Director of Engineering
About The Position
Outschool is seeking a Director of Engineering to lead a strong product engineering team focused on developing mission-critical products. This includes a new AI-powered platform designed to transform how families navigate alternative education and reimbursement processes. The role involves developing new 0-to-1 products from scratch and scaling existing user journeys on Outschool’s marketplace. It's a leadership position that blends technical strategy, people management, and hands-on development. The ideal candidate will influence Outschool’s products, engineering culture, talent development, and AI-native development models, ultimately impacting millions of families.
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
Nice To Haves
- 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
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.
Benefits
- Competitive salaries
- Stock options
- Retirement plans
- Comprehensive medical, dental, vision, disability, and life insurance
- Fertility/family planning coverage
- Access to ModernHealth coaching & therapy
- Generous PTO
- Family leave policies
- Support for expensable home office setup, internet, and weekly meals for remote employees
- Annual budgets for professional development and DEI learning
- Budgets for children to take Outschool classes
- Donation matching to eligible charities
- Support for Outschool.org’s nonprofit programs
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What This Job Offers
Job Type
Full-time
Career Level
Director
Education Level
No Education Listed
