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 company behind WordPress.com, Tumblr, Woo, and more.

You’re not just assisting. Wranglers are Matt’s force multipliers: a tight-knit, two-person team, soon to be three, who quarterback priorities, intercept chaos, and make the impossible look effortless. You’ll help Matt and Automattic move at lightspeed by smoothing logistics, triaging demands, and solving problems nobody else even sees.

This is a remote-first, global role. Work from anywhere with Wi-Fi, although candidates based in the West Coast US or APAC time zones are preferred to best support the team’s needs. The role may require irregular hours and collaboration across different time zones.

Automattic offers open vacation, parental leave, wellness support, sabbaticals, and true work-life flexibility. The salary range is $95,000–$195,000 USD annually, with compensation paid in local currency according to location.

Automattic is committed to diversity, equity, and inclusion. The company is fully remote, distributed globally, and welcomes applications regardless of location.

• Scrappy and resourceful, with experience supporting high-caliber executives in ambiguous, ever-changing organizations; startup, technology, and remote-environment experience is a plus.
• Radically humble, ego-free, unflappable, and comfortable working behind the scenes or at the center of the action.
• Demonstrates extreme ownership and is willing to handle any task, regardless of size.
• Ultra-reliable, with a strong record of following through on commitments.
• Curious and quick to learn, with an interest in using emerging technologies such as AI to improve team effectiveness.
• Comfortable collaborating globally, working irregular hours, and engaging with people from diverse backgrounds.
• Emotionally acute, with the ability to read situations, deliver sensitive news, recognize stress, and provide perspective.
• Not seeking a rigid structure, mandated task list, personal brand-building opportunity, or traditional career-ladder environment.

• Partner with Matt and the Wranglers team as a trusted, behind-the-scenes operator.
• Triage priorities, block distractions, and manage calendars, communications, last-minute travel, meetings, and project logistics.
• Anticipate needs, handle urgent issues, own unexpected situations, and exercise sound judgment under pressure and competing priorities.
• Interface professionally and discreetly with high-profile partners, board members, and executives worldwide.
• Conduct research and support meeting preparation and follow-up, filling gaps before they become visible.
• Identify inefficiencies and create better processes, including refining workflows, developing travel solutions, and organizing information systems.
• Support and challenge the team while contributing candor, humor, and practical day-to-day support.
• Provide support across different time zones as needed.