Director of Engineering

This is a fully remote position, open to applicants in Canada.

📋 Description

• Lead, mentor, and develop a team of 5–10 engineers while actively engaging with architecture, system design, and technical direction.

• Directly contribute to the codebase as an individual contributor, enhancing development velocity and establishing high engineering standards.

• Spearhead engineering strategy and execution for a new, high-priority initiative.

• Collaborate cross-functionally with Product, Design, Data, Marketing, and Operations to provide an outstanding parent experience.

• Work closely with senior leadership to align on strategies, priorities, metrics, and long-term roadmap planning.

• Cultivate a culture of technical excellence, ownership, experimentation, and continuous improvement through mentorship and constructive feedback.

• Drive the adoption of AI-development principles and autonomous engineering workflows throughout the organization.

• Define and implement modern engineering practices that utilize AI to enhance developer speed and productivity, as well as product quality.

⛳️ Requirements

• Over 10 years of experience in software engineering.

• More than 5 years of engineering management experience leading medium-sized teams, with proven skills in performance management, career development, and personnel logistics.

• Familiarity with AI-native development methodologies and experience guiding teams through AI transformations.

• Strong proficiency in full-stack development: TypeScript, React, Node.js, GraphQL, and PostgreSQL.

• Experience balancing engineering leadership roles with hands-on coding and technical contributions.

• Demonstrated ability to lead multiple complex initiatives from planning through execution and delivery.

• Data-driven mindset with experience in leveraging experimentation, A/B testing, analytics, and metrics for decision-making.

• Capability to align engineering execution with broader business and product strategies.

• Experience in recruiting, hiring, and scaling high-performing engineering teams.

• Exceptional communication and stakeholder management skills across both 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 boasts a distributed team across the U.S. and Canada, along with a new office in San Francisco. Bay Area employees work in the office part of the week and receive commute-related benefits. Team members outside the Bay Area work fully remote, with support for home office setup, internet, and weekly meals to maintain connections regardless of location.

• Lifelong Learners: Annual budgets for professional development and DEI learning; funds for children to take Outschool classes.

• Community Impact: Outschool matches employee donations to eligible charities and supports Outschool.org’s nonprofit initiatives.