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Summary: This is a senior individual contributor role to own the architecture and reliability of AI-native luxury short-term rental systems, working with AI as a co-pilot. Highlights: 1. Own architecture and reliability for guest-facing systems 2. Hands-on IC role with architectural authority, not people management 3. Build and scale with AI in a fast-moving, outcome-driven team **About Cloud9** ---------------- 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. **What this is** ---------------- Cloud9 runs luxury short\-term rentals across Chicago, and we're turning the operation into a platform (Pentice). The software exists and real guests use it every day: Lighthouse screens and checks guests in, Glass Bridge runs the front desk. It works. It is also fragile, split across separate services, and hard to see into when something breaks. We need someone to own that. Make it reliable. Make it observable. Then pull the separate services together into one backend that can run every building and every city we expand to. This is the senior technical seat. You own the architecture and the reliability number. You work alongside our founding engineer and a junior, and you report to me. You write code every day with AI as your multiplier, and you review everything before it reaches a guest. This is an IC role with architectural authority. It is not a people\-management job. If you want to stop coding and run a team, this isn't it. **What you'll own** ------------------- **Reliability of the guest\-facing systems.** Lighthouse and Glass Bridge stay up and recover fast. That number is yours. Today it's not good enough to trust, which is the whole reason this role exists. **The architecture.** One data model, one backend, the plan to get the separate services there without losing data or taking the apps down. **The migration.** Live production data, moved carefully, with backups and rollback. No "big bang." No lost bookings. **The reliability standard.** Error handling, retries, escalation, observability. What "ready" means on this team. You set the bar and the others build to it. **Keeping the airplane flying.** Guests check in through this software right now. Job one is it doesn't break while you rebuild underneath it. **What success looks like** --------------------------- **Day 30\.** You've audited both apps. There's one place to see logs, errors, and alerts across them. The team has a written definition of "ready" that means tested against failure, not "it ran once." Baseline reliability numbers are set. **Day 90\.** Reliability is good enough that we expand Glass Bridge past the three buildings it's stuck at. The first service is consolidated into the unified backend with a clean, no\-downtime migration. We didn't lose velocity to get there. **Month 12\.** \[One backend, the major services consolidated and observable. Glass Bridge live across buildings and into new cities. Uptime at X%, P1 incidents under N/month.] Production rarely breaks, and when it does it recovers fast. **Compensation** ---------------- \[Base, to confirm.] Variable strictly per the canonical Cloud9 Quarterly Bonus Plan (multiplicative: Company Performance × Personal Performance × your Target Quarterly Bonus). AI Fluency tie applies. Real numbers confirmed at offer. **What you'll need** -------------------- * Production systems you personally owned and kept running. Bring the reliability numbers. The track record matters more than the resume. * A real migration you ran: live data moved across systems without downtime or loss. Tell us how you de\-risked it. * Resilience as a habit. If we ask how you'd handle a fetch that fails for a non\-error reason, we want to hear retries, backoff, escalation, and observability before we finish the question. * Strong full\-stack TypeScript: React and Node, in production. GCP or comparable cloud. * SQL and NoSQL, REST/GraphQL, webhooks, third\-party integrations (Stripe, Guesty\-type APIs). * Heavy, disciplined AI tool use. Claude Code or Codex in your daily flow, and you review and test what it writes. You don't push agent code to prod unread. * Fluent English, written and spoken. We write decisions down. **Who this is not for** ----------------------- * Architects who don't code. This seat ships. * People who only know greenfield. We have live guests and fragile production, not a blank repo. * Anyone whose "done" means "it worked on my machine." That's the exact problem we're replacing. * People who push AI\-written code to production without reading it. * People who want to manage a team instead of building. The team is small and you're hands\-on. * Anyone who needs a big engineering org to land in. There isn't one yet. You help build it. **What's real about Cloud9 right now** -------------------------------------- I'd rather you self\-select out now than two weeks in. * **Production is fragile.** Glass Bridge is frozen at three buildings because rollouts broke and I stopped trusting "it's ready." Fixing that trust is the job. * **The last person in this seat didn't work out.** We parted ways. I'm telling you because the gap is real and it's why we're hiring. * **The team is small:** me, a founding engineer, a junior, and AI agents that write a lot of the code. You're the senior technical owner, not a manager with reports. * **I'm the product owner, and I'm not an engineer.** I build working prototypes myself and I can tell when something's broken, but I can't read the code. I need someone who owns the engineering truth and tells it to me straight. * **We move fast and decide fast.** Distributed team, some in Chicago, some in Latam. Hybrid in Bogotá. * **We're profitable and bootstrapped.** Nine years operating, real product\-market fit in a niche. No VC, no runway clock, but also no infinite budget. **Why Cloud9** -------------- 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.
