Staff Software Engineer

Core Responsibilities

Drive complex, high-impact engineering initiatives across personalized discovery, payments, reimbursement workflows, supply eligibility, and other related problem spaces.

Partner closely with Product, Design, Data, and Engineering leadership to align on roadmap priorities, technical tradeoffs, risks, and execution strategy.

Demonstrate AI-native development mindset leveraging fully agentic development workflows, while also contributing to establishing principles and best practices on AI development.

Mentor engineers and influence technical direction across teams through strong collaboration, communication, and domain expertise.

Participate in stand-ups, sprint planning, retros, production deployments, and on-call rotations.

Desired Experience & Skills

• 7+ years of software engineering experience
• Proficiency in full-stack development: TypeScript, React, Node.js, GraphQL, and PostgreSQL
• Proven track record of both demonstrated proficiency in AI-native development, and leading teams into it
• Demonstrated senior technical leadership: you've set direction, made architectural calls, and raised the bar for a team
• Strong communication and collaboration skills - you can translate technical complexity into clarity for engineers, product partners, and leadership alike

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

Compensation range for this role is $148,000 - $203,500 CAD annually.

Benefits & Culture

• Shared Financial Success: Competitive salaries, stock options, and retirement plans
• Health: Comprehensive medical, dental, vision, disability, and life insurance
• Wellness: Annual wellness stipend, access to coaching & therapy, and pet wellness plans
• PTO & Family Benefits: Generous PTO and family leave policies
• Hybrid & Remote-Friendly: Outschool has a distributed team across the U.S. and Canada and an 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 and internet 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

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.