Head of Digital Strategy & eCommerce

The Gig: Virgin Voyages is redefining the future of travel—bold, effortless, and unmistakably Virgin. The Director, Digital Strategy & eCommerce is first and foremost a commercial channel owner. This individual is accountable for the revenue performance of Virgin Voyages’ digital ecosystem—VirginVoyages.com, FirstMates.com, and the Sailor App—and owns the strategy that drives Sailors and First Mates to discover, consider, and book. This is not a technology roadmap role. This is a growth and revenue leadership role that happens to operate through digital channels. The right person for this role thinks like a brand strategist and a performance marketer simultaneously. They can craft a creative acquisition strategy that fills the top of the funnel, architect a conversion experience that turns browsers into bookers, and build a seamless digital journey that connects the pre-sail web experience with the Sailor App and digital touchpoints onboard—so the Virgin Voyages experience feels cohesive, intentional, and unmistakably Virgin from the first site visit to the last day at sea. This role requires a rare combination: someone who is commercially obsessed, creatively ambitious, and analytically rigorous. You define what success looks like across every digital touchpoint, hold the channel accountable to revenue targets, and lead a team of senior managers and cross-functional partners to make it happen. You bring the strategy. You own the results. This gig is based at VVHQ - our swanky Virgin Voyages Head Office in Plantation, FL where we follow a hybrid work environment. We can't wait to 'sea' you in person during our Collaboration Days, Tuesdays, Wednesdays, and Thursdays, while you enjoy Mondays and Fridays' as remote days. What You'll Be Up To: Channel Ownership & Commercial Accountability Own the digital channel as a revenue-generating business—accountable for the commercial performance of VirginVoyages.com, FirstMates.com, and the Sailor App, with direct responsibility for driving booking revenue, conversion rates, and digital customer acquisition. Define and own the digital channel strategy end to end: from the creative and media approaches that bring Sailors and First Mates to the site, through the onsite experience that converts them, and into the post-booking journey that deepens engagement and drives ancillary revenue. Set and hold the channel to clear revenue and performance targets—working closely with Finance and Revenue Management to forecast digital contribution, model ROI on investments, and report performance against commercial goals in executive forums. Treat the digital channel with the same rigor and ownership mindset as a P&L: identify gaps, build investment cases, prioritize ruthlessly, and drive results with urgency and accountability. Acquisition Strategy & Creative Demand Generation Develop and own a creative, insight-led strategy to drive qualified Sailor and First Mate traffic to Virgin Voyages’ digital properties—going beyond paid media to think holistically about organic, content, SEO, CRM-driven re-engagement, and partner-driven acquisition. Partner with Brand, Paid Media, CRM, PR, and Content teams to ensure the acquisition strategy is cohesive—so every channel and touchpoint is working together to bring the right audiences to the right digital experience at the right moment. Identify untapped acquisition opportunities and audience segments; build and present business cases that unlock new sources of demand for the digital channel. Champion creative ambition in the digital experience—pushing the team and partners to build digital moments that are not just functional but genuinely on-brand, surprising, and worth sharing. Conversion Optimization & Booking Experience Own the end-to-end booking funnel across VirginVoyages.com and FirstMates.com—with obsessive focus on removing friction, improving conversion at every step, and making it as easy and exciting as possible to book a Virgin Voyages sailing. Lead a rigorous A/B and multivariate testing program across the booking funnel—ensuring the team is continuously experimenting, learning, and improving conversion performance based on evidence, not intuition. Partner with the Data Insights & Intelligence team to diagnose funnel performance, identify drop-off points, and translate behavioral analytics into prioritized experience improvements. Define what “good” looks like across every digital booking touchpoint—establish benchmarks, track progress, and escalate when performance is falling short of commercial expectations. Unified Digital Ecosystem & Cross-Platform Strategy Own the vision for a cohesive Virgin Voyages digital ecosystem—one where VirginVoyages.com, the Sailor App, and onboard digital screens feel like connected chapters of the same journey rather than separate products. Define the strategic connective tissue between pre-sail digital touchpoints and the onboard experience: how does the web experience set up the app experience? How do onboard digital screens extend the brand and drive ancillary conversion? How does the Sailor App deepen engagement before, during, and after the voyage? Partner with IT, Product, and Experience teams to ensure the technology roadmap supports the commercial and experiential vision—translating strategic intent into platform requirements without getting lost in technical detail. Ensure personalization and AI-powered capabilities are deployed in service of the commercial strategy—from intelligent recommendations and dynamic content to predictive personalization that makes every Sailor feel like the experience was built for them. Team Leadership, Roadmap Prioritization & Stakeholder Influence Lead, develop, and inspire a team of 4 Senior Managers and a total org of 12–15—setting a high bar for commercial thinking, creative ambition, and data-driven decision-making across every function. Own the digital enhancement roadmap across