Role Description
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. You will be responsible for creating, executing, and scaling a multi-channel marketing machine that drives:
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Direct bookings
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Qualified homeowner leads
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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:
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Solutions Oriented – you solve problems, not point them out
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Move Fast – you operate with urgency and bias toward action
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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
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Cohesive Brand Strategy (Across All Brands)
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Develop and implement a unified brand strategy across multiple brands and markets
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Ensure consistent positioning, messaging, and visual identity while preserving local brand strengths
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Elevate Stay'd into a recognizable and trusted umbrella brand
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Growth & Revenue Strategy
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Build and execute a full-funnel marketing strategy focused on direct booking growth and owner acquisition
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Develop scalable systems that drive predictable lead flow across all brands within Stay'd
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Establish CAC, LTV, and ROI benchmarks across channels and continuously optimize
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Paid Media (PPC + Meta)
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Oversee and optimize Google PPC, Meta ads, and retargeting strategies
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Scale campaigns profitably with a strong focus on conversion, not just traffic
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Lead internal and/or external media buying resources
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Funnel & Conversion Optimization
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Build high-converting landing pages, funnels, and lead capture systems
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Optimize the full customer journey—from click to booking / signed owner
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Implement A/B testing frameworks to improve conversion rates
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Direct Booking Engine
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Lead initiatives to reduce OTA reliance and increase direct booking share
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Improve website UX, booking flow, and conversion strategy
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Implement CRM, email, and remarketing strategies to maximize repeat bookings
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Lead Generation (Homeowners)
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Build and scale systems for owner lead generation
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Execute targeted campaigns across digital, outbound, and offline channels
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Develop messaging that converts homeowners at a high rate
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Email, CRM & Lifecycle Marketing
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Build and optimize email marketing, automations, and nurture sequences
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Implement segmentation strategies for both guests and homeowners
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Increase lifetime value through retention and re-engagement
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SEO & Organic Growth
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Develop and execute a long-term SEO strategy
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Build content, backlink, and local SEO systems to drive organic traffic
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Position Stay'd and its brands as category leaders
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Offline & Mailers
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Oversee direct mail campaigns and local marketing initiatives
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Integrate offline channels into broader funnel strategy
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Track attribution and performance across campaigns
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Team Building & Leadership
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Build and lead a high-performing marketing organization across:
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Paid Media
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Content / SEO
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Email / CRM
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Creative
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Hire, mentor, and develop top talent
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Establish KPIs, reporting structures, and accountability
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Create a culture of ownership, speed, and continuous improvement
Qualifications
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7–10+ years of marketing experience, with senior leadership experience
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Proven track record of scaling paid media (PPC + Meta) profitably
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Building and optimizing funnels and conversion systems
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Driving direct bookings in hospitality, travel, or similar industries
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Generating qualified inbound leads (real estate / homeowner acquisition is a plus)
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Strong experience building and leading teams—this is critical for success in this role
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A true self-starter who takes ownership and drives initiatives forward without hand-holding
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Someone who embodies our core values: Solutions Oriented, Move Fast, No Ego
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Strategic thinker who can also execute when needed
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Deep understanding of performance marketing, attribution, and growth metrics
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Experience in vacation rentals, hospitality, real estate, or marketplaces is a strong plus
Compensation
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$100,000 – $145,000 OTE
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Performance-based incentives tied to growth metrics (direct bookings, lead volume, CAC targets, etc.)
Benefits
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Opportunity to build and lead the marketing function at a high-growth company
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Direct impact on revenue, brand, and expansion strategy
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Work across multiple brands and markets at scale
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High-autonomy role with real ownership
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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:
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Examples of campaigns you've scaled
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Metrics you've driven (ROAS, CAC, conversion rates, etc.)
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Experience building teams and marketing infrastructure