Outschool’s mission is to inspire kids to love learning. We believe the best way to do that is by linking learning to kids’ interests, connecting them with others who share those interests, and giving them the autonomy to pick their own path. We provide small group classes that meet over live video chat where learners are connected with teachers and classmates who share their interests. These classes are offered through our marketplace and conducted on our remote learning platform. Outschool is looking to hire a new executive assistant to join our remote team!

Our business is growing explosively and as of August, 800,000 learners have taken more than over 4M class hours. We’ve more than quadrupled our team since the beginning of 2020 from 25 to 100 to keep up with growth. We’ve raised $57M since founding with most of that still in the bank. Our sales have grown 2000% in the past year to reach a run-rate of more than $100M.

We’re an experienced team with past accomplishments at Airbnb, Square, Apple, Uber, Udemy, Amazon, Wikipedia, Google, and many startups. We came together because we wanted to make a difference in education and saw the opportunity to empower learners, teachers, and parents.

Now, in the face of mass school closures, our product and expertise have become central to many more families, teachers and organizations than ever before. We’re committed to access and impact so we founded to offer financial assistance to families in need.

The Role

At Outschool, our Executive Assistants are thought-partners with their Executive team. You will work closely and strategically with your Executives and their teams by solving problems, crafting communications, and managing relationships. In this role, you will join the People Operations team, reporting to the People Operations Lead, and a company of lifelong learners dedicated to our mission to inspire kids to love learning. We are looking for an EA who is similarly passionate about education, growing, and sharing along with our team. We are a remote-first company dedicated to our employees, and this role will be remote as well.


  • Support the Head of Marketing, Head of Schools & Distribution, and 1-2 additional Outschool executives in calendaring, meeting planning, creating presentations, and other logistics
  • Implement strategies to help Executives work more efficiently, including identifying new tools to use
  • Manage email communications for Executives, including sales outreach emails as needed, and prioritizing and sending correspondence on Executives’ behalf when appropriate
  • Manage special projects by keeping Executives informed of deadlines and project updates
  • Assist with budget management
  • Edit and proofread communications before they are sent out
  • Conduct research
  • Provide support to the Operations team as needed, including help with special projects, events, off-sites, and travel


  • Three (3) years of previous EA or administrative/internal ops roles, preferably at high-growth companies
  • Ability to maintain absolute integrity, and complete discretion
  • Possession of strong organizational, interpersonal skills,
  • Ability to multitask and adapt well to rapidly changing priorities; must be a proactive self-starter and strategic thinker with a demonstrated ability to work freely with minimal supervision
  • Excellent attention to detail, organizational skills, accuracy, and very strong follow through tendencies


  • Experience in marketing or sales is a plus
  • Experience in K-12 education is a plus
  • Familiarity with the following: Google Apps, Slack, Dropbox, HelloSign, Intercom, Trello


  • Shared Financial Success: Competitive salaries, stock options, and a 401k that makes saving for retirement easier.
  • Health and Wellness: Comprehensive health, dental, vision, disability, and life insurance coverage options for employees and their families. Our medical benefits include fertility and family planning coverage. We also provide employees with online access to coaching and therapy sessions through our partner, ModernHealth.
  • PTO and Family Benefits: PTO and family leave enable our team to take the time that we need to recharge, relax, and spend time with family and friends.
  • Remote First: With over 50% of our team distributed across the US and Canada, we create a remote culture through expensable weekly meals, virtual events, expensable home office setup, and internet allowance.
  • Lifelong Learners: Annual budgets to self-direct our professional development as well as DEI learning. There’s also a budget for employees’ learners to take classes on Outschool!
  • Community Impact: Outschool matches employee donations to established 501c3s, and has committed to donating $3M to non-profit programs.

Outschool is an equal opportunity employer. We view diversity as a moral imperative and a competitive advantage. We do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status. We plan and structure our interviews to directly assess skills and experience.

Outschool is committed to providing reasonable accommodations to disabled veterans and applicants with physical and mental disabilities. If you need assistance due to a disability, you may contact us at

Must be a citizen or legal resident of the U.S. or Canada and reside in U.S. or Canada.

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