Chief Marketing Officer, CMO

Chief Marketing Officer (CMO) Stay'd | Vacation Rental Collective 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 bookingsQualified homeowner leadsBrand 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 outMove Fast – you operate with urgency and bias toward actionNo 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 marketsEnsure consistent positioning, messaging, and visual identity while preserving local brand strengthsElevate 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 acquisitionDevelop scalable systems that drive predictable lead flow across all brands within Stay'dEstablish CAC, LTV, and ROI benchmarks across channels and continuously optimize Paid Media (PPC + Meta) Oversee and optimize Google PPC, Meta ads, and retargeting strategiesScale campaigns profitably with a strong focus on conversion, not just trafficLead internal and/or external media buying resources Funnel & Conversion Optimization Build high-converting landing pages, funnels, and lead capture systemsOptimize the full customer journey—from click to booking / signed ownerImplement A/B testing frameworks to improve conversion rates Direct Booking Engine Lead initiatives to reduce OTA reliance and increase direct booking shareImprove website UX, booking flow, and conversion strategyImplement CRM, email, and remarketing strategies to maximize repeat bookings Lead Generation (Homeowners) Build and scale systems for owner lead generationExecute targeted campaigns across digital, outbound, and offline channelsDevelop messaging that converts homeowners at a high rate Email, CRM & Lifecycle Marketing Build and optimize email marketing, automations, and nurture sequencesImplement segmentation strategies for both guests and homeownersIncrease lifetime value through retention and re-engagement SEO & Organic Growth Develop and execute a long-term SEO strategyBuild content, backlink, and local SEO systems to drive organic trafficPosition Stay'd and its brands as category leaders Offline & Mailers Oversee direct mail campaigns and local marketing initiativesIntegrate offline channels into broader funnel strategyTrack attribution and performance across campaigns Team Building & Leadership Build and lead a high-performing marketing organization across:Paid MediaContent / SEOEmail / CRMCreativeHire, mentor, and develop top talentEstablish KPIs, reporting structures, and accountabilityCreate a culture of ownership, speed, and continuous improvement What We're Looking For 7–10+ years of marketing experience, with senior leadership experienceProven track record of:Scaling paid media (PPC + Meta) profitablyBuilding and optimizing funnels and conversion systemsDriving direct bookings in hospitality, travel, or similar industriesGenerating qualified inbound leads (real estate / homeowner acquisition is a plus)Strong experience building and leading teams—this is critical for success in this roleA true self-starter who takes ownership and drives initiatives forward without hand-holdingSomeone who embodies our core values: Solutions Oriented, Move Fast, No EgoStrategic thinker who can also execute when neededDeep understanding of performance marketing, attribution, and growth metricsExperience in vacation rentals, hospitality, real estate, or marketplaces is a strong plus Compensation $100,000 – $145,000 OTEPerformance-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 companyDirect impact on revenue, brand, and expansion strategyWork across multiple brands and markets at scaleHigh-autonomy role with real ownershipBe 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 scaledMetrics you've driven (ROAS, CAC, conversion rates, etc.)Experience building teams and marketing infrastructure