Any
$5-$10 per hour
40
Jan 19, 2026
The Mission
We are looking for a "Force Multiplier." You aren't just here to manage a calendar; you are here to build the systems that allow our business to scale. You will act as the right hand to leadership, handling high-level administrative tasks while proactively identifying and executing growth opportunities.
If you are a self-learner who thrives in the "controlled chaos" of a startup and moves at a 10x pace, this is your role.
Key Responsibilities
1. Strategic Operations (The Growth)
System Building: Identify bottlenecks in our current workflow and implement automated solutions (CRM setups, AI integrations, or project management boards).
Market Research: Perform deep-dive research on potential acquisitions (like hospitality properties), city regulations, and competitor movements.
Growth Execution: Assist in managing lead generation pipelines and high-level outreach to investors or partners.
2. Executive Support (The Admin)
High-Stakes Coordination: Manage complex scheduling and "gatekeep" the executive’s time to ensure focus on high-leverage activities.
Document Management: Oversight of legal filings, contract renewals, and compliance documents.
Communication: Draft high-impact correspondence for investors, government officials, and key stakeholders.
The Profile: Who You Are
The "Swiss Army Knife": You can jump from a high-level strategy meeting to a tedious spreadsheet without losing
Radical Autonomy: You don't ask "What should I do today?" You say "Here is what I did, why I did it, and what I’m doing next."
Tech Native: You are an expert at using tools like Notion, HubSpot, Slack, and AI (ChatGPT/Claude) to work 5x faster than a traditional assistant.
Fast-Paced & Precise: You understand that in a startup, "Done is better than perfect," but in admin, "Accuracy is non-negotiable." You know when to apply which.
Qualifications
2+ years in a startup environment or as a high-level Executive Assistant/Chief of Staff.
Proven track record of improving a business process (saving time or money).
Exceptional written communication—you can sound like a CEO, a lawyer, or a salesperson depending on the audience.
Ability to work in a 100% remote, asynchronous environment.
The "Test" (To Apply) - ANSWER THIS QUESTIONS BY RECORIDNG YOURSELF.
In your application, please include:
One specific example of a time you taught yourself a new software or skill in 24 hours to solve a problem.
A brief summary of what you believe is the biggest administrative challenge for a small business trying to scale quickly.
Your favorite tool for automation and why.
The "Emergency" Test: If I disappear for 4 hours on your first day because of an emergency, and I haven't given you a task list yet, what do you do with that time?
The Problem Solver: Tell me about a time you saw a problem at work that wasn't "your job" to fix, but you fixed it anyway. What was the outcome?
The Self-Teacher: When you are faced with a task you have zero idea how to complete, what is your step-by-step process for getting it done without asking me for help?
The Anticipator: In your last role, what was something you did that made your boss’s life significantly easier before they even asked you to do it?
The Resilience Check: Tell me about a time you failed at a task or a project. How long did it take you to pivot, and what did you do the very next morning?
The Blunt Feedback: We move very fast here and I am often very direct. If I told you to "scratch everything you just did and start over," how would you handle that internally and externally?
The Brute Force Win: What is a professional goal you set for yourself in the last year that you hit purely through "brute force" and sheer hard work?
The Boring Task: What is the most tedious or repetitive task you’ve ever had to do, and how did you keep yourself motivated to do it perfectly every time?
The Resourcefulness: Describe a time you had to "beg, borrow, or steal" resources (legally!) to get a project across the finish line on a tight budget or deadline.
The Pitch: Why should I hire you over someone who has 10 more years of experience but maybe less "hunger" than you do?