Director, Developer Experience

CIBC•Toronto, ON

1d•Hybrid

About The Position

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.

Requirements

At least twelve years of software engineering experience, including five or more years leading engineering teams or organizations.
Deep, hands-on technical experience.
At least five years of experience working with all of the following: 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); tool-integration patterns including Model Context Protocol; observability and FinOps tools like Datadog, OpenTelemetry, Sentry, and cost-attribution tooling; and source control and CI/CD using GitHub, GitHub Actions, and internal release platforms.
Proven track record of building or scaling developer experience, platform engineering, or productivity functions in complex environments.
Understand coding assistants, agent workflows, evaluation, retrieval, and tool-integration patterns at a depth sufficient to set architectural direction.
Experience recruiting and retaining senior and staff-level engineers in competitive markets.
Understand the unique challenges and opportunities of building in a federally regulated financial institution and can balance speed with compliance.
Excellent communication skills, with written communication setting the standard for RFCs, governance documents, and strategic briefs.
Belief in doing what’s right for clients, colleagues, and the business, and acting with integrity in all that you do.

Responsibilities

Set the vision, strategy, and roadmap for Simplii’s AI-native software development lifecycle in collaboration with executive leadership.
Design, implement, and continuously evolve the paved-road developer workflow, ensuring every engineer follows a streamlined, AI-assisted process.
Lead the selection, adoption, measurement, and governance of AI tools used in engineering, including cost management and sunset processes.
Recruit, mentor, and grow a founding team of senior and staff-level engineers, scaling the function to approximately twelve members within eighteen months.
Define how the Developer Experience team collaborates with product engineering, security, risk, compliance, FinOps, and the data office.
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.
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.
Represent Simplii Technology externally through speaking engagements, partner conversations, and industry forums to build engineering brand.

Benefits

Competitive salary
Incentive pay
Banking benefits
Benefits program
Defined benefit pension plan
Employee share purchase plan
Vacation offering
Wellbeing support
MomentMakers, our social, points-based recognition program
Purpose Day; a paid day off dedicated for you to use to invest in your growth and development