Outschool’s mission is to inspire kids to love learning. 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. 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. 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. Outschool is seeking a Trust &

• Safety Manager to lead and scale our Trust &

• Safety team. Shape a compelling vision for how Trust &

• Safety can become a competitive advantage and differentiator in K–12 learning. Guide a talented, domain-knowledgeable team, coaching them to increase their impact and supporting their professional growth. Partner with Product and Engineering to leverage the latest in AI and large language models (LLMs) to solve Trust &

• Safety challenges in new and scalable ways. At other companies, this role would align with a Senior Manager position. Develop and execute a comprehensive Trust &

• Safety strategy that aligns with Outschool’s mission and positions safety as a differentiator. Lead, mentor, and inspire a small but skilled team, helping them grow professionally and amplify their impact. Use data and analytics to identify risks, measure program effectiveness, and continuously improve workflows. Partner with Legal, Product, and Engineering to design policies, tools, and scalable solutions to prevent and respond to safety incidents, fraud, and misconduct.



Address sensitive community issues with discretion and empathy. Stay ahead of industry trends, regulations, and technology to proactively identify areas of risk and opportunity. Ensure clear communication and training to build a culture of safety across the company and our educator/learner community. 5+ years leading Trust &

• Safety teams in technology, education, or marketplace platforms. ~ Strong understanding of online safety, privacy, compliance, and risk management. ~ Proven ability to use data and analytics to inform decisions and measure impact. ~ Passion for Outschool’s mission and for building safe, supportive communities for kids and educators. Outschool recruits across the US and Canada, and sets employee salaries to reflect local compensation and cost of living.

Shared Financial Success: Competitive salaries, stock options, retirement plans.

Health & Wellness: Comprehensive medical, dental, vision, disability, and life insurance — plus fertility/family planning coverage and access to ModernHealth coaching & therapy. Generous PTO and family leave policies. Hybrid & Remote-Friendly: S. and Canada and a new office in San Francisco.

Bay Area–based employees work in the office part of the week and receive commute-related benefits. Team members outside the Bay Area remain fully remote, with support for expensable home office setup, internet, and weekly meals to stay connected no matter where you are. budgets for children to take Outschool classes.

Community Impact: 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.

Benefits packages are included for full time employees only. Full-time employees must be a citizen or legal residents of the U.Once you submit your application, Outschool will process your personal data to evaluate your candidacy for employment. If you are selected for interviewing, your data will be shared with interviewers and personnel involved in that process.

📌 Remote Trust & Safety Manager (Whitby)
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📍 Whitby