Executive Assistant + HR Manager (Philippines) — Confidential Search, Long-Term Role

About This Role

This is a confidential search. We are an established US-owned company with an existing Philippines-based
remote team, and we have been named a Great Place to Work in the past. We are not naming the company in
this posting. Shortlisted candidates will be told exactly who we are before any
interview, and we will answer every question you have about the business at that stage.

We need one person wearing two hats: half the week supporting our owners and senior leaders as
an Executive Assistant, and half the week running HR operations for our Philippines team.

Neither half is a full-time job on its own. Together, they are. That is the honest shape of this
role — and it is why we need someone senior enough to switch between the two without dropping
either one.

You must have real, demonstrable experience in BOTH areas. Applications with only EA experience
or only HR experience will not be considered.

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Hat #1 — Executive Assistant (roughly 50%)

Supporting 1–2 executives:

- Calendar and meeting management
- Inbox triage, follow-ups, and prioritization
- Preparing summaries, documents, agendas, and internal reports
- Tracking commitments across the leadership team and chasing them to done
- Coordinating across teams and time zones
- Using tools, systems, and AI to give the executives their time back
- Thinking one step ahead — finding the task before it is assigned to you

Hat #2 — HR Manager (roughly 50%)

Running people operations for our Philippines-based team:

- Payroll coordination, payroll filings, and payment processing
- Maxicare enrollment, payments, and day-to-day administration
- HR documentation and personnel records
- Compliance with Philippine labor rules and best practice
- Hiring support, onboarding, and offboarding
- Serving as the HR point of contact for team members
- Tracking attendance and time, and surfacing issues early
- Protecting and building on a culture we have already been recognized for

This role sees confidential information — compensation, performance, personal records.
Discretion is not a nice-to-have. It is the job.

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Attendance and Availability — Read This Carefully

We are direct about this because it matters more to us than any other single line in this post.

- This role works US business hours.
- This role must be reliably online and reachable during those hours. Executives and team
members depend on you being there.
- If you cannot commit to a consistent, predictable schedule, please do not apply.
- Time off is expected and supported. Unplanned absences without notice are not.
- We will ask about your attendance record in prior roles, and we will ask your references about
it specifically.

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Required Experience (all of these)

- Prior experience as an Executive Assistant supporting senior leaders or owners. Proven success supporting executives with proactive processes is very important to us.
- Prior experience as an HR Manager or HR Lead in the Philippines. You will be an advocate for the culture so we need someone who can exhibit our culture with the team and build strong relationships internally.
- Working knowledge of PH labor rules, payroll, statutory filings, and benefits administration
- Hands-on experience with Maxicare or a comparable HMO — enrollment, billing, member issues
- Excellent written and spoken English
- High discretion and professionalism with confidential information
- Able to work independently, set your own priorities, and follow through without being chased
- Reliable internet, a working backup connection, and a quiet place to work
- Curiosity about AI and technology, and a track record of using it to work faster

Expectations

- Experience supporting founders, owners, or C-level executives
- Experience with remote teams or call center / BPO environments
- Familiarity with AI and automation tools
- A record of improving systems and processes, not just running them
- Culture-building or employee-engagement experience

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What You Get

- A seat at a company named a Great Place to Work — this is a culture people stay in, and you
will be one of the people responsible for keeping it that way
- Long-term, stable role — we are hiring for years, not months
- Direct access to company ownership and senior leadership
- Real ownership of HR for the Philippines team
- Exposure across the whole business — this is a growth seat for the right person
- Remote, Philippines-based
- Standard benefits for the role
- Compensation is based on experience. We pay well for the right person, and we will discuss
numbers openly once we know what you bring. Tell us your expected monthly rate in your
application.

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How to Apply — Follow Every Step

We screen on attention to detail first. Any application missing a step below will not be reviewed.

1. Start your cover letter with the exact phrase: Two Hats
2. A short cover letter covering your EA experience and your HR experience separately, and the
concrete value you delivered in each
3. Your resume
4. Three specific examples of how you made an executive more efficient or improved an HR
operation — with the actual result, not a description of the duty
5. The tools you have used: HR, payroll, HMO portals, productivity, AI
6. How you have used AI tools in a prior role — be specific about the task and the outcome
7. Your current availability, the hours you can work, and the date you could start
8. Your expected monthly rate
9. Optional but appreciated: a short video introduction

If you are detail-focused, curious, proactive, and you want a seat where your work is visible to
the people who run the company — follow the steps above exactly and send it in. Please do not submit an application if you don't meet the experience requirements or cannot provide the requested information.

Thank you! We look forward to meeting the right person for this next career step.