Chief marketing officer, cmo (remote, us-based)

Chief Marketing Officer (CMO) Company Overview Stay'd is a rapidly growing vacation rental collective built to redefine hospitality at scale. We 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 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 ownership, speed, and continuous improvement. What We're Looking For • 7–10+ years of marketing experience, with senior leadership experience • Proven track record of: • Scaling paid media (PPC + Meta) profitably • Building and optimizing funnels and conversion systems • Driving direct bookings in hospitality, travel, or similar industries • Generating qualified inbound leads (real estate / homeowner acquisition is a plus) • Strong experience building and leading teams—this is critical for success in this role • A true self-starter who takes ownership and drives initiatives forward without hand-holding • Someone who embodies our core values: Solutions Oriented, Move Fast, No Ego • Strategic thinker who can also execute when needed • Deep understanding of performance marketing, attribution, and growth metrics • Experience in vacation rentals, hospitality, real estate, or marketplaces is a strong plus Compensation $100,000 – $145,000 OTE. Performance-based incentives tied to growth metrics (direct bookings, lead volume, CAC targets, etc.) Why Join Stay'd • Opportunity to build and lead the marketing function at a high-growth company • Direct impact on revenue, brand, and expansion strategy • Work across multiple brands and markets at scale • High-autonomy role with real ownership • Be part of building a dominant hospitality platform How to Apply If you've built and scaled marketing systems that drive real revenue—not just impressions—we want to hear from you. Please include: • Examples of campaigns you've scaled • Metrics you've driven (ROAS, CAC, conversion rates, etc.) • Experience building teams and marketing infrastructure