Chief Marketing Officer, CMO; Remote

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

Chief Marketing Officer (CMO) | Stay’d | Vacation Rental Collective Company Overview

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.

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…