Director, Developer Experience, Simplii Technology

Simplii Financial; Toronto; Hybrid; CAD 180,000 - 240,000; Full time

Benefits offered by this job

Competitive salary and incentive pay

Banking benefits

Benefits program

Defined benefit pension plan

Employee share purchase plan

Vacation offering

Wellbeing support

MomentMakers

Job summary

Simplii Financial seeks an experienced Director of Developer Experience to build and lead a new AI-enabled SDLC team. You will shape the developer experience, drive platform strategy, and partner with engineering, security, risk, and compliance to ensure scalable, compliant AI-driven development.

You will oversee hiring, architecture, and governance, balancing speed with regulatory requirements while delivering measurable improvements in deployment efficiency and engineer satisfaction.

Qualifications

• Senior engineering leadership with 12+ years in software, including 5+ years leading teams.
• Deep hands-on technical experience across modern cloud stacks and AI-enabled SDLC.
• Proven ability to build and scale developer platforms in complex environments.

Responsibilities

• Set vision, strategy, and roadmap for AI-native SDLC and developer experience.
• Design, implement, and evolve the paved-road developer workflow with AI support.
• Lead AI tool governance, adoption, cost management, and sunset processes.
• Recruit, mentor, and grow a founding team of engineers toward ~12 people in 18 months.
• Define collaboration models with product engineering, security, risk, compliance, FinOps, and data office.
• Own metrics like cycle time, deployment frequency, change failure rate, and developer satisfaction.
• Ensure AI capabilities meet OSFI, B–10, B–13, AIDA, and PIPEDA obligations with Risk and CISO.

Skills

Leadership

Strategic vision

AI/SDLC

Python

TypeScript

Go

Java

Azure

Kubernetes

Docker

CI/CD

GitHub Actions

Datadog

OpenTelemetry

Sentry

Tools

GitHub

GitHub Actions

Model Context Protocol

Datadog

OpenTelemetry

Sentry

pgvector

Pinecone

Job description

We’re building a relationship-oriented bank for the modern world. We need talented, passionate professionals who are dedicated to doing what’s right for our clients.

At CIBC, we embrace your strengths and your ambitions, so you are empowered at work. Our team members have what they need to make a meaningful impact and are truly valued for who they are and what they contribute.

To learn more about CIBC, please visit CIBC.com

What You'll Be Doing

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.

At CIBC we enable the work environment most optimal for you to thrive in your role. 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.

How You'll Succeed

• 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.

Who You Are

• You’re an experienced engineering leader. 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. You bring 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.
• 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’re skilled in talent acquisition and retention. You have experience recruiting and retaining senior and staff‑level engineers in competitive markets.
• You thrive in regulated environments. You understand the unique challenges and opportunities of building in a federally regulated financial institution and can balance speed with compliance.
• You’re an excellent communicator. Your written communication sets the standard for RFCs, governance documents, and strategic briefs.
• Values matter to you. You believe in doing what’s right for clients, colleagues, and the business, and you act with integrity in all that you do.

What CIBC Offers

At CIBC, your goals are a priority. We start with your strengths and ambitions as an employee and strive to create opportunities to tap into your potential. We aspire to give you a career, rather than just a paycheck.

• We work to recognize you in meaningful, personalized ways including a competitive salary, incentive pay, banking benefits, a benefits program*, defined benefit pension plan*, an employee share purchase plan, a vacation offering, wellbeing support, and MomentMakers, our social, points‑based recognition program.
• Our spaces and technological toolkit will make it simple to bring together great minds to create innovative solutions that make a difference for our clients.
• We cultivate a culture where you can express your ambition through initiatives like Purpose Day; a paid day off dedicated for you to use to invest in your growth and development.
• Subject to plan and program terms and conditions

What You Need To Know

• CIBC is committed to creating an inclusive environment where all team members and clients feel like they belong. We seek applicants with a wide range of abilities and we provide an accessible candidate experience. If you need accommodation, please contact [e-mail]
• CIBC is committed to clarity in our hiring process. 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. Our goal for the application process is to get to know more about you, all that you have to offer, and give you the opportunity to learn more about us.

Job Location

Toronto-81 Bay, 16th Floor

Employment Type

Regular

Weekly Hours

37.5

Skills

Business Planning, Information Technology (IT) Projects, Leadership, Project Delivery, Project Management, Strategic Management, Technical Knowledge, Work Collaboratively