Chief Marketing Officer, CMO (Remote, US-Based)
Beachside VR, Florida, NY, United States
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
#J-18808-Ljbffr
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
#J-18808-Ljbffr