New

Executive Assistant to CEO

Remote

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 or works comfortably with 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 in the PST timezone. (UTC-8)

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. To see a full list of benefits by country, consult our Benefits Page. And check out these links to learn more about How We Hire and What We Expect from Ourselves. #LI-DNI

About Automattic 

Now in our 20th year, we’re the people behind WordPress.com, WooCommerce, Tumblr, Simplenote, Jetpack, Longreads, Day One, PocketCasts, Beeper, and more. We believe in making the web a better place.

We’re a distributed company with more than 1400 Automatticians in nearly every corner of the globe, speaking over a hundred different languages. Enriched by this diversity, we’re united by a singular mission: to democratize publishing, commerce, and messaging so anyone with a story can tell it, anyone with a product can sell it, and everyone can manage their communications from a single source. In short, we help maintain a balance in society, creating and continually refining powerful tools people can use to compete fairly—regardless of income, gender, politics, language, or where they live in the world.

We believe in Open Source, and the vast majority of our work is available under the GPL. Automattic is a Most Loved Company and Disability Confident Committed. (Here’s what that might mean for you.) Learn more about our dedication to diversity, equity, and inclusion and our Employee Resource Groups.

If you need disability-related accommodations during the application or interview process, please fill out this form. We are committed to ensuring an accessible hiring process for all candidates. 

To learn about how we handle your data, please review our Privacy Policy.

You can track your application status and more at MyGreenhouse. 

All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, disability, or status as a protected veteran.

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