Outschool

• Own Paid Search & Emerging Ad Channels • Design and execute the global paid search strategy across Google, Bing and ChatGPT ads - including keyword architecture, match type strategy, bid management, and campaign structure tied to CAC and acquisition goals • Manage day-to-day campaign operations: ad copy refresh, budget pacing, Quality Score optimization, and conversion tracking hygiene • Own Performance Max campaigns, understanding when and how to deploy them alongside traditional search to maximize coverage and efficiency • Use AI to Move Faster • Use AI tools (e.g., ChatGPT, Gemini, or similar) to speed up everyday tasks like drafting ad copy variants, building keyword lists, summarizing performance, and structuring reports • Stay current on how AI is reshaping search - including Performance Max, AI Overviews, and Smart Bidding - and bring a point of view on what it means for how we work • Reduce repetitive manual work over time by building more scalable workflows, even if that starts simple • Drive Performance Analytics • Analyze campaign performance regularly and generate clear, actionable insights for cross-functional stakeholders and leadership • Build and maintain dashboards that give real-time visibility into pipeline contribution, CAC, ROAS, and channel efficiency • Design and execute A/B tests on ad copy, landing pages, and bidding strategies with statistical rigor; communicate results and scale winners • Collaborate Cross-Functionally • Partner with the Senior Performance Marketer owning paid social and teams to ensure messaging consistency and share learnings across channels • Work with data and product to align on attribution methodology, first-party audience signals, and landing page optimization

• Lead, mentor, and grow a small but mighty data team while remaining hands-on with data architecture, modeling, technical direction, and analytics • Contribute directly as an individual contributor, particularly in data engineering, data infrastructure, and analytics engineering, helping establish high standards for data quality, reliability, and usability • Lead data strategy and execution across Outschool’s core data systems, including Redshift, dbt, and Opensearch, and self-serve tools such as Omni, Amplitude, and Statsig • Partner cross-functionally with Product, Engineering, Marketing, Operations, Finance, and other teams to deliver trusted, decision-ready data resources and analytics • Collaborate with senior leadership to align on strategy, priorities, metrics, experimentation practices, and long-term roadmap planning • Foster a culture of data quality, ownership, documentation, self-service, experimentation, and continuous improvement through mentorship and feedback • Lead adoption of self-serve data practices across the organization, ensuring teams can access and use data effectively without requiring significant centralized support • Help define and implement modern data practices that improve speed, trust, discoverability, and leverage across analytics, experimentation, and applied AI / ML

Title: Senior Software Engineer, Infrastructure Location: Haeundae-gu, Busan, South Korea Job Description: 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. The Role We're looking for a Senior Software Engineer, Infrastructure to join our Infrastructure and Platform team. Our core infrastructure team's mission is to empower developers through reliable, secure, and frictionless systems that accelerate innovation and ensure operational stability. You'll own hard problems, including developer experience, automation, security hardening, and evolving our systems to be AI-native. We are an effective team of engineers distributed across the US, Canada, and South Korea. Our philosophy is to start small and then intentionally iterate to test our assumptions and learn quickly. We're iteratively building up a complex product for a highly engaged audience. This role requires working in our Haeundae, Busan, South Korea office, Tuesday-Friday from 7:00 AM to 3:00 PM. Our Stack: - Infrastructure & Platform: - AWS (EKS, RDS, S3, Lambda, VPC, IAM) · Terraform · GitLab · Prometheus/Grafana · OpenTelemetry - Product Layer - TypeScript · Node · React · GraphQL · PostgreSQL · OpenSearch - You won't own this code but you'll own the systems that let engineers ship it with confidence. - AI-Native - The team uses AI throughout the development workflow. - We're actively building infrastructure for AI/ML workloads in production — experimentation pipelines, model serving, and observability. Core Responsibilities: - Developer experience: Define and drive the Developer Experience strategy for a 10-20 person engineering org. Improve tooling, CI/CD pipelines, and internal developer platforms so engineers ship faster and with more confidence. - Automation: Design and implement automation for provisioning, monitoring, deployment, and operational workflows. Reduce toil. Build systems that run themselves. - Security: Harden infrastructure across the stack. Implement security best practices at the platform level. Partner with engineering to embed security into the development lifecycle. - AI-forward infrastructure: Help evolve our platform to natively support AI/ML workloads. Think infrastructure that enables experimentation, scales AI features to production, and supports a team that uses AI as a first-class tool. - Reliability: Own production systems. Build observability into everything. Set the reliability bar and on-call culture for the engineering org. Participate in on-call and lead incident response with a systems-thinking mindset. Desired Experience and Skills: - 7+ years of software or infrastructure engineering experience - Deep experience with AWS: EC2, EKS, S3, Lambda, RDS, VPC, IAM, and related services - Strong Kubernetes fundamentals: deployment, scaling, networking, workload management, and debugging containerized services - Infrastructure as Code with Terraform - Experience building and maintaining CI/CD pipelines (GitHub Actions, ArgoCD, or similar) - Familiarity with observability stacks: Prometheus, Grafana, Honeycomb, OpenTelemetry (or similar) - Strong grasp of distributed systems concepts: consistency, fault tolerance, replication, and delivery semantics - AI-forward approach: you actively use AI tools in your workflow. You can prompt well, validate output critically, and know when to override - Intermediate or higher English Reading, Writing, Listening and Speaking skills (our interview process and daily work is conducted entirely in English). Other Considerations: - Experience in EdTech or building products for learners, educators, or families - Familiarity with search and discovery systems - Familiarity with payment APIs (e.g. Stripe) - Background in marketplace technologies - Experience at a fast-paced startup or high-growth company Compensation: Outschool recruits across the US, Canada, and South Korea and sets employee salaries to reflect local compensation and cost of living. This role is available in South Korea: The salary range for this position is 63,125,700 - $78,907,125 KRW annually. Benefits in South Korea: - Coworking Office located directly at exit 11, Jangsan Station in beautiful Haeundae, Busan. - Necessary equipment (MacBook, monitor, etc.) and software for work provided - Finish work early in the day - working hours from 7AM - 3PM. - Flexible vacation, use whenever you like. Korean national holidays plus 15 extra days per year. - Invitation to join the annual company retreat once per year (flight to United States, hotel, meals paid for by company). 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. 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.

• Lead, mentor, and grow a team of 5–10 engineers while remaining hands-on with architecture, system design, and technical direction • Contribute directly to the codebase as an individual contributor, helping accelerate development velocity and establish high engineering standards • Lead engineering strategy and execution for a brand-new, high-priority initiative • Partner cross-functionally with Product, Design, Data, Marketing and Operations to deliver an exceptional parent experience • Collaborate with senior leadership to align on strategy, priorities, metrics, and long-term roadmap planning • Foster a culture of technical excellence, ownership, experimentation, and continuous growth through mentorship and feedback • Lead adoption of AI-development principles and agentic engineering workflows across the organization • Help define and implement modern engineering practices that leverage AI to improve developer speed and productivity, and product quality

• Drive complex, high-impact engineering initiatives across personalized discovery, payments, reimbursement workflows, supply eligibility, and other related problem spaces • Partner closely with Product, Design, Data, and Engineering leadership to align on roadmap priorities, technical tradeoffs, risks, and execution strategy • Demonstrate AI-native development mindset leveraging fully agentic development workflows, while also contributing to establishing principles and best practices on AI development • Mentor engineers and influence technical direction across teams through strong collaboration, communication, and domain expertise • Participate in stand-ups, sprint planning, retros, production deployments, and on-call rotations

• Act as a critical contributor to developing key products from Outschool, participating and demonstrating exemplary proficiency in domain understanding, user empathy, engineering design, system quality, and cross-functional collaboration • Execute true 0-to-1 efforts with an innovative and action-oriented mindset, embracing ambiguity as an opportunity rather than a challenge • Lead Outschool’s AI-native development transformation both as a cross-team lead and as a deep IC who leads by example • Take on people management responsibilities as needed, like day-to-day support, performance management, and career development • Act as a senior engineering leader to shape Outschool’s engineering culture and processes, particularly with an AI angle • Contribute to hiring by helping identify, interview, and onboard strong engineering talent • Participate in stand-ups, sprint planning, retros, production deployments, and on-call rotations

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: As part of the CX team, you'll handle escalated tickets from parents and teachers - the ones without an obvious answer, where you'll be making independent judgment calls without a playbook for every situation. You'll also occasionally handle Trust & Safety escalations, which can include sensitive content. We're looking for someone with strong investigative, decision-making, and writing skills who thrives on resolving complex, ambiguous issues in a fast-paced environment. Core Responsibilities: - Resolve escalated customer support tickets from parents and teachers, primarily via email - Investigate ambiguous situations and make sound decisions under time pressure - Handle occasional Trust & Safety escalations, which may involve sensitive content including reports related to minors, self-harm, or abuse - Communicate outcomes clearly and with care, including when the answer isn't what the customer hoped for - Share useful context and feedback from your ticket work with the broader CX team Desired Experience & Skills: - Strong written communication, especially for difficult or sensitive conversations - Judgment under ambiguity: you can make a decision, explain your reasoning, and keep moving - Able to engage with occasional heavy content without it derailing your work - Comfortable working independently in a remote, fast-paced environment Nice to Haves: - Experience in K–12 education - Startup experience - Prior experience with escalated support tickets - Prior exposure to Trust & Safety, content moderation, or other judgment-heavy work Hours and Compensation: - Outschool recruits across the U.S. and Canada. This role is anticipated to work 35-40 hours per week, with an anticipated hourly rate of $25.00. Benefits: - This is a contract role. As a contractor, benefits are not included; however, a full benefits package would be available if converted to a full-time employee. 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 recruiting@outschool.com. 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.

This description is a summary of our understanding of the job description. Click on 'Apply' button to find out more. Role Description Outschool is looking for a strategic, impact-seeking Lead Counsel, Product & Commercial to join our Legal team. This is a highly visible role for a business-minded lawyer who thrives at the intersection of product development, commercialization, and regulatory risk. You will serve as the primary legal partner to Product teams, supporting all stages of product development, launches, and monetization, while also leading Outschool’s commercial legal function. You’ll be a trusted advisor to cross-functional leaders, known for delivering practical, creative, and timely guidance that enables the business to move forward thoughtfully and compliantly. You are a jack-of-all-trades who thrives in a dynamic environment, balancing multiple high-impact initiatives with strong execution, sound judgment, and timely delivery. While titled “Lead Counsel” at Outschool, this role is equivalent in scope and responsibility to a Director-level role at many companies. You are energized by complexity, enjoy being hands-on, and are excited to help scale a mission-driven, kid-focused platform. Core Responsibilities - Product & Regulatory Counsel - Serve as the primary legal advisor to Product, Engineering, Marketing, Trust & Safety, and Operations teams, partnering across the product lifecycle to embed legal and compliance considerations into product decision-making. - Spot and analyze legal issues across consumer protection, privacy and data protection, employment and independent contractor considerations, trust & safety, litigation risk, and other regulatory requirements. - Review global products, features, platforms, and initiatives to provide practical, risk-based guidance across multiple jurisdictions. - Advise senior leadership on complex, high-impact matters and drive cross-functional alignment on strategic initiatives. - Ability to work across the organization and with all levels of different internal stakeholders. - Commercial & Operational Legal Leadership - Lead Outschool’s commercial legal work, including reviewing and negotiating vendor agreements, advising on legal terms for marketing and growth initiatives, and managing outside counsel. - Develop and maintain scalable templates, playbooks, and processes to support operational efficiency. - Knowledge and ability to assist with other legal projects on an as-needed basis. Qualifications - 7+ years of combined law firm and in-house experience (including at least 4 years in-house), with significant responsibility advising on product and commercial matters. - Active membership in at least one U.S. state bar (or eligibility to register as authorized in-house counsel). - Proven ability to distill complex legal issues into clear, actionable guidance that business partners can operationalize. - Strong analytical skills and sound commercial judgment, with the ability to balance legal risk and business objectives, and exercise impeccable judgment in identifying when to escalate issues or engage internal stakeholders and outside counsel. - Excellent communication, writing, and influence skills, with experience working cross-functionally and leading complex matters end-to-end. - SF or NYC candidates preferred for hybrid work, with flexibility for remote. Other Considerations - Experience advising on both B2C and B2B products. - Background in high-growth technology companies, marketplaces, or platforms, including familiarity with independent contractor or gig-economy issues. - Experience with kid-focused or education-related consumer products and COPPA. - Interest in or experience advising on generative AI or other emerging technologies. Benefits - 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.

• Provide high-quality product support to parents and teachers, primarily via chat and email • Resolve customer inquiries with empathy, clarity, and sound judgment • Handle more complex or sensitive support situations, escalating internally when appropriate • Follow established workflows while adapting to new products, tools, and policies • Take on additional CX-related tasks as needed to support team operations