Executive Assistant

The Executive Assistant at Tailscale is primarily tasked with supporting the SVP of Operations by managing calendars, facilitating meetings, and maintaining organization in various tasks. You will collaborate with the leadership team, prioritize requests, handle sensitive information, and assist in creating documents and presentations that drive initiatives.

To apply for the Executive Assistant position at Tailscale, candidates should have previous experience providing administrative support in a fast-paced, high-growth startup environment. Skills in organization, time management, communication, and attention to detail are essential. Proficiency with tools like Google Workspace could also be beneficial.

Tailscale offers a flexible, fully remote work environment that promotes work-life balance. As an Executive Assistant, you’ll collaborate with a globally distributed team, engage in virtual and in-person social events, and be part of a supportive and inclusive culture that values diversity.

Tailscale prioritizes professional development for its employees, including Executive Assistants. Each employee receives an annual budget for professional growth, access to mentorship programs, and opportunities for internal promotions to help you further your career.

Tailscale offers a competitive compensation package that includes health benefits, flexible paid time off, a home office setup budget, and a generous parental leave program. The company culture supports authenticity and provides opportunities for collaboration and personal growth.

In your response, highlight specific roles where you've supported executives, detailing the challenges you faced and how you overcame them. Emphasize your organizational skills, ability to prioritize tasks, and your proactive approach to problem-solving.

Demonstrate your ability to prioritize by discussing techniques you use to assess the urgency and importance of tasks. Explain how you communicate with stakeholders to manage expectations and ensure all priorities are met effectively.

Discuss specific administrative tools you've used, such as Google Workspace, project management software, or organizational apps. This shows your technical skills and readiness to integrate into Tailscale's operational framework.

You can share your understanding of the importance of confidentiality in an administrative role. Discuss your previous experiences handling sensitive information and your strategies for ensuring data privacy.

Provide an example that illustrates your communication skills and diplomacy. Discuss how you approached the situation respectfully, sought to understand their perspective, and worked towards a positive resolution.

Discuss your method for setting clear agendas, ensuring relevant stakeholders are invited, and following up with notes and action items. Your answer should reflect your organizational skills and focus on efficiency.

Explain how you assess deadlines and prioritize tasks based on urgency and importance. Discuss tools you might use to stay organized and ensure all projects are completed on time.

Share your strategy for managing email communication, such as screen criteria for importance, drafting clear and concise replies, and maintaining the executive's voice while being professional.

Detail your experience with travel planning, including how you factor in preferences, schedule flexibility, and contingencies for unexpected changes. A well-organized travel itinerary reflects your ability to manage details and logistics effectively.

Use this as an opportunity to express your passion for supporting teams, your enthusiasm for Tailscale’s mission, and how you believe your skillset aligns with the company’s culture and needs.