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Head of People



People & HR
Remote · United States · Canada
Posted on Tuesday, April 2, 2024

The Company

Outschool’s mission is to inspire kids to love learning. In our fast-changing world, the traditional educational system struggles to meet the diverse and evolving needs of young learners. Outschool reimagines this system, offering flexible and engaging learning experiences as a supplement and alternative to traditional education. By connecting learners with a global community of teachers and peers through our online platform, we make learning personal, dynamic, and deeply human.

We've made significant strides since launching our marketplace of live online classes in 2017. Finding initial success with secular homeschoolers, we then expanded to enrichment learning to meet the needs of a wider audience, growing our business 16x since 2019. Post-pandemic, we have evolved our platform to power academic learning, incorporated AI, and have begun to grow our international community. We're proud to have served over 1M passionate learners with more than $100M in annual bookings.
Driving disruptive, positive change in education is rewarding and hard. Outschool team members are encouraged to challenge themselves, take risks, and grow in their careers. We look for talented people whose sense of urgency, innate curiosity, and determination to drive impact will help Outschool achieve outsized results in pursuit of our mission. We invite you to be part of an ambitious team dedicated to ensuring every learner can navigate the future with curiosity, resilience, and a love of learning.

Outschool has been named Fast Company’s most innovative EdTech company in the world, and one of the top ten best startups for women from Elpha. Outschool has also been one of BuiltIn’s Best Remote Places to Work for the last two years and has appeared on Y Combinator’s Top Companies list for the last three years.

About the Role

As the Head of People, you will play a pivotal role in transforming our talent and culture to establish a world-class team shaped by ambition, high velocity, resilience, learning & experimentation. Reporting to the Head of Operations, you will combine strategic vision and operational efficiency to propel Outschool towards greater success during an exciting growth phase.

Your mission will be to cultivate a workplace that is not only operationally excellent but also fosters innovation and continuous professional growth. Your leadership will be instrumental in making Outschool a place where big goals and informed risks are encouraged, failures lead to learning, and every team member is empowered to contribute to our mission. Through your strategic initiatives, you will drive Outschool's growth by fostering a culture where both the organization and its people thrive.

Core Responsibilities:

  • Develop a comprehensive People strategy that marries operational excellence with a culture of continuous learning, improvement, and ambition.
  • Enhance our talent acquisition and development processes to attract and develop individuals who are not only exceptionally talented but also deeply committed to our mission and culture of growth and continuous improvement.
  • Design and implement developmental initiatives that prioritize experiential, hands-on learning, encouraging team members to take ownership, innovate, and push boundaries.
  • Lead by example in change management, promoting a mindset of growth and adaptability, while guiding the team through organizational evolutions with clarity and strategic alignment.
  • Foster an employee experience that amplifies engagement and cultural unity, especially in a remote working environment, through strategic programs and practices.
  • Streamline People operations to ensure alignment with Outschool’s goals, focusing on impact and efficiency while adhering to compliance standards.
  • Proactively manage employee relations and risk management, fostering an environment of open feedback and collaboration that supports a dynamic and innovative work culture.

Desired Experience & Skills:

  • Demonstrated leadership in the People function with a balanced approach to operational excellence and fostering an innovative, learning-centric culture in a growth-oriented, tech-savvy environment.
  • Deep expertise in developing People strategies that effectively blend best practices with a forward-looking approach to workplace innovation.
  • Strong business acumen and strategic thinking, with the ability to integrate broad perspectives into actionable, growth-oriented plans.
  • Excellent communication and influence skills, capable of engaging and motivating across all levels of the organization, building an inclusive, collaborative culture.
  • A commitment to data-driven decisions, adept at balancing efficiency and impact in all People operations.
  • Experience in leading a diverse, remote workforce, creating strategies that offer flexibility while ensuring strong alignment and productivity.
  • Skilled at navigating change, fostering a culture of resilience, and managing transformations with strategies that align incentives and communication clearly.

Outschool recruits across the US and Canada, and sets employee salaries to reflect local compensation and cost of living. For New York and California candidates, as well as candidates based in Seattle, WA the salary range for this role would be $225,000-$ 325,000 USD.

For Washington candidates outside of Seattle, as well as Colorado candidates, the salary range for this role would be $202,500-$292,500 USD.




At Outschool, we believe that taking care of one another enables us to do our best work. To us that means:
Shared Financial Success: Competitive salaries, stock options, and investment plans that make saving for retirement easier.
Health & 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 & 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.
Fully Distributed: With a team distributed across the US and Canada, we create a remote culture through expensable 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 charities and has committed to support’s non-profit programs.
Outschool is an equal opportunity employer. We view diversity as a moral imperative and 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 neurodiverse individuals, applicants with physical and mental disabilities, and disabled veterans. For individuals who would like to request an accommodation, you may reach out to us at or through your Recruiting point of contact as you schedule your initial interview.
Benefits packages are included for full-time employees only.
Full-time employees must be a citizen or legal residents of the U.S. or Canada and reside in U.S. or Canada.
Once you submit your application, Outschool will process your personal data to evaluate your candidacy for employment. Unless specifically indicated otherwise, we hire employees only in the U.S. and Canada. Applicants else where should be aware that we may discard your application upon submission or we may ask if you would like us to retain it later should there be consideration (this is not typical at all). If you are selected for interviewing, your data will be shared with interviewers and personnel involved in that process. If not hired, your application will be retained for one year in case there is another suitable role. You may opt out of this at any time. Please see our Employee/Applicant Privacy Notice for more detailed information. If applicable, as you progress through the process, we will be clear about what information is being asked for and what happens with that information.