AI- forward Executive Assistant to the Co-Founder CEO - Remote

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AI-Forward Executive Assistant to the Co-Founder & CEO (Remote and can travel to Palo Alto, couple of times a month)

Overview
Join a profitable, fast-growing, AI-forward 130-person company headquartered in Palo Alto, California. This is a high-impact, high-trust role supporting the Co-Founder & CEO, with exposure to senior leadership, board members, investors, and global stakeholders.

You'll begin with full-scope executive support, then evolve the role by integrating AI tools and automation-building a scalable "human + machine" executive office.

Key Responsibilities

  • Executive Support (Primary)
    • Manage complex calendar, inbox, and priorities for the CEO
    • Coordinate internal and external meetings across multiple time zones
    • Prepare briefings, agendas, and follow-ups
  • Stakeholder Coordination
    • Interface with executives, board members, investors, partners, and government stakeholders
    • Maintain professionalism and confidentiality in high-trust interactions
  • Operational Excellence
    • Handle travel planning, expense management, and logistics
    • Track action items and ensure timely execution
  • Secondary Support
    • Provide scheduling, travel, and expense support to:
      • A second co-founder (subsidiary CEO)
      • Chief Revenue Officer (CRO)
  • AI & Automation (Core to Role Growth)
    • Start with manual workflows to build deep context
    • Introduce secure AI tools to streamline repetitive tasks
    • Design and manage agentic workflows to scale executive operations

Qualifications
  • 5+ years of experience as an Executive Assistant (supporting senior executives)
  • Proven ability to manage complex schedules across global time zones
  • Strong written and verbal communication skills
  • High level of discretion, judgment, and reliability
  • Experience with travel coordination, expense management, and executive operations
  • Comfortable working in fast-paced, high-growth environments

Preferred
  • Experience supporting founders or C-level executives
  • Exposure to AI tools, automation, or workflow optimization
  • Background in tech, SaaS, or defense-adjacent industries

Working Hours & Location
  • Fully remote
  • Primarily aligned with U.S. East Coast hours
  • CEO operates across U.S., EMEA, and APAC time zones; flexibility required

Why This Role
  • Direct partnership with a founder/CEO
  • Opportunity to build cutting-edge AI-enabled executive operations
  • High visibility and potential for role expansion as impact grows
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Common Interview Questions And Answers

1. HOW DO YOU PLAN YOUR DAY?

This is what this question poses: When do you focus and start working seriously? What are the hours you work optimally? Are you a night owl? A morning bird? Remote teams can be made up of people working on different shifts and around the world, so you won't necessarily be stuck in the 9-5 schedule if it's not for you...

2. HOW DO YOU USE THE DIFFERENT COMMUNICATION TOOLS IN DIFFERENT SITUATIONS?

When you're working on a remote team, there's no way to chat in the hallway between meetings or catch up on the latest project during an office carpool. Therefore, virtual communication will be absolutely essential to get your work done...

3. WHAT IS "WORKING REMOTE" REALLY FOR YOU?

Many people want to work remotely because of the flexibility it allows. You can work anywhere and at any time of the day...

4. WHAT DO YOU NEED IN YOUR PHYSICAL WORKSPACE TO SUCCEED IN YOUR WORK?

With this question, companies are looking to see what equipment they may need to provide you with and to verify how aware you are of what remote working could mean for you physically and logistically...

5. HOW DO YOU PROCESS INFORMATION?

Several years ago, I was working in a team to plan a big event. My supervisor made us all work as a team before the big day. One of our activities has been to find out how each of us processes information...

6. HOW DO YOU MANAGE THE CALENDAR AND THE PROGRAM? WHICH APPLICATIONS / SYSTEM DO YOU USE?

Or you may receive even more specific questions, such as: What's on your calendar? Do you plan blocks of time to do certain types of work? Do you have an open calendar that everyone can see?...

7. HOW DO YOU ORGANIZE FILES, LINKS, AND TABS ON YOUR COMPUTER?

Just like your schedule, how you track files and other information is very important. After all, everything is digital!...

8. HOW TO PRIORITIZE WORK?

The day I watched Marie Forleo's film separating the important from the urgent, my life changed. Not all remote jobs start fast, but most of them are...

9. HOW DO YOU PREPARE FOR A MEETING AND PREPARE A MEETING? WHAT DO YOU SEE HAPPENING DURING THE MEETING?

Just as communication is essential when working remotely, so is organization. Because you won't have those opportunities in the elevator or a casual conversation in the lunchroom, you should take advantage of the little time you have in a video or phone conference...

10. HOW DO YOU USE TECHNOLOGY ON A DAILY BASIS, IN YOUR WORK AND FOR YOUR PLEASURE?

This is a great question because it shows your comfort level with technology, which is very important for a remote worker because you will be working with technology over time...

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