Director of Marketing – Now Accepting Applications

Employment Type: Full-Time (Contract-to-Hire Option Available)

We’re a boutique, high-touch real estate team in Chicago specializing in luxury, historic, and architecturally significant properties. With a small but mighty team, we deliver a level of service and market expertise that keeps our clients coming back—and referring us again and again. Now, we’re looking for a Director of Marketing to take our brand presence and business growth to the next level.

This is not a “just keep the social media running” role. We’re looking for a strategic, creative self-starter who can dream big, execute flawlessly, and wear multiple hats in a fast-moving, collaborative environment. You’ll report directly to the team lead, work closely with our Director of Operations, and have the freedom to make a measurable impact on our brand’s reach and reputation.

What You’ll Do

• Develop and execute a comprehensive marketing strategy to grow brand awareness and generate new business.
• Manage our social media presence—both organic and paid—across all platforms (Instagram, Facebook, LinkedIn, YouTube, etc.).
• Create engaging content (photo, video, copy) aligned with our brand voice, with a strong emphasis on, but not limited to, storytelling around properties, neighborhoods, and the client experience.
• Manage and optimize paid ad campaigns, including budget allocation, targeting, and performance analysis.
• Oversee marketing for new listings, including social campaigns, property spotlights, and community outreach.
• Utilize analytics to measure campaign success, prepare reports, and adjust strategies to maximize ROI.
• Keep our brand presence fresh, consistent, and luxury-aligned across all channels.
• Stay on top of marketing trends—especially in luxury real estate—and proactively bring new ideas to the table.

What We’re Looking For

• Proven experience in marketing—real estate experience is a huge plus, but not required.
• A creative thinker with strong storytelling skills, both visual and written.
• Proficiency with marketing tools and platforms (social scheduling tools, Meta Business Suite, Canva or Adobe Creative Suite, etc.).
• Strong understanding of social media algorithms, engagement strategies, and paid advertising best practices.
• Comfortable analyzing data, reporting results, and making strategy adjustments.
• Experience with video content creation or listing video marketing is a plus.
• Highly organized, self-motivated, and able to take initiative in a small-team environment.
• Thrives in a hybrid role—able to work independently remotely, but also attend in-person shoots, events, and meetings in Chicago.

Why Join Us

• The opportunity to directly shape the marketing voice of a recognized Chicago real estate brand.
• Creative freedom to implement your ideas and see the direct impact on business growth.
• Collaborative, supportive team culture with high standards and a commitment to excellence.
• Flexible contract-to-hire pathway for the right fit.

Compensation: Competitive, commensurate with experience, plus potential performance and/or project-based incentives.

Interested?

• Please email your resume to kevin(at)alexwolking(dotted)com.