Director of Engineering New Remote (U.S. & Canada)

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, connecting learners with a global community of teachers and peers through our online platform.

The Role

We’re hiring a Director of Engineering to lead a strong product engineering team developing Outschool’s mission‑critical products, including an AI‑powered platform that transforms how families navigate the complex world of alternative education. This highly impactful leadership role combines technical strategy, people leadership, and hands‑on development. The ideal candidate will shape Outschool’s most critical products, our engineering culture, and AI‑native development models 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 establishing 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, 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 guide 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.

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.

Compensation

Outschool recruits across the US and Canada, setting employee salaries to reflect local compensation and cost of living.

This role is available in Canada: the salary range is $220,000–$275,000 CAD annually.

US Pay Zones:

• Tier 1: San Francisco Bay Area and New York City
• Tier 2: All California excluding San Francisco Bay Area, Seattle Metro, Boston Metro, Chicago Metro, Denver Metro, Austin Metro, Portland Metro
• Tier 3: All other cities and states

Benefits & Culture

• Competitive salaries, stock options, and retirement plans.
• Comprehensive medical, dental, vision, disability, and life insurance, plus fertility/family planning coverage and access to ModernHealth coaching & therapy.
• Generous PTO and family leave policies.
• Hybrid & remote‑friendly: distributed team across the U.S. and Canada; Bay Area employees work in‑office part of the week with commute‑related benefits; remote employees receive support for home office setup, internet, and weekly meals.
• Annual budgets for professional development, DEI learning, and for children to take Outschool classes.
• 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.

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