Executive Assistant to CEO

September 14, 2026

Other Jobs To Apply

No other job posts for this day.

Automattic is seeking an Executive Assistant to the CEO, Matt Mullenweg, a role they refer to as a "Wrangler." This isn't a typical EA position; it's for someone who thrives on bringing order to chaos, anticipates needs, and proactively solves problems before they escalate. The ideal candidate will act as a force multiplier, enabling the CEO and the company to operate at lightspeed. The Wrangler team is a small, tight-knit group responsible for quarterbacking priorities, intercepting distractions, and ensuring seamless operations. This involves managing calendars, communications, travel, meetings, and project logistics. The role requires a behind-the-scenes operator who is ego-free, highly resourceful, and committed to making others shine, particularly in a fast-paced, remote-first environment. This position is not for those seeking a rigid structure or a mandated task list, nor is it for clock-punchers or personal brand-builders. It demands extreme ownership, ultra-reliability, and a curious mind, especially regarding how new technologies like AI can enhance team effectiveness. The company emphasizes a global, remote-first culture with world-class benefits and a commitment to diversity.

Requirements

Supported high-caliber executives in ambiguous, ever-changing organizations (startups, tech, remote environments a plus). Radically humble, unflappable, and comfortable in a supporting role. Demonstrates extreme ownership; if it needs to be done, you do it. Ultra-reliable; your word is gold and tasks are handled. Curious and quick learner, especially regarding new technologies like AI. Comfortable collaborating globally and working irregular hours. Emotionally acute; able to read the room, deliver news sensitively, and offer perspective.

Responsibilities

Partner with Matt Mullenweg and the Wranglers team as a trusted, behind-the-scenes operator. Triage priorities, block distractions, and ensure seamless operations for calendars, communications, travel, meetings, and project logistics. Anticipate needs, handle urgent issues, and exercise judgment under pressure and competing priorities. Interface with high-profile partners, board members, and executives worldwide with professionalism and discretion. Conduct deep research, prep, and follow-up for meetings, filling gaps proactively. Identify inefficiencies and invent better ways, refining workflows, improvising travel hacks, or organizing information. Support and challenge the team, offering and receiving candor, humor, and practical support daily.

Back to blog

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...