Director of Engineering

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 1.5M 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 hiring a Director of Engineering to lead a strong product engineering team developing Outschool’s mission-critical products, including and in particular a new AI-powered platform that transforms how families are able to navigate the complex world of alternative education while getting reimbursed through public-funding programs. This role will be responsible both for developing 0-to-1 products from the ground up, as well as scaling user journeys on Outschool’s existing marketplace. This is a highly impactful leadership role that combines technical strategy, people leadership, and hands-on development. The ideal candidate will shape not only Outschool’s most critical products, but also our engineering culture, talent growth, as well as AI-native development models, all while delivering meaningful educational impact to millions of families. Core Responsibilities: 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 Desired Experience & Skills: 10+ years of software engineering experience 5+ years of engineering management experience leading medium-sized teams, with demonstrated proficiency in performance management, career development, and people logistics Familiar with AI-native development paradigms and understands how to take teams through AI transformations Strong experience with full-stack development: TypeScript, React, Node.js, GraphQL, and PostgreSQL Experience balancing engineering leadership responsibilities with hands-on coding and technical contribution Proven ability to lead multiple complex initiatives from planning through execution and d