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:
- 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