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Executive Assistant to CEO job at Automattic in Work from Anywhere

July 20, 2026

Executive Assistant to CEO This isn’t your typical EA… Are you energized by chaos—yet quietly love bringing order to it? Do you spot what’s about to break before anyone else, and fix it—without being asked? Are you a behind-the-scenes operator who leaves your ego at the door, rolls up your sleeves, and finds reward in making others shine? If so, you might be the next Wrangler for Matt Mullenweg, founder of Automattic (the folks behind WordPress.com, Tumblr, Woo, and more). Wait, what’s a Wrangler? You’re not just assisting. Wranglers are Matt’s force multipliers: a tight-knit, two-person (soon three) team who quarterback priorities, intercept chaos, and make the impossible look effortless. You’ll help Matt—and Automattic—move at lightspeed, smoothing logistics, triaging demands, and solving problems nobody else even sees. What You’ll Really Do Partner with Matt and the Wranglers team as a trusted, behind-the-scenes operator. Triage priorities, block distractions, and quietly make things run seamlessly—calendars, communications, last-minute travel, meetings, and project logistics. Own the unexpected: anticipate needs, handle urgent issues, and exercise judgment under pressure and competing priorities. Interface with high-profile partners, board members, and execs worldwide—always with professionalism and discretion. Go deep on research, prep, and follow-up for meetings—filling gaps before anyone even notices they exist. Spot inefficiencies and invent better ways—whether refining workflows, improvizing travel hacks, or organizing information in a cleaner system. Support and challenge the team, offering and receiving candor, humor, and practical support daily. Who Thrives Here Scrappy and resourceful: You’ve supported high-caliber execs in ambiguous, ever-changing organizations (startups, tech, remote environments a plus). Radically humble: Ego-free, unflappable, and as happy in the background as you are at the center of the action. Extreme ownership: If it needs to be done, you do it—no matter how big or small. Ultra-reliable: Your word is gold; when you’re on it, it’s handled. Curious and quick: You have an insatiable appetite for learning—especially about how new technologies, such as AI, can enhance your team’s effectiveness. You experiment, tinker, and share new discoveries. Worldly: Comfortable collaborating globally, working irregular hours, and with people from diverse backgrounds. Emotionally acute: You read the room, deliver news sensitively, and can spot stress (and bring perspective) before it derails anyone. What This Isn’t Not for clock-punchers or ladder-climbers. Not a backstage pass to personal brand-building. Not for those seeking a rigid structure or a mandated task list. Location & Benefits Remote-first, global: Work from anywhere with Wi-Fi, but our ideal candidate is based in the West Coast US or APAC time zones to best support the team’s needs. Flexibility is key: sometimes random hours—Matt is always moving! World-class benefits: Open vacation, parental leave, wellness support, sabbaticals, and true work-life flexibility. We are currently prioritizing candidates who are willing to support across different time zones Automattic is committed to diversity, equity, and inclusion. We thrive on differences and welcome all applications, regardless of your location. Salary range: $95,000 – 195,000 USD. Please note that salary ranges are global, regardless of location, and we pay in local currency. We are searching for high-caliber candidates with the skills and qualities to have a net positive for Automattic. Pay will reflect the potential contribution and the impact you can bring, which may, in some cases, go beyond the range stated. We’re pleased to offer a straightforward, competitive base salary, providing financial clarity without complex variable components. This isn’t your typical work-from-home job: we are a fully-remote company with an open vacation policy.

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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...