Chief Marketing Officer, CMO; Remote

Chief Marketing Officer, CMO (Remote, US-Based)

Cocoa Beach, Florida, United States Operations

Stay'd is a rapidly growing vacation rental collective built to redefine hospitality  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.

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

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.

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

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

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

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

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

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

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

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

Oversee direct mail campaigns and local marketing initiatives

Integrate offline channels into broader funnel strategy

Track attribution and performance across campaigns

• Build and lead a high-performing marketing organization across:
  • Paid Media
  • Content / SEO
  • Email / CRM
  • Creative
• Hire, mentor, and develop top…