Head of Marketing

Chicago, IL (Remote)

Salary Not AvailableSenior Level7+ years expFull time

Posted 3 months ago

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Job Summary

Drive marketing leadership across guest and owner acquisition for Monarch Collective, owning a seven-figure budget, building a scalable marketing OS, and embedding AI into daily workflows.

  • Own cross-channel strategy and KPI-driven results for guest and owner acquisition.
  • Must-have: seven-figure budget ownership with clear ROI and channel trade-offs.
  • Standout: proven AI-enabled marketing acceleration and leadership of a small, high-performance team.

Job Description

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.
  • There\'s a KPI framework in place for guest marketing and owner marketing that is adopted and value add.
  • Direct bookings are up, and you can clearly explain what drove it. Owner leads are better – more volume, better quality, and a repeatable system behind it.

Requirements

  • 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.

Preferred

  • 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.