Head of Marketing

VALHALLA SERVICES LLC • Chicago, IL

18h

About The Position

Monarch Collective is a national vacation rental management platform – we acquire, operate, and scale local vacation rental brands across the U.S. Each brand keeps its local identity: the relationships, the reputation, the market knowledge. Behind them is a centralized platform with a specialized infrastructure — including growth marketing, revenue management, data and analytics, finance, and operations. Founded in 2022, the model is successful and growing – with twenty-one brands across major U.S. vacation markets and growing – and we're just getting started.

We have an active acquisition pipeline to keep growing. Every deal adds new brands, new homeowners, and more scale to the platform. This is a company building toward something much larger than where it is today, and we believe marketing is one of the biggest levers to get there.

We are looking for a Head of Marketing to own performance of the function across the entire Monarch portfolio. The role will have two mandates: drive profitable direct bookings on the guest side, and generate quality homeowner leads that bring new inventory into our brands.

You'll set the strategy, define the target customers, build the playbooks, and own the results. A big part of this role is working across a portfolio of local brand operators who know their markets well. Your job is to earn their trust, give them tools that work, and raise the bar on what their marketing efforts can do.

We intentionally operate lean and are not building a large marketing department. Our goal is a small, high-caliber team that consistently outperforms its size – and we believe AI is a key enabler of that advantage.

We want someone who's already using AI to do things faster and better – whether that's replacing agency work, automating reporting, generating content, or running tests that would've taken more resources and time. The right person will look at our current setup and immediately see opportunities to operate more effectively with the resources we have.

Requirements

• You bring 7+ years of relevant experience, with a track record of increasing ownership and impact over time.
• You’ve driven real business outcomes through marketing – revenue, leads, efficiency, ROI. Not just impressions or brand awareness decks.
• You’re analytically sharp. Funnels, attribution, CAC, conversion, and resource allocation are second nature to you – and you use them to make decisions, not just report on them.
• You’ve owned and deployed a seven-figure marketing budget with intention. You can clearly articulate where you invested, why, and the trade-offs you made across channels, agencies, and in-house builds.
• You’ve built or led a marketing function through a growth phase – hiring, systems, and stack selection – with a focus on creating leverage, not just adding resources.
• You’ve operated in multi-brand, multi-location, or distributed environments and know how to execute without relying on top-down authority.
• You’re a builder. You’d rather design the system than inherit one, and you’re comfortable creating clarity where it doesn’t yet exist.
• You operate as a player–coach. You’re willing to stay close to the work while building and leading a high-performing function.
• You’re already leveraging AI in a meaningful way – not just exploring it. You can point to specific examples of how it has expanded your capabilities, improved speed, or driven better outcomes.

Nice To Haves

• Experience in hospitality, travel, vacation rentals, property management, marketplaces, or home services is a plus. We place greater weight on how you think and execute than on your prior industry experience though.

Responsibilities

• Marketing strategy and results across both guest and owner acquisition.
• Direct booking performance: SEO, PPC, email, lifecycle, website conversion, and any other channels that make sense as we evolve.
• Owner lead generation, working closely with local GMs and sales teams to make sure leads convert – quality, over quantity is important here.
• Build and establish the marketing operating system: KPIs, reporting, dashboards, weekly rhythms.
• Manage a seven-figure marketing budget – including agency and vendor decisions. What's working , what's not, and where AI or internal work gets a better result for less cost.
• Drive AI adoption across marketing as a core part of how the team works every day.
• Lead and manage a small team, creating a high performance culture.
• Build trusted relationships across the portfolio. The brand leaders need to see you as their marketing thought partner and leader, not someone with mandates for mandates sake.

What This Job Offers

• Job Type: Full-time
• Career Level: Manager
• Education Level: No Education Listed