Director of Engineering

The Company

Outschool’s mission is to inspire kids to love learning. We offer flexible and engaging learning experiences as a supplement and alternative to traditional education, connecting learners with a global community of teachers and peers through our online platform. Since launching our marketplace of live online classes in 2017, we’ve grown significantly, serving over 1.5M passionate learners with more than $100M in annual bookings.

The Role

We’re hiring a Director of Engineering to lead a strong product engineering team developing Outschool’s mission-critical products, including a new AI-powered platform that transforms how families navigate alternative education and get reimbursed through public funding programs. This role combines technical strategy, people leadership, and hands-on development, shaping not only our most critical products but also our engineering culture, talent growth, and AI-native development models.

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
• 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 delivery
• Data-driven mindset with experience leveraging experimentation, A/B testing, analytics, and metrics to inform decisions
• Excellent communication and stakeholder management skills across technical and non-technical audiences

Other Considerations

• Experience in EdTech or building products for learners, educators, or families
• Familiarity with search and discovery systems
• Background in marketplace technologies
• Experience at a fast-paced startup or high-growth company