Senior Executive Assistant to CEO

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TYPE OF WORK

Full Time

SALARY

$1,200–$1,700 / month

HOURS PER WEEK

40

DATE UPDATED

Apr 8, 2026

JOB OVERVIEW

Senior Executive Assistant

Full-Time | Remote — Philippines-Based | Microsoft Outlook + AI Tools Required


About You ------------------------

You thrive in complexity. You don't just manage calendars — you manage entire worlds. You've supported a senior executive before, and you understand that your job is to make their life run so smoothly that they barely notice the logistics.

You're already a power user of Microsoft Outlook and know how to build a system, not just respond to one. You're genuinely excited about AI — you use LLMs regularly in your own workflow and you see them as a force multiplier, not a novelty.

You think three steps ahead. You read an email and immediately understand what it means for the week. You see a gap in the calendar and know it needs to be filled. You anticipate, you prepare, and you follow through — without being asked twice.

If you're looking for a high-trust, full-time role where you'll be genuinely indispensable to a dynamic CEO running multiple businesses, a nonprofit, a real estate portfolio, and a rich family life — this is the role.


About Performance Excellence Partners ------------------------

Performance Excellence Partners (PEP) is a multimillion-dollar, woman-owned government contracting agency with a 26-year track record of executing complex federal contracts. Led by CEO Rachel Ramirez, PEP is built on a culture of uncommon integrity, inspired problem-solving, and lasting impact.

Rachel also leads a growing coaching and leadership development practice (Pinnacle and PEP Coaching), serves on multiple boards, manages a portfolio of real estate properties, and founded RMLA — a nonprofit focused on community leadership. She is, in short, someone who operates at the highest level in every domain of her life — and needs an EA who can match that pace.


About the Role ------------------------

This is a full-time, remote position based in the Philippines. You will work directly with Rachel as her primary EA, serving as the operational backbone of her professional and personal life.

You'll own her Outlook — email, calendar, contacts, and communications. You'll coordinate her boards, her nonprofit, her travel, her family's logistics, and her properties. You'll turn her coaching ideas into polished content. And you'll always be one step ahead of what she needs next.

Morgan, Rachel's current assistant, will train you on all systems and processes. This is a long-term relationship built on trust, and we're looking for someone who intends to grow into it.


What You'll Do ------------------------

Calendar & Communications

Own the CEO’s Outlook — build and maintain folder structure, rules, and filters for all categories
Manage the CEO’s calendars across PEP, coaching, nonprofit, and personal/family — with full supporting context in every meeting notice
Manage the VP’s calendars for PEP and family as secondary responsibility
Draft, send, and manage professional email correspondence on Rachel's behalf
Confirm attendance, RSVPs, and registrations for boards, events, and community activities

Nonprofit, Board & Project Management

Own nonprofit operations: monthly speaker coordination, agendas, confirmations, happy hours, community projects, website updates, newsletter
Track commitments across all boards
Manage certification processes — applications, renewals, monthly reports, activity logs
Track badge renewals, credentials, and compliance deadlines in a master tracker
Assist with active loan documentation for airport clients

Travel, Logistics & Admin

Research, book, and build complete itineraries for all business and personal travel
Prepare expense reports and organize receipts for bookkeeper review
Review and prepare travel reimbursements and consultant invoices for payment
Cross-check PEO payroll output for accuracy against timesheet records
Order supplies, manage vendor relationships, schedule and coordinate deliveries

Properties & Personal Life

Monitor Buildium for maintenance issues, tenant activity, and lease expirations
Coordinate property maintenance vendors and contractors
Manage international property logistics (Mexico: visa, Airbnb revenue tracking, utilities)
Handle family logistics: appointments, car registrations, children's volunteer hours, college prep
Support father-in-law care coordination as needed

Content & Social Media

Support CEO’s LinkedIn presence: share content, respond to comments, connect with key contacts
Manage PEP MailChimp and send e-blasts on schedule
Turn CEO's ideas, notes, and church reflections into formatted PowerPoint slides and coaching content
Assist with light website updates for RMLA and PEP

A Day in the Life

You start your morning (overlapping with Rachel's early Pacific Time hours) by scanning her Outlook. You see three new board emails and a travel confirmation that needs a hotel added. You handle both before she's had her coffee.

You check the RMLA speaker confirmation list — two of next month's speakers haven't responded. You send a follow-up, update the tracker, and draft the agenda for Wednesday's session.

A Buildium alert comes in for the Huntington Beach property — a tenant maintenance request. You log it, contact the plumber Rachel uses, and confirm the appointment. You make a note in the property tracker.

In the afternoon you turn Rachel's voice memo from Sunday's church message into a structured PowerPoint outline she can review and use for her next coaching session. You end the day with her calendar fully prepped for the week ahead and her inbox organized.


What We're Looking For ------------------------

Minimum 4 years of executive assistant or chief-of-staff-level support experience
Demonstrated experience supporting a senior executive across both professional and personal domains
Microsoft Outlook power user — rules, folders, calendar management, contact systems (required)
Genuine proficiency with AI/LLM tools (Claude, ChatGPT, or equivalent) — used regularly, not experimentally
Experience with nonprofit coordination, board support, or community organization management
Property management platform experience (Buildium or similar) a significant advantage
Strong content creation and PowerPoint skills — can turn ideas into polished presentations
Excellent written and spoken English — professional, confident, and clear
Bachelor's degree preferred; advanced degree a differentiator
Long-term mindset — looking for a career relationship, not a contract


Schedule & Compensation ------------------------

Full-time, approximately 40 hours per week
Daily overlap with U.S. Pacific Time required (2–4 hours minimum, morning preferred)
Compensation: $7–$10 USD/hour based on experience — top-tier for the market
Paid monthly via direct bank transfer
Long-term engagement with strong growth potential as trust and scope expand

We invest in the right people. If you're exceptional, you'll be compensated and treated like it.


How to Apply ------------------------

Please submit your application here:

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Thank you for taking the time to help us get to know you.

SKILL REQUIREMENT
Calendar Management Email Management Executive Assistance
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