Chief Marketing Officer, CMO; Remote

Position: Chief Marketing Officer, CMO (Remote, US-Based) Chief Marketing Officer (CMO) | Stay’d | Vacation Rental Collective Company Overview Stay’d is a rapidly growing vacation rental collective built to redefine hospitality bring together high-performing local brands under one umbrella, combining best-in-class operations, design, and revenue management to create standout guest experiences and stronger returns for homeowners. With thousands of properties spanning multiple markets, Stay’d is building a scalable platform designed to unify brands, systems, and performance while maintaining a high-touch, locally driven experience. We’re not a marketplace—we’re operators. And we’re building something meant to last. The Opportunity We are looking for a proven Chief Marketing Officer to architect and lead our entire marketing engine from the ground up. This is a builder role with a clear mandate to design, implement, and scale a best-in-class marketing function. We are looking for an “A player” who can bring structure, clarity, and rigor to a fast-growing, multi-entity environment. You will be responsible for creating, executing, and scaling a multi-channel marketing machine that drives: • Direct bookings • Qualified homeowner leads • Brand expansion across multiple markets Just as important as your technical expertise is your ability to build, lead, and develop a high-performing team. This role requires someone who can set the vision, create structure, and elevate the people around them. We are also looking for someone who is a true self-starter and aligns deeply with how we operate. Our culture is built around three core values: • Solutions Oriented — you solve problems, not point them out • Move Fast — you operate with urgency and bias toward action • No Ego — you collaborate, take feedback, and prioritize the team over individual credit You will own strategy, team development, and performance. What You’ll Own Cohesive Brand Strategy (Across All Brands) • Develop and implement a unified brand strategy across multiple brands and markets • Ensure consistent positioning, messaging, and visual identity while preserving local brand strengths • Elevate Stay’d into a recognizable and trusted umbrella brand Growth & Revenue Strategy • Build and execute a full-funnel marketing strategy focused on direct booking growth and owner acquisition • Develop scalable systems that drive predictable lead flow across all brands within Stay’d • Establish CAC, LTV, and ROI benchmarks across channels and continuously optimize Paid Media (PPC Meta) • Oversee and optimize Google PPC, Meta ads, and retargeting strategies • Scale campaigns profitably with a strong focus on conversion, not just traffic • Lead internal and/or external media buying resources Funnel & Conversion Optimization • Build high-converting landing pages, funnels, and lead capture systems • Optimize the full customer journey—from click to booking / signed owner • Implement A/B testing frameworks to improve conversion rates Direct Booking Engine • Lead initiatives to reduce OTA reliance and increase direct booking share • Improve website UX, booking flow, and conversion strategy • Implement CRM, email, and remarketing strategies to maximize repeat bookings Lead Generation (Homeowners) • Build and scale systems for owner lead generation • Execute targeted campaigns across digital, outbound, and offline channels • Develop messaging that converts homeowners at a high rate Email, CRM & Lifecycle Marketing • Build and optimize email marketing, automations, and nurture sequences • Implement segmentation strategies for both guests and homeowners • Increase lifetime value through retention and re-engagement SEO & Organic Growth • Develop and execute a long-term SEO strategy • Build content, backlink, and local SEO systems to drive organic traffic • Position Stay’d and its brands as category leaders Offline & Mailers • Oversee direct mail campaigns and local marketing initiatives • Integrate offline channels into broader funnel strategy • Track attribution and performance across campaigns Team Building & Leadership • Build and lead a high-performing marketing organization across: • Paid Media • Content / SEO • Email / CRM • Creative • Hire, mentor, and develop top talent • Establish KPIs, reporting structures, and accountability • Create a culture of…