Staff Software Engineer

About Outschool: Outschool is an innovative EdTech marketplace leader on a mission to inspire kids to love learning. Reimagining traditional educational systems, Outschool offers highly flexible, interactive, and personalized online learning experiences as a supplement and alternative to conventional schooling. Launched in 2017, the platform connects over 1 million passionate young learners with a global community of educators and peers, driving more than $100M in annual bookings through hyper-scaled consumer marketplace technologies.

Position Overview

We are seeking a high-agency full-stack Staff Software Engineer to lead the architecture and product development of an ambitious, next-generation product platform. Driven by an agentic-first software engineering methodology, this platform will enable millions of families to seamlessly discover, navigate, and access public-funded educational resources via an AI-guided personalized planning journey. Operating as a senior technical leader across our distributed engineering squads, you will balance core hands-on stack programming with structural design calls, while establishing organizational principles on AI-native development workflows.

Key Responsibilities

• High-Impact Engineering Initiatives: Drive the development of complex, low-latency subsystems across personalized search discovery engines, processing gateways, compliance reimbursement workflows, and marketplace supply eligibility grids.
• Cross-Functional Roadmapping: Partner tightly with Product, Design, Data, and Engineering leadership to align on roadmap constraints, evaluate technical tradeoffs, and mitigate systemic execution risks.
• Agentic-First Engineering: Demonstrate and champion an AI-native development mindset, utilizing fully autonomous agentic development workflows while building internal tooling playbooks for the engineering organization.
• Technical Mentorship & Governance: Set long-term architectural directions, oversee structural code review gates, and mentor full-stack developers across multiple teams to continuously raise the engineering bar.
• Agile Execution Rhythms: Fully participate in agile sprint rituals, stand-ups, blameless postmortems, production code deployments, and critical production on-call rotations.

Required Skills & Qualifications

• 7+ years of verified professional experience in software engineering, with a definitive track record delivering high-quality commercial products within fast-paced startup or high-growth environments.
• Expert-level full-stack engineering proficiency developing within a modern open-source web ecosystem: TypeScript, React, Node.js, GraphQL, and PostgreSQL.
• Proven background of technical leadership, with verified experience making core architectural calls and setting systems direction across multiple engineering teams.
• Demonstrated proficiency navigating AI-native coding setups and a passion for mentoring developer squads into agentic workflow models.
• Outstanding written, verbal, and visual communication skills, capable of translating complex backend code dependencies into clarity for engineering and leadership stakeholders alike.
• Location Context: 100% remote-first workspace flexibility open to qualified full-stack professionals residing anywhere within the United States or Canada.

Preferred Strategic Indicators (Nice to Have)

• Direct production engineering exposure inside the EdTech sector, or a background building consumer tools tailored for learners, educators, and families.
• Familiarity designing large-scale search ranking profiles, dynamic indexing arrays, or multi-tenant transactional marketplace technologies.
• Experience navigating automated applicant tracking integrations, specifically leveraging Covey scout data layers.

What We Offer

• Tiered Base Salary Ranges: Canada locations: $164,000 – $205,000 CAD per annum. United States locations calibrated by Tiered Cost of Labor zones: Tier 1 (SF Bay Area, NYC): $158,950 – $198,000 USD; Tier 2 (Other CA cities, Seattle, Boston, Austin, Denver, Portland metros): $135,108 – $168,300 USD; Tier 3 (All other U.S. cities): $118,800 – $148,500 USD.
• Competitive startup equity options paired with robust regional retirement savings programs.
• Premium comprehensive medical, dental, and vision health coverage plans, featuring fertility/family planning and access to ModernHealth mental coaching networks.
• Generous Paid Time Off (PTO) frameworks combined with inclusive corporate paid family leave programs.
• Home workstation setup stipends alongside ongoing data expenses coverage and weekly remote meal allowances.
• Dedicated annual professional development budgets, including special allocations for children to take free Outschool classes.