Job Description
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.
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.
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
You’ll sit at the center of the CEO’s day-to-day — making things run faster, smoother, and smarter.
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 (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.