Who you are

- 15+ years of software engineering experience, with at least 5+ years in engineering leadership, including explicitly managing managers and leading multiple teams

- High AI Fluency: Proven experience architecting systems that support AI features (LLMs, RAG, tool calling) and a track record of driving AI-assisted development tools (AI SDLC) across engineering teams
- An executive track record of successfully guiding massive monolith-to-modular migrations and decoupling shared database schemas in high-traffic, business-critical environments

- Deep strategic understanding of Application Security principles, Identity/Access Management (OAuth 2.0, OIDC), and modern API traffic management

- Strong technical fluency in Python and FastAPI ecosystems, with the ability to guide Staff-level engineers through complex architectural decisions involving both modern APIs and legacy applications

- Exceptional executive communication skills, with the ability to translate complex technical, security, and AI trade-offs into business value

What the job involves

- As the Director, Engineering you will lead the vision and execution for the foundational systems that power our entire engineering organization

- Your mandate spans four critical pillars: architecting the modularization of our core Python/FastAPI monolith, accelerating our transition to an AI-native engineering culture, empowering product teams with tools to build AI-enabled features, and establishing a robust Application Security (AppSec) posture

- You will manage a group of engineering managers and staff engineers

- You will act as a strategic multiplier for the company, treating our internal platform as a top-tier product

- Your ultimate goal is to create secure,



high-velocity "paved paths" that make our product teams incredibly fast, while systematically reducing technical debt and security risks

- Direct the Monolith Evolution: Own the multi-year technical strategy to safely decouple our legacy Python/Jinja monolith into a contemporary, modular FastAPI architecture using Domain-Driven Design and zero-downtime database migration tactics

- Drive the AI-Native SDLC: Champion the rollout and adoption of AI-assisted coding tools and AI-augmented workflows across the entire engineering organization, systematically measuring and improving developer productivity

- Enable AI Feature Development: Treat the internal platform as a product. Guide the development of intuitive SDKs, data pipelines, and internal tools that reduce cognitive load and allow product engineers to easily integrate LLMs and build AI-powered features

- Lead Application Security (AppSec): Champion a "shift-left" security culture. Embed secure coding practices, automated vulnerability scanning, and threat modeling directly into developer workflows, ensuring our core platform is resilient against modern threats

- Oversee Core Shared Services: Drive the scale, security, and reliability of enterprise-critical systems, including Identity (AuthN/AuthZ, OAuth2, RBAC), Audit Logs, and high-throughput API & MCP Gateways

- Navigate Org-Wide Boundaries: Negotiate complex refactoring timelines with Product leaders and collaborate seamlessly with other Engineering teams and DevOps to align our platform capabilities with infrastructure

- Build a World-Class Organization: Recruit, mentor, and grow a high-performing organization of engineering managers and staff/principal engineers, fostering a culture of architectural pragmatism and deep developer empathy

📌 Director of Engineering (Canada)
🏢 Juniper Square
📍 Canada