Executive Assistant to CEO - Operations & Automation

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TYPE OF WORK

Full Time

SALARY

$18,000+ annual cash pay + other $$$

HOURS PER WEEK

TBD

DATE UPDATED

Sep 26, 2026

JOB OVERVIEW

Executive Assistant to CEO - Operations & Automation

Remote - Philippines | Full-time | $18,000+ Annual cash pay | U.S. Eastern Time

This is not a traditional virtual assistant position. We're looking for a capable and ambitious person to work directly with the CEO of a fast-growing U.S.-based healthcare AI startup working with leading organizations in the U.S. and internationally. The CEO works across customers, investors, partnerships, recruiting, conferences, international opportunities, and company strategy.

Your mission: multiply the CEO's effectiveness. You'll help make sure important things never fall through the cracks, anticipate what needs to happen next, own follow-through, and use AI and automation to eliminate repetitive work.
We don't want someone who waits for tasks. We want someone who eventually sees what needs to happen before the CEO asks.

For an exceptional performer, this role can grow beyond Executive Assistant responsibilities into Chief-of-Staff-level responsibilities eventually. This is a long-term career opportunity, not a temporary VA position.

What you'll own:
- Calendar management and scheduling
- Inbox organization and important follow-ups
- Tracking commitments and next steps from meetings
- Preparing concise CEO briefings before important meetings
- Researching executives, companies, customers, and opportunities
- Drafting professional emails and follow-ups
- CRM and relationship management
- Conference preparation and prioritization
- Travel planning and logistics
- Tracking CEO priorities and open items
- Following projects until they are actually completed

A question you should naturally ask yourself every day: “What can I take off the CEO's plate?” AI & Automation. We want someone who improves systems, not someone who manually repeats the same work forever.

You'll help create workflows such as:
- Meeting transcript → action items → follow-up drafts → CRM
- Upcoming meeting → executive/company research brief
- Inbox → priority identification and follow-up tracking
- Conference attendee list → researched and prioritized targets
- Commitments → reminders until completed
- Automated CRM updates
- Weekly CEO follow-up dashboard

You should be excited about tools such as ChatGPT, Claude, MS365, CRMs, and automation platforms. You don't need to know every tool already. We're looking for someone who can understand a problem, learn quickly, experiment, and figure things out.

You should be extremely organized. If someone says, “Let's reconnect in three months,” you make sure it happens three months later. You notice when something is falling through the cracks before anyone asks. If the CEO tells you: “Figure this out.” You research the problem, think through the options, recommend a solution, and move it forward.

We're looking for:
- 5+ years supporting a CEO, founder, or senior executive
- Excellent written and spoken English
- Experience supporting U.S.-based executives preferred
- Exceptional follow-through
- Strong judgment and prioritization
- High attention to detail
- Strong problem-solving ability
- Comfort using AI extensively
- Interest in automation and process improvement
- Ability to handle confidential information
- A desire to take on substantially more responsibility over time
Startup or healthcare experience is helpful but not required.
Ownership, intelligence, judgment, and follow-through matter more.

Schedule:
45 hrs/week, Monday to Friday. The role will primarily follow U.S. Eastern Time, approximately 9 AM–6 PM ET. You must already be comfortable working overnight hours from the Philippines. Schedules may occasionally change for important meetings or CEO travel, but this is not a 24/7 on-call position.

Compensation:
Total annual compensation package value: $30,000+.

$18,000+ annual cash pay, which includes a monthly fixed cash base + quarterly and year-end cash bonus. In addition to cash pay, you will receive startup stock options with an approximately $12,000 target grant value, subject to the company's equity plan. Equity is intended to provide meaningful long-term upside and alignment. For someone exceptional, responsibilities and compensation can grow significantly as the role evolves.

What success looks like, within 90 days:
- The CEO rarely needs to remember follow-ups
- Important relationships don't a ---------- go cold
- Meetings happen with proper preparation
- Commitments become tracked actions
- Important emails are handled quickly
- Information is organized and easy to retrieve
- Repetitive work is increasingly automated
- You're solving problems before being asked
Ultimately, we want the CEO to think: “I don't know how I operated without this person.”

How to apply:
Start your application with: "CEO100". We won't review applications without this.

Please send:
1. Your resume
2. A 2-minute Loom video introducing yourself and explaining why you're a strong fit
3. The most demanding CEO/founder/executive you've supported and what you personally owned
4. One example of something you caught and fixed before your executive asked
5. One example of how you've used AI or automation to improve your work
6. Confirmation that you can work 9:00 AM–6:00 PM U.S. Eastern Time
7. Whether you currently have another job or ongoing clients

Please don't send a generic cover letter.
We're much more interested in how you think, take ownership, and solve problems.

SKILL REQUIREMENT
Project Management Executive Assistance AI Automation
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