Principal Engineer

Overview

Guidepoint’s Engineering team thrives on problem-solving and creating happier users. As Guidepoint works to achieve its mission of making individuals, businesses, and the world smarter through personalized knowledge-sharing solutions, the engineering team is taking on challenges to improve our internal application architecture and create new products to optimize the seamless delivery of our services.

This position is hybrid in Toronto.

• Service Decomposition— Breaking apart a monolithic enterprise application into well‑bounded, independently deployable services. Define service boundaries, design APIs and contracts between them, and plan a phased migration strategy that keeps the business running while the architecture evolves.
• Data Migration— Leading the migration from a large, centralized multi‑tenant database to smaller, domain‑specific databases. Design the target schemas, build migration tooling, handle data integrity and validation, and coordinate cutover with minimal downtime.
• Developer Experience & Standards— Establish patterns, shared libraries, and CI/CD practices that make it easy for the rest of the engineering team to build on the new architecture with confidence.

• 8+ years of experience in backend or full‑stack engineering, with a demonstrated history of owning and delivering complex technical initiatives in enterprise environments.
• Architect mindset with IC ownership— Operate independently, make sound technical decisions, and drive projects from design through delivery without needing to be managed.
• Modernization expertise— Track record of migrating or re‑architecting legacy codebases into modern, maintainable systems without disrupting business continuity.
• Builder of new services— Design, build, and ship greenfield services end‑to‑end with production‑grade quality.
• Fast‑paced execution— Thrive in environments that value speed and iteration. Unblock yourself and move quickly without sacrificing quality.
• AI‑augmented engineering— Actively leverage AI‑assisted development tools (Cursor, etc.) to accelerate your workflow, and know how to validate and monitor AI‑generated output to ensure correctness and reliability.
• Backend & APIs— Solid Python proficiency with hands‑on FastAPI experience.
• Ability to design and build performance, well‑structured REST and Graph
  
  QL APIs.
• Databases— Deep experience with relational databases—Postgre
  
  SQL and/or SQL Server. Proficient in schema design, query optimization, and migrations.
• Messaging & events— Working knowledge of asynchronous messaging patterns using Rabbit
  
  MQ, Azure Service Bus, and/or Azure Event Hub.
• Infrastructure & CI/CD— Experience with containerized deployments on Kubernetes (K8s) and building/maintaining CI/CD pipelines (Azure Dev Ops, or similar).
• Frontend— Comfortable contributing to frontend codebases in React and Type Script. Can ship UI changes when needed.
• Observability— Hands‑on experience with Datadog or equivalent platforms for monitoring, logging, distributed tracing, and alerting in production systems.

Annual base salary range: $160,000–$180,000 CAD.

Eligible for an annual discretionary bonus based on performance.

• Paid Time Off
• Comprehensive benefits plan
• Company RRSP Match
• Development opportunities through the Linked In Learning platform

At Guidepoint, our success relies on the diversity of our employees, advisors, and client base, which allows us to create connections that offer a wealth of perspectives. We are committed to upholding policies that contribute to an equitable and welcoming environment for our community, regardless of background, identity, or experience.