Executive & Personal Assistant / Personal Operations Manager

Executive & Personal Assistant / Personal Operations Manager

I am an orthodontist, small-business owner, husband, and father in California looking for one exceptional long-term assistant in the Philippines.
This is not a basic task-taking VA role.
I need someone who can help create order around a busy professional and family life: capture open loops, organize priorities, follow up, research, communicate, coordinate with employees and vendors, manage calendars and email workflows, and make sure important commitments do not disappear.
The right person will be proactive, organized, comfortable with ambiguity, and willing to respectfully challenge me when I am avoiding something important or getting distracted by lower-priority work.

Your first month

Start with three outcomes:

• turn incoming requests into clear next actions and follow-up
• maintain the calendar and protect time for work only the owner can do
• bring a small agreed set of business and family commitments through to completion

The first month is a paid mutual-fit period with weekly feedback. We will introduce responsibilities and access progressively; you are not expected to fix every practice or household process at once.

How the role can grow

Over time, help with research, vendor and appointment coordination, inbox cleanup, email triage, replies within agreed authority, recurring reminders, project follow-up and lightweight documentation. Coordinate with our existing team and remote assistant. You do not replace clinical judgment or automatically manage office staff.
You will not be expected to know orthodontics when you start.

What I am looking for

You should be:

• extremely organized
• reliable with strong follow-through
• proactive rather than waiting for detailed instructions
• comfortable making recommendations
• confident enough to respectfully challenge your employer
• excellent in written and spoken English
• comfortable making phone calls to U.S. businesses
• highly capable with technology
• experienced using AI tools such as ChatGPT or Claude
• discreet with confidential information
• thoughtful about security and privacy
• able to distinguish urgent from important
• comfortable working with imperfect information
• interested in a long-term role

I am specifically not looking for someone who asks me what to do at every step. I want someone who can say:
"Here is the problem, here is what I found, here is what I recommend, and here is what I need from you."

Schedule

Approximately 15–20 hours per week initially.
Our initial coverage target is at least two predictable hours each weekday within 9 AM–5 PM California/Pacific Time for calls, coordination and the short daily check-in. Please propose a sustainable window; we will agree exact hours before an offer. California daylight-saving changes must be reflected in the agreed schedule.
Remaining work may be asynchronous. This is not an all-day on-call role; urgent matters outside your agreed hours remain with the owners or designated onsite staff.

Compensation

$6–$10 USD/hour depending on experience and demonstrated ability.

AI

AI use is encouraged. I use AI extensively and want an assistant who knows how to use it well.
AI should improve your judgment and efficiency—not replace your judgment.

How to Apply

Apply with short numbered answers to the seven questions below. A resume or general cover letter alone does not complete the application.
Keep your answers concise. You may use AI, but if you do, tell me briefly how you used it.
Finalists will be invited to complete a paid practical exercise based on realistic work from this role.

Application Questionnaire

Apply through OnlineJobs.ph with numbered answers. No separate application form is required. Keep the entire response concise, approximately 400 words or fewer. AI assistance is welcome if disclosed.

1. Availability and rate

Confirm that 15–20 hours/week initially works for you. Give your exact Monday–Friday start and end times in Pacific Time, including at least two hours entirely within 9 AM–5 PM, and your requested hourly rate within the advertised range. Note any overlapping work commitments without naming clients. If your availability differs, say so plainly.

2. Relevant experience

Describe your most similar owner/executive support role and what you personally owned.

3. Ownership and pushback

Describe one actual i ---------- in 3–5 sentences: what commitment was at risk, what YOU personally did, and what happened. Use Situation / My action / Result. A small, specific example is better than general statements about being proactive. Anonymize private details; no work samples are needed.

4. Security judgment

An unexpected bank-reset email arrives in an inbox you help with. In two or three sentences, what do you do?

5. AI use

Give one useful AI example and how you checked the result. Disclose any AI used for this application.

6. Calls

Calls for scheduling, vendor coordination and follow-up are part of this role. Briefly describe one professional call you personally handled, its purpose and outcome, and whether you have called U.S. businesses. If your experience is written support only, say so; willingness to learn and prior experience are different.

7. Reliability and individual work

Describe your internet/power backup plan. Will you personally perform the work? Any proposed helper, agency involvement or subcontracting must be disclosed; account sharing or undisclosed substitutes are not permitted.
Do not submit identification documents, bank details, passwords, or a previous employer's confidential work.