Director, Loyalty and Retention Strategy

The Director of Loyalty and Retention Strategy will lead the strategy, evolution, and performance of Caruso Signature - Caruso’s enterprise loyalty ecosystem - while also owning retention and CRM strategy across the portfolio. This role is responsible for setting the long‑term loyalty and lifecycle vision, translating complex data and technology capabilities into clear roadmaps, and rallying cross‑functional teams around initiatives that deepen guest engagement, drive frequency and visitation, and increase lifetime value.

This leader operates at altitude: defining strategy, sequencing priorities, and enabling teams, agencies, and technical partners to execute with excellence. The role balances analytical rigor with guest‑centric creativity, ensuring rewards, communications, and the app experience is differentiated, experiential, and on‑brand.

Loyalty & Retention Strategy

• Own the long‑term strategy and roadmap for the Caruso Signature loyalty program, including rewards, benefits, tiers, experiential offerings, and program innovation
• Define and lead the enterprise retention and CRM strategy, including lifecycle design, audience segmentation, personalization principles, monetization strategy, and communication frameworks across email, push, in-app messaging, and (future) SMS
• Establish clear success metrics and measurement frameworks tied to visitation, frequency, retention, and lifetime value

Program & Platform Leadership

• Serve as the strategic owner of the loyalty and CRM technology ecosystem, including Zeta (Marigold) and Salesforce Marketing Cloud / Data Cloud
• Partner closely with IT as well as engineering and analytics contract support to translate business requirements into scalable technical solutions
• Troubleshoot and optimize loyalty platform capabilities to improve performance and member experience

Data‑Informed Decision Making

• Interpret raw performance data and insights to inform strategy, identify opportunities, and guide prioritization
• Move beyond reporting to synthesize insights into clear recommendations and forward‑looking action plans
• Partner with Integrated Marketing to test and iterate on communications, and identify opportunities to test and iterate on program features

Cross‑Functional & PMO‑Style Leadership

• Lead complex, cross‑functional initiatives requiring alignment across Marketing, IT, Operations, and Brand Partnerships teams
• Apply rigorous program management discipline, including roadmap development, sprint planning, sequencing, and dependency management
• Anticipate risks, surface trade‑offs early, and proactively align stakeholders

Guest Experience & App Evolution

• Define a roadmap for improving the overall loyalty and app experience, ensuring rewards, communications, and features feel cohesive and differentiated
• Partner with Integrated Marketing and Product teams on ASO, acquisition, and engagement strategies that drive app adoption and active usage
• Ensure loyalty communications and experiences balance performance rigor with brand storytelling and experiential value

Partner & Vendor Leadership

• Provide strategic direction and oversight to agency and contract partners, setting clear objectives, success metrics, and accountability frameworks.
• Ensure external partners operate as extensions of the Caruso team, aligned to enterprise priorities and performance goals.

• 5+ years leading loyalty strategy, including program design and lifecycle architecture
• 7+ years of CRM and retention strategy experience, with demonstrated expertise in segmentation strategy, personalization frameworks, and performance optimization
• Hands‑on experience with CRM platforms and loyalty platforms; Experience with Salesforce Marketing Cloud, Data Cloud, and Zeta (Marigold) strongly preferred
• Demonstrated ability to operate at a strategic level while guiding execution through teams and partners
• Experience working closely with engineers and data analysts in agile or sprint‑based environments
• Strong analytical skills with the ability to interpret data, extract insights, and translate findings into strategy
• Proven ability to lead complex, cross‑functional initiatives and build alignment across diverse stakeholders
• Excellent written and verbal communication skills, with the ability to influence and rally teams around complex ideas