Director of Guest Engagement and ConversionJob SummaryThe Director of Guest Engagement is responsible for shaping and leading a refined, data-informed sales engagement approach on conversion of inbound demand and proactive clienteling (outbound). This role defines how RCYC engages with guests across the sales journey through personalized, timely, and insight-led interactions that elevate conversion, guest recognition, and brand perception.
Sitting at the intersection of Sales, Guest Engagement, Marketing, and Analytics, this leader will define how guest signals, intent, timing, and personalization translate into structured engagement strategies and high-quality clienteling execution. The role combines guest engagement strategy, engagement orchestration, and clienteling execution responsibilities.
Key ResponsibilitiesGuest Engagement and Lifecycle Strategy
- Define and lead the global strategy for guest engagement, activation, and reactivation across all stages of the sales experience
- Establish a clear and elevated vision for how we engage with guests through personalized, relevant, and timely communication
- Develop both short- and long-term strategies that enhance the guest experience while driving conversion, retention, and lifetime value
- Own the sales guest engagement framework, including prioritization logic, engagement sequencing, response timing, and outreach intensity
- Drive improvement of inbound lead conversion through structured, insight-led engagement
- Define engagement approaches across different lead and guest segments, balancing personalization, timing, and commercial opportunity
Guest Timing and Demand Awareness
- Build a sophisticated understanding of guest decision-making cycles and identify the moments that matter most in a guest's journey
- Leverage behavioral insights, engagement patterns, prior voyage history, and time-to-sail indicators to guide outreach timing
- Ensure outreach strategies are not only personalized, but aligned with guest intent and readiness
- Define speed-to-lead expectations and engagement timing rules based on guest intent, value, and behavioral signals
- Establish prioritization rules to focus sales efforts on the highest potential opportunities
Targeting, Personalization, and Guest Activation
- Develop refined segmentation strategies that enable highly tailored guest engagement across key segments
- Lead the design of personalized outreach strategies that elevate guest connection while driving activation and conversion
- Introduce scalable approaches to personalization that ensure each interaction reflects recognition, relevance, and care
Campaign Strategy and Guest Communication
- Oversee the development and execution of multi-channel guest engagement strategies, including outbound calls, email, SMS, and digital touchpoints
- Partner with Sales and Marketing teams to ensure communication is seamless, consistent, and aligned to brand standards
- Ensure all campaigns are curated to enhance the guest experience while supporting commercial objectives
- Ensure engagement strategies are operationalized through clear interaction playbooks, call guidance, voicemail guidance, and outreach standards
- Oversee development of structured storytelling and clienteling approaches aligned with luxury positioning and commercial objectives
Clienteling Execution and Sales Enablement
- Define and continuously refine guest interaction playbooks across different guest segments and engagement scenarios
- Support consistency and quality of execution across the sales organization through guidance, training support, and coaching frameworks
- Partner with Sales leadership to elevate luxury interaction quality, personalization, and conversion effectiveness
Performance Insights and Continuous Enhancement
- Leverage data and insights to understand guest behavior, engagement effectiveness, and conversion outcomes
- Translate insights into meaningful enhancements that elevate both guest experience and business performance
- Establish clear success measures tied to guest engagement, activation, and revenue impact
- Monitor engagement effectiveness across segments, channels, and agents to identify conversion drivers and execution gaps
- Establish feedback loops between Sales, Marketing, and Analytics to continuously improve targeting, messaging, and sequencing
Innovation, Personalization and Automation
- Lead the evolution of personalized guest engagement through advanced tools, automation, and emerging technologies
- Explore opportunities to introduce intelligent, scalable personalization while maintaining a high-touch luxury experience
- Drive a culture of continuous testing and refinement to improve how we connect with guests
Cross-Functional Partnership
- Collaborate closely with Sales, Marketing, Revenue Management, and Analytics teams to ensure alignment across the guest journey
- Ensure a seamless connection between strategy and execution, with clear prioritization and alignment to business goals
- Serve as a strategic partner to leadership in shaping how guest engagement contributes to overall commercial success
- Clarify operational coordination with Marketing around lifecycle triggers, channel sequencing, audience targeting, and guest insights ownership
Leadership and Team Development
- Build an implement an extensive guest engagement strategy
- Foster a culture of excellence, curiosity, and continuous improvement
- Elevate organizational understanding of guest behavior and engagement through clear communication and guidance
CompetencyEducation
- Bachelor's degree in hospitality management, Business Administration, or related field (advanced degree preferred) and/or 10+ years of progressive leadership in luxury hospitality, travel, cruise, or high-end retail environments, with at least 5 years in a director-level role.
Skills & Experience
- 5+ years of experience in guest engagement, sales strategy, CRM, or customer lifecycle management within a service-driven or luxury environment
- Deep experience in Clienteling, including the design and execution of personalized, relationship-driven engagement strategies that leverage guest data, behavioral insights, and past interactions to anticipate needs, elevate the guest experience, and drive incremental revenue
- Demonstrated ability to operationalize Clienteling within CRM platforms (e.g., Salesforce), enabling advisors to deliver highly tailored outreach, curated recommendations, and meaningful follow-ups across the full guest lifecycle
- Strong understanding of guest behavior, decision-making cycles, and demand indicators
- Experience working with sales engagement platforms such as Outreach.IO, Gong, or Sales Loft
- Strong analytical mindset with the ability to interpret data and translate it into actionable strategies
- Proven leadership experience with the ability to influence and align cross-functional teams
- Ability to balance long term strategic vision with near term execution and results
- Strong commercial orientation with demonstrated experience improving conversion through personalized engagement and structured clienteling
- Experience operationalizing engagement models across sales organizations, including prioritization logic, interaction standards, and performance optimization
Work Environment- Full-time, hybrid/typical office environment
- International travel may be required
