Director of Engineering

🕒 May 27

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Outschool

WebsiteLinkedInAll Job Openings

51 - 200 employees

Founded 2015

📚 Education

👥 B2C

🛍️ eCommerce

💰 $110M Series D on 2021-10

Education • B2C • eCommerce

Outschool is an online learning platform offering live video chat classes taught by expert educators and tutors. It provides a wide range of classes for learners aged 3 to 18, covering subjects such as languages, math, coding, music, and art, among others. Outschool offers flexible learning options, including group and one-on-one classes, personalized tutoring, and afterschool activities, nurturing neurodiversity and accommodating various learning preferences. The platform connects students with teachers and fellow learners worldwide, enhancing their educational experience and rekindling their love of learning.

📋 Description

• 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

🎯 Requirements

• 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 delivery • Data-driven mindset with experience leveraging experimentation, A/B testing, analytics, and metrics to inform decisions • Ability to align engineering execution with broader business and product strategy • Experience recruiting, hiring, and scaling high-performing engineering teams • Excellent communication and stakeholder management skills across technical and non-technical audiences.

🏖️ 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.