Executive Assistant (Remote) – Automattic

Job Description

Location: Remote (Global)
Employment Type: Full-Time
Salary: USD $95,000 – $195,000 per annum (paid in local currency)

About Automattic

Automattic is the company behind some of the world’s most widely used internet platforms, including WordPress.com, WooCommerce, Tumblr, Jetpack, Pocket Casts, Simplenote, Day One, Beeper, and several other products that empower millions of people to publish, communicate, and do business online.

With more than 1,500 employees working remotely across the globe, Automattic is committed to building an open web where anyone, regardless of location or background, can create, share, and grow online. The company operates as a fully distributed organization, embracing flexibility, innovation, collaboration, and continuous learning.

Automattic is currently seeking an exceptional Wrangler (Executive Operations Partner) to support its Founder, Matt Mullenweg, by providing world-class executive, operational, and strategic support within a highly dynamic global environment.

About the Role

This is far more than a traditional Executive Assistant position.

As a Wrangler, you will become part of a small, high-performing operations team responsible for helping one of the technology industry’s leading entrepreneurs operate at maximum effectiveness. Acting as a trusted strategic partner behind the scenes, you will anticipate challenges before they arise, coordinate complex priorities, remove obstacles, and create the operational clarity that enables leadership to focus on the company’s most important objectives.

The role requires exceptional judgment, emotional intelligence, adaptability, and the ability to remain calm while managing constantly changing priorities. You’ll thrive if you enjoy solving complex problems, operating independently, and finding satisfaction in making others successful.

This fully remote position is ideal for professionals who excel in ambiguity, embrace ownership, and consistently deliver excellence with minimal supervision.

Key Responsibilities

As the Wrangler, you will:

• Serve as a trusted operational partner to the Founder and the Wrangler team.
• Manage complex executive calendars, schedules, meetings, and competing priorities across multiple international time zones.
• Anticipate operational challenges and proactively resolve issues before they impact business activities.
• Coordinate domestic and international travel, including last-minute itinerary changes and logistical planning.
• Prepare comprehensive briefing materials, research, meeting agendas, and follow-up actions for executive meetings.
• Screen, prioritize, and coordinate executive communications while ensuring timely responses and appropriate follow-up.
• Build and maintain professional relationships with senior executives, board members, business partners, and key stakeholders worldwide.
• Identify operational inefficiencies and implement improved systems, workflows, and administrative processes.
• Coordinate special projects while managing multiple high-priority initiatives simultaneously.
• Exercise sound judgment when handling confidential and highly sensitive information.
• Support cross-functional collaboration by ensuring seamless communication between leadership and internal teams.
• Leverage technology, automation, and AI tools to improve productivity, streamline operations, and enhance team effectiveness.
• Provide calm, thoughtful support during rapidly changing situations while maintaining professionalism and discretion.

Qualifications & Experience

The successful candidate should possess:

• Proven experience supporting senior executives, founders, or C-suite leaders in a fast-paced business environment.
• Previous experience as an Executive Assistant, Chief of Staff, Executive Operations Partner, or similar strategic administrative role.
• Exceptional organizational and time management skills with the ability to manage multiple priorities simultaneously.
• Strong decision-making abilities and excellent professional judgment.
• Outstanding written and verbal communication skills.
• High emotional intelligence with the ability to build strong professional relationships across diverse teams and cultures.
• Experience working in remote, distributed, startup, or technology-focused organizations is highly desirable.
• Strong research, planning, and project coordination capabilities.
• Demonstrated ability to solve problems independently and proactively.
• Absolute discretion when handling confidential information.
• Curiosity and enthusiasm for learning new technologies, including AI-powered productivity tools.
• Flexibility to collaborate across multiple global time zones and accommodate changing schedules when necessary.

Key Competencies

The ideal candidate will demonstrate:

• Strategic thinking
• Operational excellence
• Exceptional attention to detail
• Proactive problem-solving
• Emotional intelligence
• Adaptability and resilience
• Strong ownership mindset
• Integrity and reliability
• Professional discretion
• Collaboration and teamwork
• Innovation and continuous improvement
• Excellent interpersonal skills

Why Join Automattic?

Automattic offers an opportunity to work alongside some of the world’s most talented professionals while helping shape products used by millions globally.

Employees enjoy:

• Competitive annual salary of USD $95,000 – $195,000
• Fully remote work from anywhere with a reliable internet connection
• Flexible working arrangements with location independence
• Open vacation policy
• Paid parental leave
• Wellness and mental health support
• Sabbatical opportunities
• Comprehensive country-specific employee benefits
• Continuous professional learning and development
• Inclusive, collaborative, and globally diverse work environment
• Opportunity to work directly with one of the technology industry’s most influential founders

Who Will Thrive in This Role?

This opportunity is best suited for professionals who:

• Enjoy solving complex operational challenges.
• Take initiative without waiting for direction.
• Remain calm under pressure and adapt quickly to changing priorities.
• Prefer working behind the scenes to enable others’ success.
• Have a strong sense of ownership and accountability.
• Are naturally curious and continuously seek better ways of working.
• Value collaboration, humility, and continuous improvement.

How to Apply

Interested and qualified candidates are encouraged to apply through Automattic’s official careers portal.

When preparing your application, ensure your CV clearly highlights:

• Your experience supporting senior executives or founders.
• Executive operations, calendar management, and project coordination experience.
• Examples of managing complex priorities in fast-paced environments.
• Experience working remotely across international teams.
• Process improvement, workflow optimization, and operational leadership achievements.
• Experience using productivity, collaboration, automation, or AI tools to improve efficiency.

Your cover letter should demonstrate your ability to operate with discretion, exercise sound judgment, solve problems proactively, and support senior leadership in highly dynamic environments. It should also explain why you are excited about joining Automattic and contributing to its mission of making the web a better place.

Applications are reviewed on a rolling basis. Early applications are strongly encouraged.