About Us Our mission to revolutionize the hospitality industry. We exist to reinvent hospitality with AI-driven execution. By transforming long-term luxury rentals into exceptional short-term experiences, we deliver unparalleled quality and service to our guests. We empower property managers to unlock the full potential of their properties, maximizing their buildings top line. Our vision is 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. We believe in teamwork, collaboration, trust, and shared purpose at the heart of everything we do. We don’t hire to fill seats. We hire to pull levers that move numbers. Outcomes effort intentions. Our core values are speed, meritocracy, accountability, and execution . About The Role At Cloud9, we’re building a profitable, fast-moving business at the intersection of AI and revenue operations. We’re looking for someone to work directly with our founder — not as a traditional Executive Assistant, but as a high-leverage operator who can manage, optimize, and automate how the CEO works. This role is equal parts execution, systems thinking, and AI experimentation. If you’re the type of person who sees a manual process and immediately thinks “this should be automated,” you’ll thrive here. What You’ll Do Own the CEO’s operating system Manage calendar, scheduling, and priorities Handle inbox and communications with speed and judgment Ensure nothing falls through the cracks Run and improve daily operations Support task and workflow management (ClickUp and other tools) Track priorities and ensure execution across ongoing projects Bring structure to a fast-moving, sometimes ambiguous environment Automate everything that can be automated Identify repetitive workflows and eliminate manual work Build and maintain automations using AI tools (especially Claude) Continuously improve how we operate through AI Act as a problem solver and operator Take ownership of ad hoc projects directly from the CEO Move quickly from idea → execution Fill gaps wherever needed to keep momentum high Grow into broader ownership Over time, take on more responsibility across operations Become a key extension of the CEO in running the company What We’re Looking For AI-native mindset You actively use tools like Claude (or similar) in your daily life You’re constantly experimenting and learning new tools You think in systems, prompts, and automations Speed + ownership You move fast and don’t wait for perfect instructions You take initiative and figure things out independently You have strong attention to detail and follow-through Curiosity and growth You’re constantly learning (inside and outside of work) You enjoy solving ambiguous problems You’re excited to grow into a larger operational role over time Strong communication skills Clear, concise, and thoughtful written communication Good judgment when handling sensitive or external interactions This role is NOT for you if You’re looking for a traditional Executive Assistant role You prefer clear instructions over figuring things out You’re not actively curious about AI or new tools You’re uncomfortable working in a fast-changing environment Why this role is different You’ll work directly with the CEO, every day You’ll learn how a profitable, AI-driven company operates from the inside You’ll build real systems — not just manage tasks You’ll develop AI, ops, and execution skills that compound quickly 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. Our Core Values Meritocracy – Performance is public, measurable, and rewarded. Execution – Doers win. Deliver fast, adjust faster. Radical Feedback – Real-time corrections, no politics. Championship Team – Only A-players stay. Mediocrity is cut. Cloud9 does not discriminate based upon race, religion, color, national origin, gender, sexual orientation, gender identity, age, status as a protected veteran, status as an individual with a disability, or other applicable legally protected characteristics. #J-18808-Ljbffr