Director of Engineering

About Outschool

Outschool’s mission is to inspire kids to love learning. The company offers flexible and engaging learning experiences as a supplement and alternative to traditional education.

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 while obtaining reimbursements through public‐funding programs. This role will develop 0‐to‐1 products and scale user journeys on the existing marketplace. It is a highly impactful leadership role that 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
• Familiarity with AI‐native development paradigms and experience taking 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

Canada: $220,000 – $275,000 CAD annually.

US Pay Zones: Tier 1: $260,000 – $325,000; Tier 2: $221,000 – $276,250; Tier 3: $195,000 – $243,750.

Benefits & Culture

• Competitive salaries, stock options, and retirement plans
• Health & wellness: comprehensive medical, dental, vision, disability, life insurance, fertility/family planning coverage, and ModernHealth coaching & therapy
• Generous PTO and family leave policies
• Hybrid & remote‐friendly work environment with support for home office setup, internet, and meals
• Annual budgets for professional development and DEI learning; budgets for children to take Outschool classes
• Outschool matches employee donations to eligible charities and supports Outschool.org’s nonprofit programs

Equal Opportunity Employer & Accessibility

Outschool is an equal‐opportunity employer. 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.

Legal Notices

Full‐time employees must be a citizen or legal resident of the U.S. or Canada and reside in the U.S. or Canada, unless specifically indicated otherwise. Once you submit your application, Outschool will process your personal data to evaluate your candidacy for employment. If you are not hired, your application will be retained for one year in case there is another suitable role. You may opt out at any time. For more detailed information, see Outschool Employee/Applicant Privacy Notice.