Senior Executive Assistant (Remote - US Shift)

About Penbrothers

Penbrothers is an HR & remote talent management partner and one of the fastest growing companies in the Philippines. We provide talented Filipinos with global opportunities in high-growth startups and dynamic companies, from the comfort of their own homes.

About The Client

Our client is a multi-company founder and CEO with a passion for building innovative businesses and making a positive impact. With a background in the military and construction trades, he has a proven history of success, having led firms recognized in the Inc. 5000 and the Los Angeles Business Journal’s "Top 100 Fastest Growing" list.

He leads a diverse portfolio of ventures, including a premier project management firm, a general contractor specializing in revitalizing iconic buildings, a real estate development company leveraging new technology, a business collective for launching ventures, and a non-profit focused on children's books. This role is a unique opportunity to partner with a dynamic leader who is not only an accomplished entrepreneur but also an avid investor and philanthropist.

About The Role

We are seeking a Senior Executive Assistant to serve as the strategic right hand to a multi-company founder and CEO. This is not a traditional assistant role — you will act as the CEO’s Second Brain, orchestrating priorities, managing execution, and ensuring nothing falls through the cracks across multiple businesses, personal commitments, and creative ventures.

You’ll combine detail-obsessed organization, proactive follow-through, and operational thinking with the ability to leverage AI tools (especially ChatGPT) to streamline workflows. This role requires someone who can manage day-to-day execution, anticipate needs, and create clarity from complexity — allowing the CEO to focus on vision, strategy, and relationships.

What You’Ll Do

• Weekly Operating System

• Email, Calendar & Commitments

• Communication & Follow-Up

• Podcast & Media Support
• Personal & Travel Logistics
• Own the planning and reporting rhythm for the CEO’s life and businesses.
• Deliver the Friday Executive Report, covering: upcoming meetings, top priorities, tactical tasks, people follow-ups, and completed vs. slipped tasks with recommendations.
• Provide monthly analysis on trends, recurring friction points, and process improvements.
• Capture and systematize key information from inboxes, notes, and Microsoft Suite tools.
• Manage and review up to 70% of the CEO’s emails, handling follow-ups and flagging priorities.
• Maintain a conflict-free calendar, protect deep work and family time, and anticipate prep needs for meetings.
• Track deadlines and ensure delivery through proactive reminders and follow-ups.
• Manage People Follow-Ups to ensure no opportunity or task is lost.
• Draft and send professional communications, with growing independence (starting at 25% and scaling to 75%).
• Confidently interact with senior executives, partners, and stakeholders.
• AI & Productivity Enablement
• Use ChatGPT and other AI tools to draft content, analyze reports, handle routine emails, and generate first drafts of decks, proposals, and research.
• Continuously introduce AI-driven solutions to increase efficiency and compress work hours.
• Support podcast production, scheduling, guest prep, and post-production coordination.
• Assist with media, content, and thought leadership initiatives.
• Research, plan, and book travel, events, and family commitments.
• Maintain a structured, organized file system in OneNote and OneDrive.

Requirements

What You Bring

• At least 5+ years of experience in executive operations, Senior Executive Assistant (EA), project coordination, or operations roles supporting C-level executives.
• Strong organizational and follow-through skills — nothing slips through the cracks.
• Exceptional written and verbal communication in English.
• Proactive, detail-oriented personality with a strong sense of accountability.
• Proven ability to manage multiple priorities across business and personal domains.
• High intelligence, curiosity, and ability to learn quickly.
• Proficiency in Microsoft Suite (Outlook, OneNote, OneDrive, Excel, PowerPoint).
• Comfort leveraging AI tools (especially ChatGPT) for productivity.
• Independent, remote-ready work style with discipline and ownership.

• What Winning Looks Like:

• Why This Role Is Unique:

• The CEO enters each week with clarity on top priorities, meetings, and follow-ups.
• No deadlines missed, no opportunities lost.
• Emails, commitments, and files are organized and proactively managed.
• Weekly reports and systems keep execution on track.
• The CEO’s time is protected — allowing focus on strategy, growth, and relationships.
• You grow into a trusted execution partner, taking on more decision-making and operational responsibility.
• You will be plugged into multiple ventures: construction, real estate, AI hedge funds, disaster recovery, future tech, and media projects.
• This role blends traditional EA responsibilities with operations, project management, and AI-driven productivity.
• Exceptional performance leads to expanded trust, influence, and growth opportunities.

Hiring Process

We utilize AI tools to enhance our hiring efficiency and ensure a fair evaluation of all candidates. As a result, candidates who passed our initial evaluations should expect an AI Interviewer as a component of our recruitment process. This is supervised by Human Talent Acquisition Experts who will also engage with you throughout your application journey.

What You’Ll Get

At Penbrothers, we are obsessed with creating positive employee experiences. Here you’ll find an environment that nurtures learning and provides opportunities for growth. You’ll have the opportunity to make an impact on fast-growing startups and dynamic companies. 

• Meaningful work & Growth: We take every opportunity to stretch ourselves and deliver an excellent client experience.
• Employee as our biggest asset: We are genuinely invested in our people’s career and welfare.
• Global reach & local impact: Get to work with high-growth startups and dynamic companies from the comfort of your own home.
• Powering global startups: We’ve created 1,400 Filipino jobs that empower global start-ups to focus on growth.