Head of Engineering


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.

Our business is growing explosively and as of August, 500,000 learners have taken more than over 2M class hours. We've more than tripled our team since the beginning of 2020 from 25 to 80 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 outschool.org to offer financial assistance to families in need.


We’re looking for an inspiring, impact-seeking engineering leader to level up our engineering org and help grow our company as part of the exec team. You’ll use all of your distinctive experience and talent to have an impact at a key inflection point in our company’s history and in the evolution of the education system.  We have a great start and now we need your help to build a great organization, for a greater purpose. If you’re passionate about learning, enabling others, and having a positive impact on education, we’d love to hear from you.


  • Help drive Outschool’s strategy as a key member of the executive team.
  • Lead our engineering org and grow it from thirty to hundreds of engineers in 3 years.
  • Build culture and team, enable and develop engineers and managers in a fast-paced and constantly changing environment.
  • Partner closely with product, design, marketing, and other functions to create a world-class service that inspires kids to love learning.
  • Drive technology and data innovation to enable breakthrough customer features.
  • Plan and organize to balance product development, infrastructure investments, and technology innovation.
  • Carry forward Outschool’s cultural values and champion diversity, equity and inclusion.


  • You are an inspiring leader who is committed to learning, growing, and enabling others.
  • You have a track record of building and leading diverse teams.
  • You have experience leading engineering teams of 50+ and growing teams 2-3X per year in a fast-changing startup environment.
  • You have strong communication and collaboration skills.
  • You have a track record of enabling career development and high performance.
  • You have had responsibility for strategic planning for a department, including identifying new organizational needs and creating hiring plans or frameworks to meet them.
  • You are a respected technical leader and can enable effective technical decision-making.
  • You have a track record of partnering with product and other functions to deliver customer value and business impact at scale.


  • Experience managing remote teams is a plus.
  • Education or marketplace experience is a plus.
  • Prior experience as a member of an executive team is a plus.


  • 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 Outschool.org 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 recruiting@outschool.com. Must be a citizen or legal resident of the U.S. or Canada and reside in U.S. or Canada.