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Executive Assistant

USAFull-Time$120K - $140K
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About Tailscale 

Tailscale builds software that makes it easy to securely interconnect people and their devices, no matter where they are. From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more. We’re building a future for the Internet that’s easy, small and safe, like it used to be. Founded in 2019 and fully distributed, we’re backed by Accel, CRV, Insight, Heavybit, and Uncork Capital. 

Job Description

Tailscale is looking for a detail-oriented, hyper-organized Executive Assistant to support our Chief Operating Officer. The Executive Assistant to the COO will provide best-in-class administrative support and help keep our COO and his business functions organized and laser-focused. We’re looking for an individual who can think on their feet, enjoys collaborating with highly technical teams, and is comfortable working and executing asynchronously.

To perform this job successfully, the individual is expected to handle highly sensitive and confidential financial, legal, personnel and institutional information while exercising professionalism and discretion.

Are you excited to nurture positive relationships and help set our team up for success? If so, we’d love for you to apply!


  • Directly support the Chief Operating Officer by maintaining focus and eliminating distractions
  • Collaborate extensively with the leadership team while taking ownership of various responsibilities
  • Manage the COO’s professional calendar, ensuring purposeful meetings with clear agendas and prepared attendees
  • Provide administrative support by creating, editing, and facilitating presentations (including slide decks, spreadsheets, and other documents) for the COO to help drive initiatives and programming
  • Establish and maintain a comprehensive filing system, ensuring accessibility for the executive team
  • Prioritize and assign work to department staff based on delegated authority
  • Respond to inquiries or refer them to the appropriate partner both internally and externally
  • Respond to inquiries, attend meetings as a note-taker, and facilitate agenda items
  • Collect, prioritize, and propel the execution of key decisions
  • Arrange detailed domestic and international travel plans and itineraries
  • Additional administrative functions include creating expense reports, planning for and assisting with offsites, and the preparation of documents for signature and presentations
  • Prioritize conflicting requests and needs and handle matters proactively, swiftly, and to completion while meeting deadlines
  • Take a team-oriented approach and provide assistance to other Executive Assistants as required
  • Review, prioritize, and (using your discretion) respond to emails on the COO’s behalf
  • Periodic travel, approximately once a quarter, to support executive needs and enhance collaboration with key stakeholders


  • Previous experience at a high-growth, fast-paced startup, in which you have provided administrative and logistical support to startup founders, leadership, or executives
  • A proactive and resourceful approach to your work - you’re a natural problem solver with an ability to think on your feet and propose alternative solutions
  • Excellent organization, time management, and both written and verbal communication skills
  • Good business judgment - you know when to escalate issues upward and when to apply common sense
  • Acute attention to detail - you’re extremely organized, with a knack for noticing and remembering the small stuff
  • A people-first mentality and the ability to anticipate needs and preferences
  • Experience giving and receiving constructive feedback and working independently
  • Flexibility to adjust to the dynamic nature of a startup
  • Note: this position will require you to work during the same business hours as the COO (9:00a - 5:00p ET, Monday - Friday). Travel and off hours are sometimes required
  • Familiarity with the Google Workspace product suite (Nice to Have)
  • Experience working with a legal, finance, and sales executives (Nice to Have)
  • Experience engaging with engineering teams (Nice to Have)
  • Familiarity with building systems in Notion (Nice to Have)
  • Experience working with globally-distributed teams (Nice to Have)

For this position, our target salary range is $120,000-$140,000 USD (paid in your local currency). As a company, we strive to maintain fair and equitable compensation practices within our team across all roles and all levels.

What We Offer

  • An inclusive, flexible environment where you can be your authentic self. We recognize the impact diverse voices and backgrounds have on the growth of our people, our product, and our company. And that flexibility in how and when you work empowers our team to balance work and life.
  • A competitive total compensation package. This includes base salary and an equity incentive plan.
  • Comprehensive group benefits with no waiting period. Take advantage of coverage for health, vision, dental, and more for you and your family!
  • Remote-first with the opportunity to work from anywhere—enjoy a change of scenery wherever you can get wifi and join our company retreats with fellow Tailscalars!
  • Support for your personal and professional development. Grow your career thoughtfully with $1500 USD annually for professional development, leverage our conference budget to learn from experts in your field, or take advantage of mentorship, coaching, and internal promotion opportunities. 
  • Paid time off and a healthy work-life balance. Take advantage of 4 weeks of vacation each year, uncapped sick time when you need it, and support for any situation life throws your way!
  • A build-your-own home office setup. You choose your own company-owned laptop (MAC or PC), receive a monthly home internet reimbursement, and $1000 USD to customize your workstation to make it your own. 
  • Generous parental leave program from your first day. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups for up to 26 weeks. 

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