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 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