Cloud9 is an AI-native luxury short-term rental operator. We turn long-term luxury rentals into exceptional short-term stays, delivering hotel-grade quality to guests while helping property managers unlock the top-line potential of their buildings. We run 60+ units across 13 Class-A residential buildings in Chicago, and we're expanding city by city across the U.S. We exist to reinvent hospitality with AI-driven execution.
How we work: a small, AI-native team that builds 4:1 leverage. You work alongside Claude every day; AI is a co-pilot, not a buzzword. The team is distributed, some in Chicago, some in Latam. We move fast, decide fast, and cut politics. We don't hire to fill seats. We hire to pull levers that move numbers. Outcomes beat effort beats intentions.
We run on C.L.O.U.D.9, our culture operating system:
C · Customer Obsession. If they're not raving, we missed it.
L · Leadership Through Ownership. No passengers, only drivers.
O · Operational Excellence. How we do one thing is how we do everything.
U · Urgency With Intelligence. Act now, iterate later.
D · Do the Right Thing. Character over convenience.
9 · The 9x Mindset. 10% better is safe; 9x better is unforgettable.
Cloud9 generates raw material every day: the founder's takes, calls, talks, the company's stories. Almost none of it gets turned into content. We need someone to own that.
You'll own two brands on one engine: the Cloud9 company brand and Marcus's personal CEO brand. You turn long-form into short-form at volume. One talk becomes thirty posts. One call becomes a week of content. Across LinkedIn, X, YouTube, and short-form video.
This is a production role, not a strategy role. You make things and ship them. Daily.
You work with AI as your multiplier. AI slices, drafts, and repurposes. You own the voice, the taste, and what goes live.
What you'll ownThe waterfall. Long-form in, many short-form out. Every source mined for everything it's worth.
Volume. On-brand assets published every week, on both brands. Your number is the cadence.
Founder voice. Marcus's personal brand. You write so it reads like him, not like a press release.
Company brand. The Cloud9 identity, voice, and look. Consistent everywhere.
The production system. Capture to publish. Documented. Repeatable. Runs without anyone babysitting it.
Taste. What ships and what gets killed. Volume without a bar is noise.
What success looks likeDay 30. Brand and voice audit done. Production system stood up. First waterfalls shipped from existing raw material. Baseline audience and cadence numbers set.
Day 90. Consistent weekly cadence on both brands. Organic brand searches and direct-site traffic trending up. A documented pipeline anyone could run.
Month 12. [Owned audience = a real channel. Brand-search up X%. Cadence at Y assets/week.] The brand is a talent and demand magnet. The engine runs without the founder producing it.
What you'll needA portfolio of short-form video and content you personally made. Bring it. The portfolio matters more than the resume.
A content waterfall you've built and run: one long-form turned into many short-form across platforms.
Proof of volume. You've published at real cadence with a system, not in bursts.
The ability to write in someone else's voice. Founder voice, not corporate comms.
Heavy AI tool use. Claude or equivalent in your daily flow to produce at volume.
A point of view on brand. Taste you can defend.
Fluent English, written and spoken.
Strategists who don't produce. We hire makers.
One-off posters with no system.
Corporate-comms or press-release writers.
People who need a full brief before they can move.
People who think AI is beneath them, or who hide that they use it.
People who confuse reach with brand.
The brand function is unbuilt. You're not inheriting a machine, you're building one.
The founder is the primary subject. You'll work closely with Marcus and have to nail his voice fast.
This role likely starts as a paid contract / fractional engagement before it goes full-time. We test the work first.
You work alongside Claude. AI is the production multiplier, not a buzzword.
Distributed team. Some in Chicago. Some in Latam.
Decisions move at speed. Mediocre content gets cut faster.
If you want to own a number, move fast, and build with AI instead of around it, this is the place. Small team, real leverage, high standards, and the people who build the systems get to run them as we scale city by city. If you want a comfortable seat where effort counts more than outcomes, we are not it.
Cloud9 does not discriminate based on race, religion, color, national origin, gender (including pregnancy, childbirth, or related medical conditions), sexual orientation, gender identity, gender expression, age, status as a protected veteran, status as an individual with a disability, or other applicable legally protected characteristics.
Skills Required
- Portfolio of short-form video and content personally produced
- Built and run a content waterfall that turns long-form into many short-form assets
- Proven volume: published at a sustained cadence with a documented system
- Ability to write in someone else's voice, specifically the founder's voice
- Heavy daily use of AI tools (Claude or equivalent) in production workflow
- Defendable point of view on brand and strong editorial taste
- Fluent English, written and spoken
- Experience creating and publishing short-form video across LinkedIn, X, and YouTube
What We Do
About Cloud9 At Cloud9, we are on a mission to revolutionize the hospitality industry. By transforming long-term luxury rentals into exceptional short-term experiences, we deliver unparalleled quality and service to our guests. At the same time, we empower property managers to unlock the full potential of their properties, maximizing their buildings top line. Our vision? To become the go-to solution for property managers across the U.S. We're expanding city by city, bringing our innovative approach and passion for excellence to new markets and communities. What makes Cloud9 truly unique isn’t just our commitment to service—it's our people. We believe in the power of teamwork to drive success. Whether you're a guest, a partner, or part of our team, you'll find collaboration, trust, and shared purpose at the heart of everything we do. Why Join Us? Cloud9 is more than a company; it’s a community of dreamers, doers, and problem-solvers who share a common goal: delivering excellence in every interaction. If you’re passionate about innovation, value teamwork, and want to grow in a fast-paced environment, Cloud9 is the place for you. Together, we’re not just building better stays—we’re building a better way forward for the hospitality industry.
