Senior US Executive Assistant (WFH)

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 dynamic private family office led by a husband-and-wife team who operate across multiple professional and personal domains. With business interests rooted in innovation, strategic investment, and global operations, the principals are fast-paced, detail-oriented, and deeply value precision, discretion, and proactive support. Their work style blends high trust with high expectations—and they seek team members who match their drive and professionalism. While the principals are based in Miami, Florida, they frequently travel internationally and rely on a core remote team to keep operations running seamlessly behind the scenes.

About the Role

This is a high-trust, high-impact Senior US Executive Assistant position supporting both principals in their professional and personal affairs. The ideal candidate is an independent problem solver, comfortable navigating ambiguity and juggling priorities with a calm, confident, and proactive approach. You’ll play a key role in keeping operations running smoothly—whether it’s managing schedules, coordinating household vendors, preparing concise updates, or simply anticipating needs before they arise.

This role is fully remote and designed for someone who thrives in fast-moving environments, is tech-savvy (especially with tools like ChatGPT, Notion, and Google/Microsoft Suites), and is eager to become a reliable, long-term extension of the client's team.

What you’ll do

• Manage complex calendars, appointments, and meeting logistics (both personal and professional).

• Track and drive completion of key tasks and projects with minimal follow-up.

• Prepare briefings, updates, and summaries in a clear, structured format.

• Conduct vendor/product/travel research with thoroughness and attention to detail.

• Handle expense reports, budget tracking, and simple spreadsheet management.

• Coordinate household vendors and service providers (housekeeping, landscaping, pool, IT, etc.).

• Troubleshoot basic tech issues across Mac/PC/iOS platforms.

• Ensure consistent support even while principals are traveling—managing time zones, communications, and light coordination as needed.

Requirements

What You Bring

• Minimum 5 years of experience as an Executive Assistant, ideally in a remote or fast-paced setup.

• Excellent written and verbal English communication; Spanish or additional languages are a strong plus.

• Highly organized, detail-oriented, and capable of managing multiple workstreams simultaneously.

• Proficient with Microsoft Office 365, Google Workspace, and modern productivity tools (e.g., Notion, ChatGPT).

• Strong numeracy, research, and summarization skills.

• High-speed internet and a professional remote setup.

• Flexible with time zones, with occasional availability to align with Eastern Time (Miami).

• Ability to pass a background check.

• Willingness to occasionally travel or collaborate in-person, if required.
  

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.