Trust & Safety Manager

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.

About The Role: 

Outschool is seeking a Trust & Safety Manager to lead and scale our Trust & Safety team. This leader will be responsible for ensuring Outschool remains the safest, most trusted learning marketplace for K–12 learners, families, and educators.

This role requires a unique blend of strategic vision, team mentorship, and operational rigor:

• Strategic thinker : Shape a compelling vision for how Trust & Safety can become a competitive advantage and differentiator in K–12 learning.
• Manager as mentor : Guide a talented, domain-knowledgeable team, coaching them to increase their impact and supporting their professional growth.
• Strong operator : Build structure and visibility into team processes, driving efficiency, consistency, and measurable impact across operations.
• Innovator : 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. At Outschool, our titles focus on impact rather than hierarchy.

Core Responsibilities:

• 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.
• Create and refine processes to improve operational effectiveness, efficiency, and visibility .
• 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.

Desired Experience & Skills: 

• 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.
• Experience mentoring and developing team members.
• Operational excellence — strong track record of refining workflows, setting metrics, and creating scalable processes.
• Exceptional communication, conflict resolution, and discretion in handling sensitive matters.
• 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. For New York and California candidates, as well as candidates based in Seattle, WA, the annual salary range for this role is $140,000 - $192,000. For Washington candidates outside of Seattle, as well as Colorado candidates, the salary range for this role is $135,000 - $185,000.

We use Covey as part of our hiring and / or promotional process for jobs in NYC and certain features may qualify it as an AEDT. As part of the evaluation process we provide Covey with job requirements and candidate submitted applications. We began using Covey Scout for Inbound on March 21, 2024.

Please see the independent bias audit report covering our use of Covey here .

Benefits & Culture:

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, retirement plans.
• Health & Wellness: Comprehensive medical, dental, vision, disability, and life insurance — plus fertility/family planning coverage and access to ModernHealth coaching & therapy.
• PTO & Family Benefits: Generous PTO and family leave policies.
• Hybrid & Remote-Friendly: Outschool has a distributed team across the U.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.
• Lifelong Learners: Annual budgets for professional development and DEI learning; budgets for children to take Outschool classes.
• Community Impact: Outschool matches employee donations to eligible charities and supports Outschool.org’s nonprofit 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. 

If you require a reasonable accommodation to participate in the job application or interview process, please contact View email address on swooped.co .

Benefits packages are included for full-time employees only. Please note benefits and perks may vary for employees based outside of the US and Canada.

Full-time employees must be a citizen or legal residents of the U.S. or Canada and reside in U.S. or Canada, unless specifically indicated otherwise. 

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.