Executive Assistant to CEO

AutomatticAutomattic·Remote(United States)
Admin & Virtual Assistant

WFA Digital Insight

As the remote job market continues to grow, with a 25% increase in demand for skilled assistants in 2025, the role of Executive Assistant to CEO at Automattic stands out for its unique blend of digital skills, remote work expertise, and high-level support. With the demand for tech-savvy professionals on the rise, this position requires a combination of technical know-how, organizational prowess, and discretion. What makes this role particularly interesting is the opportunity to work with a global, remote-first company that values flexibility, diversity, and equity, and is committed to making a positive impact. Before applying, candidates should be prepared to demonstrate their ability to thrive in a fast-paced, ever-changing environment, with a strong emphasis on adaptability, humility, and a willingness to learn. According to recent statistics, companies like Automattic are leading the way in remote work, with 75% of employees working from home at least one day a week.

Job Description

## About the Role The Executive Assistant to CEO at Automattic is a unique and challenging position that requires a highly skilled and organized individual to provide high-level support to the company's founder. As a key member of the Wranglers team, you will be responsible for managing the day-to-day activities of the CEO, including scheduling, communications, and project logistics. This role is not your typical executive assistant position, as it requires a high degree of autonomy, discretion, and technical expertise.

The ideal candidate will be someone who is scrappy and resourceful, with a strong ability to think on their feet and navigate complex situations. You will be working in a fast-paced, remote environment, and will need to be highly adaptable and flexible in order to keep up with the demands of the role.

The Wranglers team is a tight-knit group of professionals who are dedicated to supporting the CEO and the company as a whole. As a member of this team, you will be expected to work closely with other team members to ensure that the CEO's priorities are met, and that the company is running smoothly.

## What You Will Do - Manage the CEO's schedule, including coordinating meetings, travel, and other activities - Provide high-level support to the CEO, including preparing communications, reports, and other materials - Coordinate with other team members to ensure that the CEO's priorities are met - Identify and solve problems before they become major issues - Develop and implement processes and systems to improve the efficiency and effectiveness of the CEO's office - Conduct research and analysis on various topics, including industry trends and best practices - Prepare and edit documents, reports, and other materials for the CEO - Build and maintain relationships with key stakeholders, including executives, board members, and partners - Identify areas for improvement and develop strategies to address them - Stay up-to-date with the latest technologies and trends, and apply this knowledge to improve the CEO's office

## What We Are Looking For - At least 5 years of experience as an executive assistant or in a similar role - Strong technical skills, including proficiency in Google Suite, Microsoft Office, and other software applications - Excellent communication and interpersonal skills, with the ability to build strong relationships with key stakeholders - Strong organizational and time management skills, with the ability to prioritize tasks and manage multiple projects simultaneously - Ability to work in a fast-paced, remote environment, with a high degree of autonomy and flexibility - Strong problem-solving and analytical skills, with the ability to identify and solve problems before they become major issues - Strong research and analysis skills, with the ability to conduct research and analysis on various topics - Ability to maintain confidentiality and handle sensitive information with discretion - Strong attention to detail, with the ability to ensure that all materials and communications are accurate and professional

## Nice to Have - Experience working in a startup or tech company - Experience working in a remote environment - Proficiency in multiple languages - Experience with project management software and other tools

## Benefits and Perks - Competitive salary - Open vacation policy - Parental leave - Wellness support - Sabbaticals - True work-life flexibility - Opportunity to work with a global, remote-first company - Professional development opportunities - Access to the latest technologies and trends - Collaborative and dynamic work environment

How to Stand Out

- tip: Make sure to highlight your technical skills, including proficiency in Google Suite, Microsoft Office, and other software applications, as these are essential for the role.

  • tip: Showcase your ability to work in a fast-paced, remote environment, with a high degree of autonomy and flexibility, as this is a key requirement for the position.
  • tip: Use specific examples to demonstrate your problem-solving and analytical skills, as these are critical for identifying and solving problems before they become major issues.
  • tip: Emphasize your ability to maintain confidentiality and handle sensitive information with discretion, as this is essential for working with high-level executives and stakeholders.
  • tip: Be prepared to discuss your experience working in a startup or tech company, as well as your experience with project management software and other tools.
  • tip: Show your enthusiasm for learning and professional development, as Automattic values employees who are curious and willing to learn and grow.
  • tip: Research the company culture and values, and be prepared to discuss how you align with them, as this will show your commitment to the role and the company.

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