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 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