Tailscale is looking for a proactive and engaging Executive Assistant to support our Chief Technology Officer to provide both personal and professional administrative support. From planning and directing all administrative activities, to supporting our team with offsites and team bonding activities, your support will be essential to keeping the Engineering Organization and its leaders operating efficiently and effectively  Because we’re an early-stage and fully remote company, we’re looking for an individual who can think on their feet, enjoys collaborating with highly technical teams, and is comfortable working asynchronously.

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

You will:

  • Keep the Chief Technology Officer laser-focused by removing and unblocking any and all distractions. As such, this role involves heavy collaboration with the leadership team in addition to an ownership mindset.

  • Maintain personal and professional calendars in a thoughtful and purposeful manner, ensuring meetings contain the appropriate attendees, agenda items, and are aligned with top priorities

  • Analyze and work to deeply understand the goals, and help drive schedules accordingly.

  • Collect, prioritize, and drive the execution of key decisions.

  • Arrange complex and detailed domestic and international travel plans and itineraries.

  • Communicate directly, on behalf of the leadership team, with external and internal stakeholders.

  • Additional administrative functions include 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.

  • Assist the CTO with ad hoc projects and support, including personal events and family needs.

  • Be located in the Bay Area and have intimate knowledge of the Bay Area.

Ideally, you have:

  • Previous experience at a high-growth, fast-paced startup, ideally 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 interpersonal 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.

  • This position will require you to work during business hours (travel, off hours and OT also involved)

It’s nice if you have:

  • Familiarity with the Google Workspace product suite.

  • Experience engaging with engineering teams.

  • The ability to quickly learn new tools and technologies.

  • Experience working with globally-distributed teams.


Please keep reading...

Research shows that candidates from underrepresented backgrounds often don't apply for roles if they don't meet all the criteria — unlike majority candidates meeting significantly fewer requirements.

We strongly encourage you to apply if you’re interested: we’d love to know how you can amplify our team with your unique experience!

About Tailscale

Tailscale builds software that makes it easy to connect and secure devices, no matter where they are. Every day, banks and multi-national companies use Tailscale to protect their corporate networks. Hobbyists and start-ups trust Tailscale to collaborate and share access to tooling. 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, HeavyBit, and Uncork Capital. 

Apply for this Job

* Required
resume chosen  
(File types: pdf, doc, docx, txt, rtf)
cover_letter chosen  
(File types: pdf, doc, docx, txt, rtf)

Voluntary Self-Identification

For government reporting purposes, we ask candidates to respond to the below self-identification survey. Completion of the form is entirely voluntary. Whatever your decision, it will not be considered in the hiring process or thereafter. Any information that you do provide will be recorded and maintained in a confidential file.

As set forth in Tailscale’s Equal Employment Opportunity policy, we do not discriminate on the basis of any protected group status under any applicable law.

Race & Ethnicity Definitions

If you believe you belong to any of the categories of protected veterans listed below, please indicate by making the appropriate selection. As a government contractor subject to the Vietnam Era Veterans Readjustment Assistance Act (VEVRAA), we request this information in order to measure the effectiveness of the outreach and positive recruitment efforts we undertake pursuant to VEVRAA. Classification of protected categories is as follows:

A "disabled veteran" is one of the following: a veteran of the U.S. military, ground, naval or air service who is entitled to compensation (or who but for the receipt of military retired pay would be entitled to compensation) under laws administered by the Secretary of Veterans Affairs; or a person who was discharged or released from active duty because of a service-connected disability.

A "recently separated veteran" means any veteran during the three-year period beginning on the date of such veteran's discharge or release from active duty in the U.S. military, ground, naval, or air service.

An "active duty wartime or campaign badge veteran" means a veteran who served on active duty in the U.S. military, ground, naval or air service during a war, or in a campaign or expedition for which a campaign badge has been authorized under the laws administered by the Department of Defense.

An "Armed forces service medal veteran" means a veteran who, while serving on active duty in the U.S. military, ground, naval or air service, participated in a United States military operation for which an Armed Forces service medal was awarded pursuant to Executive Order 12985.

Form CC-305

OMB Control Number 1250-0005

Expires 05/31/2023

Voluntary Self-Identification of Disability

Why are you being asked to complete this form?

We are a federal contractor or subcontractor required by law to provide equal employment opportunity to qualified people with disabilities. We are also required to measure our progress toward having at least 7% of our workforce be individuals with disabilities. To do this, we must ask applicants and employees if they have a disability or have ever had a disability. Because a person may become disabled at any time, we ask all of our employees to update their information at least every five years.

Identifying yourself as an individual with a disability is voluntary, and we hope that you will choose to do so. Your answer will be maintained confidentially and not be seen by selecting officials or anyone else involved in making personnel decisions. Completing the form will not negatively impact you in any way, regardless of whether you have self-identified in the past. For more information about this form or the equal employment obligations of federal contractors under Section 503 of the Rehabilitation Act, visit the U.S. Department of Labor’s Office of Federal Contract Compliance Programs (OFCCP) website at www.dol.gov/ofccp.

How do you know if you have a disability?

You are considered to have a disability if you have a physical or mental impairment or medical condition that substantially limits a major life activity, or if you have a history or record of such an impairment or medical condition.

Disabilities include, but are not limited to:

  • Autism
  • Autoimmune disorder, for example, lupus, fibromyalgia, rheumatoid arthritis, or HIV/AIDS
  • Blind or low vision
  • Cancer
  • Cardiovascular or heart disease
  • Celiac disease
  • Cerebral palsy
  • Deaf or hard of hearing
  • Depression or anxiety
  • Diabetes
  • Epilepsy
  • Gastrointestinal disorders, for example, Crohn's Disease, or irritable bowel syndrome
  • Intellectual disability
  • Missing limbs or partially missing limbs
  • Nervous system condition for example, migraine headaches, Parkinson’s disease, or Multiple sclerosis (MS)
  • Psychiatric condition, for example, bipolar disorder, schizophrenia, PTSD, or major depression

PUBLIC BURDEN STATEMENT: According to the Paperwork Reduction Act of 1995 no persons are required to respond to a collection of information unless such collection displays a valid OMB control number. This survey should take about 5 minutes to complete.