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Executive Assistant (100% Remote, Tech Industry)

March 12, 2026

This a Full Remote job, the offer is available from: United States

Boldly is actively hiring a career executive assistant who is looking to provide long-term support, as an employee of Boldly, for senior leaders in the tech industry.

Boldly is 100% remote and has been since day one. Remote work isn’t just a perk for us, it’s how we operate. This role requires someone who is dynamic, professional, caring, and ridiculously talented at providing top notch support to senior leaders.

About the position

As an executive assistant and employee of Boldly, you will play the pivotal role of providing top-notch administrative support to senior-level executives in established Fortune 500 companies. Your work will be 100% remote and flexible during business hours, with no night or weekend work.

As an executive assistant, you’ll apply your professional skills in a wide range of tasks, including:

Strategically managing complex calendars for executives
Planning and scheduling meetings, conferences, and travel
Making travel arrangements including flight and hotel bookings
Maximizing the executive’s time by reading, researching, and routing correspondence; drafting letters and documents; collecting and analyzing information; initiating phone calls on their behalf
Managing multiple email inboxes for executives
Managing expenses
Providing customer/supplier support
Other executive admin responsibilities as needed

About you

You have at least 7 years of experience serving in a senior administrative support position where you provided support as an executive assistant working in a fast-paced environment supporting multiple high-level executives. At this point in your career, your #1 priority is to join a fully remote company that prioritizes flexibility in the workplace and promotes a culture of respect, kindness, and transparency. You are a team player with excellent communication skills and a positive outlook who cares deeply about helping others succeed. You know how and when to leverage technology to achieve goals, balanced with bringing a personal, human touch to your work. You take great pride in the quality of your work; you are proactive, dynamic, flexible, tech-savvy, results-oriented, and a stickler for details! And you do it all with a smile!

Required Skills and Experience:

A minimum of 7 years of direct hands-on experience as an executive assistant or senior administrative assistant to one or more executives (general admin experience as part of another role will not qualify)
Advanced knowledge of online software such as Google Workspace, Office 365, Zoom, and other popular productivity tools
Ability to multitask with ease and prioritize work as needed
Highly organized with excellent time management skills
Ability to learn new tools quickly
Excellent interpersonal communication
Strong writing skills
Ability to work independently and under the pressure of deadlines
Solution driven!

Benefits you’ll love, for full-time employees:

W2 employment status
Medical, dental, vision, and life insurance, with 100% of the premium paid by Boldly
401k with employer match
Paid time off including vacation/sick leave
Paid holidays
Paid parental leave
Technology stipend
Ongoing mentoring and support from your Boldly Team Leader to help you succeed with clients

Compensation

The pay range for this position is $27-$31 per hour, with starting pay based on location. Specific starting rates for full-time are as follows:

California & New York: $29 per hour
Washington, New Jersey, Colorado, & Massachusetts: $28 per hour
All other locations: $27 per hour

About our culture

We believe that it is possible to have a rewarding career that doesn’t conflict with your personal responsibilities and life choices. Our diverse team of executive assistants includes parents, military spouses, caregivers, and those with unique life situations where working remotely, part-time or full-time, and on a flexible schedule is not just a ‘nice to have’. Fostering a thriving company culture where everyone has a sense of belonging and enjoys coming to work is our # 1 priority. As a woman-owned business, we are intimately familiar with the challenges women and minorities face in the workplace and we are committed to maintaining a diverse, equitable, and inclusive workplace for all. And of course, as a remote-first company since our inception in 2012, we are longtime established experts at leading and succeeding in a remote work environment!

As a premium executive assistant company, we set the standard for remote professionals. We’ve been proudly certified as a Great Place to Work for 5 years in a row, and our accolades include being named by Fortune Magazine as one of the “50 Best Small Workplaces”, and Entrepreneur Magazine in their Entrepreneur 360 List as one of the “Best Entrepreneurial Companies in America” and by Color Magazine as a top Inclusive Workplace. Military Friendly named us as part of the Top 10 Military Spouse Friendly Employers, and FlexJobs as a Top 100 Company to watch for. We are also accredited by Flexa as a truly flexible employer.

Boldly hires ridiculously talented executive assistants for both full time and part time roles supporting our clients. Learn more on our website -

This offer from "Boldly" has been enriched by Jobgether.com and got a 79% flex score.

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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...