We’re building a relationship-oriented bank for the contemporary world. As Director of Developer Experience at Simplii Technology, you'll play a pivotal role in shaping the future of engineering at Simplii Financial. You’ll build and lead a new team dedicated to making every engineer at Simplii faster, more consistent, and fully supported by AI.

Your mandate is to design and own our AI-native software development lifecycle, including our CI/CD platform, internal AI gateway, developer workflows, and the governance needed for a regulated bank. You’ll partner with senior leaders across engineering, security, risk, and compliance to ensure our investments in AI-assisted development are both ambitious and defensible. This is a founding leadership opportunity where your hands‑on technical judgement will set the tone for engineering culture and standards for years to come.

You'll have the flexibility to manage your work activities within a hybrid work arrangement where you'll spend 1-3 days per week on‑site, while other days will be remote.

Strategic

Leadership and Roadmap Ownership – Set the vision, strategy, and roadmap for Simplii’s AI-native software development lifecycle in collaboration with executive leadership.

Developer

Platform and Workflow Management – Design, implement, and continuously evolve the paved‑road developer workflow, ensuring every engineer follows a streamlined, AI‑assisted process. AI Tool Governance and Adoption – Lead the selection, adoption, measurement, and governance of AI tools used in engineering, including cost management and sunset processes. Team Building and Talent Development – Recruit, mentor, and grow a founding team of senior and staff‑level engineers,



scaling the function to approximately twelve members within eighteen months.

Stakeholder

Engagement and Operating Model Design – Define how the Developer Experience team collaborates with product engineering, security, risk, compliance, FinOps, and the data office.

Outcome

Ownership and Measurement – Own and report on key metrics such as cycle time, deployment frequency, change failure rate, developer satisfaction, AI‑tool adoption, and AI cost per active developer.

Regulatory

Compliance and Risk Partnership – Ensure all AI capabilities meet obligations under OSFI E-23, B-10, B-13, AIDA, and PIPEDA, partnering closely with Risk and the CISO’s office.

External

Representation – Represent Simplii Technology externally through speaking engagements, partner conversations, and industry forums to build engineering brand. You bring at least twelve years of software engineering experience, including five or more years leading engineering teams or organizations. You have deep, hands‑on technical experience.

Python, TypeScript, Go, and Java; Azure (primary), AWS (selective), Kubernetes, and Docker; coding‑assistant ecosystems, agent frameworks, evaluation harnesses, retrieval/RAG, and vector databases (such as pgvector and Pinecone); and source control and CI/CD using GitHub, GitHub Actions, and internal release platforms. You’ve built developer platforms at scale.



You have a proven track record of building or scaling developer experience, platform engineering, or productivity functions in complex environments.

You’re fluent in AI‑assisted SDLC. You understand coding assistants, agent workflows, evaluation, retrieval, and tool‑integration patterns at a depth sufficient to set architectural direction. You have experience recruiting and retaining senior and staff‑level engineers in competitive markets.

You understand the unique challenges and opportunities of building in a federally regulated financial institution and can balance speed with compliance. a competitive salary defined benefit pension plan* a vacation offering wellbeing support MomentMakers, our social, points‑based recognition program *All roles posted are opportunities we’re actively recruiting for, unless stated otherwise. You need to be legally eligible to work at the location(s) specified above and, where applicable, must have a valid work or study permit. We may ask you to complete an attribute-based assessment and other skills test (such as simulation, coding, French proficiency).

We use artificial intelligence tools during the recruitment process.

Skills Business Planning, Information Technology (IT) Projects, Leadership, Project Delivery, Project Management, Strategic Management, Technical Knowledge, Work Collaboratively At CIBC At CIBC, we are in business to help our clients, employees and shareholders achieve what is important to them. Working with CIBC makes you a part of a work environment committed to our clients, employees and communities - a place where you can excel. Every day, our 48,000 employees help our clients achieve their financial goals, because what matters to our clients, matters to us. #

📌 Director, Developer Experience, Simplii Technology (Toronto)
🏢 Canadian Imperial Bank of Commerce
📍 Toronto