+ years of experience leading digital experimentation, conversion rate optimization (CRO), behavioral analytics, growth optimization, marketing analytics, or performance-focused UX strategy within complex digital organizations.

At least 5 years leading and owning a growth program or…
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