16 Content Writer jobs in Chicago

Salary: $52,000–$62,000, based on experience

Location: Chicago

Company: Mainland

Don’t Just Write Content. Find the Story.

Mainland is looking for a curious, ambitious writer who wants to become exceptional at interviewing people, identifying meaningful stories and turning complex ideas into content people genuinely want to read.

This is not a role built around rewriting press releases, filling a content calendar or generating generic articles with AI. You will interview entrepreneurs, franchise founders, executives and local business owners. You will be expected to ask thoughtful questions, uncover what makes each story matter and produce writing that is clear, accurate and compelling.

Mainland is transforming from a traditional agency into the premier franchise growth platform in the industry. Our writers do more than complete assignments. They help define the voice of our publications, strengthen our clients’ brands and create stories that influence how people think about business ownership and entrepreneurship.

What You’ll Do

• Interview founders, executives, franchisees and subject-matter experts.
• Research brands, industries, markets and business trends.
• Write feature stories, founder profiles, franchisee spotlights, thought-leadership articles and brand content.
• Develop strong headlines, subheads, leads and story structures.
• Find the meaningful angle instead of settling for the obvious one.
• Turn interviews, data and business information into engaging narratives.
• Write for Mainland’s publications and client platforms.
• Revise work based on direct editorial feedback.
• Maintain accuracy, clarity, voice and journalistic integrity.
• Manage multiple assignments and consistently meet deadlines.
• Use AI as a support tool for research, organization and editing—not as a replacement for reporting, judgment or original writing.
• Help publish and optimize completed stories when needed.

What Success Looks Like

You consistently produce polished stories that require minimal rewriting.

Your interviews uncover insights that were not apparent before the conversation.

Your headlines make people want to keep reading.

Your work is accurate, well structured and written in the appropriate voice.

You accept feedback without becoming defensive and apply it to the next assignment.

You take ownership of deadlines, communication and the quality of the final product.

Most importantly, your writing gets stronger over time.

You May Be a Great Fit If You

• Have professional experience in journalism, editorial, communications, content marketing or business writing.
• Are an excellent interviewer and an active listener.
• Know how to turn a conversation into a compelling story.
• Can make complicated business ideas understandable.
• Have strong grammar, research and fact-checking skills.
• Care about headlines, leads, structure and word choice.
• Are curious about entrepreneurship, franchising and business growth.
• Want direct feedback and clear performance expectations.
• Can work independently without becoming disconnected from the team.
• Take pride in doing more than what is technically required.

A journalism, English, communications or related degree is helpful, but the strength of your portfolio and your ability to think like a reporter matter more.

This Role Is Not for Everyone

This is not a content-factory position, and it is not a role for someone who wants AI to do the thinking.

You will be expected to conduct real interviews, complete meaningful research, meet deadlines and improve through consistent feedback. We move quickly, communicate directly and care deeply about the work we put into the world.

Someone looking for a low-accountability writing job may not enjoy Mainland.

Someone who wants to become a sharper interviewer, stronger storyteller and more valuable writer may thrive here.

Why Mainland

You will have the opportunity to interview entrepreneurs and business leaders from across the country, contribute to established and emerging publications, and develop a body of work that goes far beyond anonymous marketing copy.

You will also join Mainland during an important period of growth and reinvention. We are investing in our publications, our technology and the people capable of helping us build what comes next.

We are not simply looking for someone who can write.

• We are looking for someone who can find the story—and make people care about it.