Head of Marketing
Company: Valhalla Services
Location: Chicago, IL (Remote)
Type: Full-time
Remote: Yes
Posted: 2026-04-14
About this role
About Monarch Collective & the opportunity
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 opport...