Principal Software Engineer, AI (Web & Data)

TL;DR

Principal Software Engineer, AI (Web & Data) (AI/Web/Data): Leading the technical architecture and strategic integration of multi-modal AI into core identity infrastructure with an accent on AI-native web transformation and data orchestration. Focus on designing agentic pipelines, migrating legacy data flows to real-time event-driven architectures, and establishing standards for RAG and LLM orchestration.

Location: Hybrid in Toronto, Ontario, Canada

Salary: $175,000 — $192,500 CAD

Company

Okta is a leader in identity security, building neutral infrastructure that enables organizations to safely embrace AI through secure identity management.

What you will do

• Lead the roadmap for migrating legacy data pipelines to AI-native, real-time event-driven architectures using Apache Airflow, dbt, and Kafka.
• Architect the evolution of Headless CMS environments and modern frontend frameworks to enable AI-driven UI components and automated page assembly.
• Design and build autonomous agentic pipelines that bridge design systems, automated component development, and publishing workflows.
• Establish architectural standards for RAG, vector databases, and LLM orchestration across headless and omnichannel systems.
• Champion the use of AI-assisted coding tools such as Claude Code and Cursor to accelerate development cycles.

Requirements

• 8–10 years of experience in software engineering, specializing in SaaS platform architecture and distributed systems design.
• Hands-on experience with Apache Airflow, Kafka, and dbt for real-time AI applications.
• Proven expertise integrating LLMs into production web environments with a focus on agentic workflows.
• Deep understanding of headless CMS, composable, and event-driven architectural patterns.
• Experience with cloud-native technologies (AWS/GCP, Docker, Kubernetes) and data privacy frameworks.
• Must be based in or able to work hybrid from Toronto, Canada

Culture & Benefits

• Comprehensive health, dental, and vision insurance.
• RRSP with company match and healthcare spending accounts.
• Telemedicine and paid leave, including PTO and parental leave.
• Immersive in-person onboarding experience to accelerate team connection.
• Culture of innovation within a global community spanning over 20 offices.