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 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 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 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