The Company

Outschool’s mission is to inspire kids to love learning. We achieve this by linking learning to kids’ interests, connecting them with other classmates who share their passions, and giving them the autonomy to pick their own paths. Our small group classes meet over live video chat with teachers who celebrate their unique strengths and empower all learners to develop confidence and a strong sense of self.
We’re also focused on removing barriers for historically underserved learners who face systemic challenges to their success. Outschool.org is a nonprofit that partners with homeschooling co-ops, community-based organizations, and schools across the U.S. to provide marginalized communities with access to virtual and hybrid learning experiences.
We believe that diversity drives learning. To meet our mission, we encourage, support, and celebrate different ideas, perspectives, and backgrounds. As a fully distributed (remote) team, we challenge one another to find the most effective way to empower learners, teachers, and parents. Your name, race, religion, gender, nationality, sexual orientation, and age are not barriers; they are why we want to work with you. We invite talented and creative candidates who value the importance of nurturing a child’s boundless curiosity to join us on this journey.
The pandemic has been challenging for families all over the globe. We acted quickly and worked together to provide quality resources to learners, parents, and teachers in the past year. As communities worldwide rethink their approach to education, Outschool will continue to innovate and provide kids with unique opportunities to explore their passions.

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. 

The Role

As Outschool’s Trust and Safety Lead, you will come up with and work cross-functionally to implement scalable solutions to identify, monitor, and prevent bad actors from using Outschool.  You will help shape and operationalize processes related to privacy, marketplace risk, and other safety-related issues as we scale. You will also be on the front lines answering tickets with inquiries and concerns, where you will investigate trust and safety incidents that arise on our platform, as well as handle complex social-emotional issues that emerge during classes. Your detail-oriented habits mean you leave no stone unturned, and your experience in online investigations means you find relevant details others may miss. You are tenacious when it comes to meeting your goals and supporting your team, and you are able to thrive in a fast-paced startup environment. You care about keeping kids safe and have demonstrated this commitment in either your prior work or interests.

This role requires a schedule that includes some on call days on weekends, as well as some holiday coverage (split on a rotating basis with teammates)


    • Propose operational improvements and scalable solutions to Trust and Safety concerns, then take the lead in partnering with other teams to implement those improvements and solutions.
    • Partner with the Product team to define, prioritize, and implement the most impactful Trust and Safety initiatives.
    • Conduct investigations and successfully resolve and document trust and safety cases primarily through chat functions or email, but sometimes over the phone in a timely manner.
    • Utilize investigations, metrics, and data analysis to identify trends and anticipate risks on the Outschool platform.
    • Leverage your experience in handling customer concerns and work with your team to come up with operational improvements that scale the team’s impact without compromising customer safety.
    • Multi-task and prioritize time-sensitive and high risk safety incidents, while maintaining operational excellence and standards in responding to those situations.


    • 4 + years experience in either trust and safety or high risk customer support or operations, ideally at a high growth startup, where the scope of the role involved working cross-functionally to implement ways to solve problems at scale.
    • An interest in educational issues and a dedication to children’s safety/security concerns including sensitivity to unique/neurodiverse learning needs, awareness of mandatory reporting issues, a commitment to protecting learners in an online environment, and a having basic understanding privacy issues is essential
    • Past work experience with online investigations or fraud detection/loss prevention is a plus.
    • Known for having a superb bedside manner, excellent judgment, and an incredible work ethic, as well as an ability to empathize with customers.
    • Exceptional verbal and written communication and conflict resolution skills.
    • Proven ability to collaborate with stakeholders across multiple functional areas to champion and improve Trust & Safety within the platform.

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 $135,000 – $160,000 USD.

For Washington candidates outside of Seattle, as well as Colorado candidates, the salary range for this role would be $121,000 – $144,000 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 Outschool.org’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 recruiting@outschool.com 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.