Executive Assistant / Ops Coordinator (Path to Chief of Staff) — AI-Powered Founder Support

I'm a serial entrepreneur running multiple businesses and projects at once now for over 25 years. I need one sharp, organized, deeply trustworthy person to help me run my world — starting as my Executive Assistant and Operations Coordinator, and growing into my Chief of Staff as we build trust over time.

This is not a typical VA role where you wait for tasks. I'm looking for someone who thinks ahead, catches the things I miss, and takes ownership of keeping my projects, calendar, and commitments on track. Someone I can eventually drop into an email thread or a project and trust to represent me well. Someone is well-organized and assertive and make sure I am on top of everything.

You will work closely with me every day. Over time, as you prove yourself, you'll get more access, more responsibility, and more pay. The person who grows into this role will become one of the most important people in my operation.

WHAT YOU'LL DO (starting scope)
- Manage my calendar — scheduling, rescheduling, protecting my focus time, preventing conflicts
- Keep my projects organized and on track — you'll be my system for "what's next, what's stalled, what's due"
- Research — markets, tools, people, options for decisions I need to make
- Book travel — flights, hotels, logistics, itineraries
- Use AI tools (especially Claude) to automate and speed up as much as possible
- Social media content writing for one of my companies
- Draft documents, summaries, and communications for my review
- Track follow-ups and make sure nothing falls through the cracks

WHAT YOU'LL GROW INTO (as trust builds)
- Following up with people on my behalf in email and chat threads
- Representing me in coordination with my team and partners
- Owning entire workflows end-to-end
- Helping manage other tea ---------- mbers
- True Chief of Staff responsibilities

WHO YOU ARE
REQUIRED:
- Excellent written and spoken English (C1 or higher — you'll be communicating on my behalf)
- Genuinely proficient with AI tools, especially Claude — you actively use AI to work faster, not just occasionally
- Strong project management instincts — you naturally track, prioritize, and follow up without being reminded
- Obsessively organized and detail-oriented — you're the person who never lets things slip
- High discretion and integrity — you'll handle confidential information and you understand why that matters
- An eye for design — you can make a document, deck, or system look clean and professional
- Available full-time with overlap around 8 am to 4 pm PST US Pacific business hours
- Reliable internet and power with backups

STRONGLY PREFERRED:
- Previous experience as an Executive Assistant, Chief of Staff, Operations Manager, or similar role to a founder or executive
- Experience managing multiple projects or workstreams simultaneously
- Familiarity with tools like Notion, Google Workspace, project management software, and automation tools
- Experience using AI agents or automation workflows (Zapier, Make, AI assistants, etc.)

NICE TO HAVE:
- Experience supporting a founder running multiple businesses
- Light graphic design skills (Canva, Figma, or similar)
- A track record of long-term roles (you stay and grow, you don't hop)

WHAT YOU GET
- $250-$350 USD/month to start for 20 hours of work and will grow to up to 40 hours of work and higher pay over time and more responsibilities, based on experience (paid 2x/month via Wise, Payoneer, or PayPal)
- A clear, real path to higher pay and a Chief of Staff title as you prove yourself — this is not a dead-end VA job
- Direct daily work with a founder — you'll learn how multiple businesses are run from the inside
- 13th-month bonus
- Paid time off after 3 months
- Performance reviews with raise considerations at 90 days, then every 6 months
- Long-term stability — I'm looking for someone for years, not months. The right person becomes irreplaceable.

HOW TRUST AND ACCESS WORK

I want to be upfront about something: I won't hand a new hire access to my sensitive emails and chats on day one. Trust is earned through how you handle the work.

You'll start with calendar, research, travel, and project tracking. As you demonstrate good judgment and discretion over your first 30-60 days, I'll progressively give you more access and more responsibility — including following up on my behalf and handling sensitive matters. By 90 days, the right person is operating as my right hand.

If you're the kind of person who understands why trust works this way, you're exactly who I'm looking for. If you expect full access immediately, this isn't the right fit.

HOW TO APPLY

Send a message with ALL of the following. Applications missing any item will not be reviewed:
1. SUBJECT LINE: "Chief of Staff Path — [Your Name]"
2. A 4-6 sentence introduction. Tell me who you are, what you've done, and why THIS role — not a generic cover letter. I can tell the difference instantly.
3. Your monthly salary expectation in USD.
4. Confirm you can work in the same hours daily overlapping US Pacific Time 8am-4pm (roughly 11pm-4am your time). Be honest about whether this works long-term.
5. ANSWER ALL SIX OF THESE QUESTIONS:

Q1: Describe a time you supported a busy person (a boss, founder, or executive) and caught something important they were about to miss. What was it, and what did you do?

Q2: How do you currently use AI tools like Claude or ChatGPT in your work? Give me one specific example of something you automated or sped up using AI. Be specific — I want to understand how you actually think about using these tools.

Q3: I have 13 different projects running at once. Some are urgent, some are important-but-not-urgent, some are stalled waiting on other people. If you were my Ops Coordinator, how would you keep track of all of them and d ---------- what to surface to me each day? Describe your system in 4-6 sentences.

Q4: You have access to my calendar and inbox. You see an email from someone I've never mentioned, marked urgent, asking me to confirm a payment by end of day. I'm in meetings and unreachable for 3 hours. What do you do? Walk me through your exact thinking.

Q5: Tell me about a time you were trusted with confidential or sensitive information. How did you handle it, and how do you think about discretion in your work?

Q6: This role starts as an Executive Assistant and grows into a Chief of Staff. Where do you want to be in 2-3 years, and why does this growth path appeal to you?

6. Attach a 1-2 minute video of yourself (phone is fine) answering this one question: "Tell me about the busiest or most complex situation you ever had to organize, and how you kept it under control." Be specific and concise. Share a Google Drive link with the video.

7. (OPTIONAL but encouraged) Share a link to anything you've made that shows your eye for organization or design — a Notion workspace, a document, a deck, a system you built, a Canva design. Anything that shows how you make things clean and clear.

I'll respond to qualified candidates within 5-7 business days. If you don't hear fro ---------- in 10 business days, I've moved forward with others — and I'm grateful for the time you put into applying.

NEXT STEPS IF SELECTED

1. Initial 30-minute video interview with me
2. A paid trial assignment ($20 USD) — a real task that shows me how you work
3. Final decision and onboarding within 2-4 weeks of applying

I'm looking for someone special. If that's you, I'd love to hear from you.