Remote Content Operations Jobs in Chicago, IL (NOW HIRING)

We're hiring an AI Editor to join a small core team that punches well above its weight - and has the opportunity to punch much harder still.

Rental Scale-Up (RSU) is the leading publication for short-term rental professionals, run day-to-day by a team of two. We move fast, decide quickly, and use AI aggressively to do the work that used to take teams of ten. But RSU doesn't sit in isolation. It's part of PriceLabs, a much larger organisation with a substantial content and marketing team, and the two are increasingly integrating. That means the surface area of this role is large: you'll operate within a tight core team, but the content ecosystem you influence - across brands, audiences, and channels - is not small.

We're looking for someone to raise our ceiling. Not a manager. Not an executor we need to train. A peer - already deep in AI-native content work, already thinking in systems, and ready for a role with real scope and real ownership.

A note on the title: "AI Editor" captures half of what this role is. The other half is editorial. This is not a pure AI-systems job. You need to be a strong journalist and content thinker first - someone who can read the news, spot the story, judge what matters, and shape it into work our readers trust. The AI expertise is what lets you do that at scale. If you've spent the last two years rebuilding how you work around AI and you come from a genuine content or editorial background, this is the role.

• Own content strategy end-to-end. Read the news, spot the story, decide the angle, ship the piece, measure what happened. You won't be handed briefs - you'll write them.
• Build the system, not just the output. Design workflows and automations that let a small team produce at the scale of a large one. If a task is being done manually more than twice, your instinct should be to ask why.
• Push our AI stack forward. Identify where we're still doing things the old way. Prototype new approaches. Bring tools and techniques we haven't tried yet.
• Publish across formats. Articles, newsletters, video, webinars, social. You won't personally do every step, but you'll own the standard for all of them.
• Help connect Rental Scale-Up and PriceLabs content. As the two brands' content operations integrate more closely, you'll shape how that works in practice - shared workflows, shared tooling, shared standards. This is where the scope really opens up.
• Measure what matters. Move past vanity metrics. Understand what actually drives readers to become customers, and optimise for that.

• 2+ years in digital content, SEO, content marketing, or a closely adjacent field. You've done the job long enough to have strong opinions about how it should be done.
• Editorial instincts, not just marketing instincts. You can tell the difference between a real story and filler. You can read a 40-page industry report and find the one thing that matters. You understand that trust with readers is built one honest piece at a time.
• Concrete, demonstrable AI expertise. We mean this specifically. Not "I use ChatGPT sometimes." We want to see the workflows you've built, the automations you've deployed, and the prompts you've iterated into production tools. In your application, tell us about a specific AI-enabled content system you've built and what it replaced.
• Systems thinker. You see content operations as a machine to be designed, not a checklist to be completed. You're comfortable with tools like n8n, Zapier, Make, or direct API work - and comfortable learning new ones quickly.
• Ambitious about scope. The core team is small by design. The opportunity isn't. If you want a role where your thinking can influence content operations across a much larger organisation, that's what this is.
• Comfortable getting hands dirty. Everyone on this team writes, edits, ships, and uploads things. The seniority is in the thinking, not the distance from the work.
• Comfortable with speed and ambiguity. We often decide on a Monday to change something, ship it on Tuesday, and evaluate on Wednesday. If that sounds stressful rather than energising, this isn't the right fit.
• Native or bilingual English.

• Experience in travel, hospitality, real estate, SaaS, or another B2B industry with a professional audience
• Background in journalism, newsroom operations, or publication-style content (as opposed to pure marketing content)
• Working knowledge of Claude Code, Cursor, or similar agentic coding tools
• Experience with headless CMS platforms (Sanity, Contentful, Strapi, etc.) - particularly migrations that preserved SEO equity

• 600K+ listings
• 160+ integrations
• 300+ globally remote team
• 70K+ customers worldwide
• 40% diversity

• SaasBoomi 2021
• The Shortyz 2020
• The Shortyz 2023
• STRive Awards 2025
• STRive Awards 2026

• Work with an industry-leading product that has thousands of customers worldwide, and our customers love the product! (NPS in the 70s, Customer reviews here)
• Work with a global team (18 countries and counting) of passionate individuals that accept open communication, empowerment, and a shared focus on customer success.
• We are a freemium product, so marketing leads the charge on customer acquisition.
• We are a remote-first organization and accept work from home as the norm.