Senior Staff Software Developer, Developer Productivity & AI Tooling

Join us in building the future of finance.

Our mission is to democratize finance for all. An estimated $124 trillion of assets will be inherited by younger generations in the next two decades. The largest transfer of wealth in human history. If you’re ready to be at the epicenter of this historic cultural and financial shift, keep reading.

About the team + role

We are building an elite team, applying frontier technologies to the world’s biggest financial problems. We’re looking for bold thinkers. Sharp problem-solvers. Builders who are wired to make an impact. the company isn’t a place for complacency, it’s where ambitious people do the best work of their careers. We’re a high-performing, fast-moving team with ethics at the center of everything we do. Expectations are high, and so are the rewards.

At the company, Developer Productivity is the backbone that enables every engineer to deliver exceptional software; faster, safer, and at scale. We design and build the systems, platforms, and experiences that make software development seamless and reliable across the company.

We believe infrastructure should be invisible when working perfectly, intuitive, resilient, and empowering. Our mission is to eliminate friction, enhance feedback loops, and drive developer productivity through operational excellence, intelligent automation, and world-class tooling.

We’re looking for a Senior Staff Software Developer to lead the evolution of our developer experience and AI-powered engineering ecosystem. In this role, you’ll operate as a technical leader and architect across the organization, shaping strategy, defining standards, and driving large-scale initiatives that improve developer velocity, system reliability, and engineering quality.

You’ll work at the intersection of developer tooling, platform infrastructure, and AI-assisted development, pioneering how the company engineers build, test, deploy, and operate software.

This role is based in our Toronto office(s), with in-person attendance expected at least 3 days per week.

At the company, we believe in the power of in-person work to accelerate progress, spark innovation, and strengthen community. Our office experience is intentional, energizing, and designed to fully support high-performing teams.

What you’ll do

Technical Leadership & Architecture

• Architect and build scalable systems that enable fast, reliable delivery of full-stack applications, with a strong focus on enhancing the overall developer experience
• Set technical direction and standards for developer infrastructure across build systems, CI/CD, testing, and local development
• Lead design reviews, operational readiness, and post-incident analysis for critical developer platforms
• Leveraging AI to power the next generation development workflow

Developer Experience & Productivity

• Identify and eliminate friction across the software development lifecycle
• Build and evolve developer tooling including CLIs, configuration systems, and local/remote development environments
• Drive improvements in build systems, test automation, and deployment workflows
• Champion best practices in code quality, observability, and operational excellence

AI Tooling & Intelligent Automation

• Lead adoption of AI-assisted development tools (e.g., Copilot, Claude) across engineering teams
• Design and implement agentic workflows for development and operations (e.g., automated code generation, incident triage, root cause analysis)
• Evaluate and integrate AI agents for anomaly detection, alert correlation, and automated remediation
• Establish best practices for safe, secure, and effective use of AI in software development

Cloud, Infrastructure & Platform Systems

• Design and operate services on AWS with strong attention to scalability, cost efficiency, and security
• Lead Kubernetes-based platform improvements, including developer workflows for containerized environments
• Drive Infrastructure as Code (Terraform) strategy and adoption across environments
• Build and optimize CI/CD pipelines (e.g., Harness, Jenkins, CircleCI) with a focus on reliability and speed

Reliability & Operations

• Own non-functional requirements including availability, scalability, latency, and security
• Ensure systems are observable through metrics, logs, and alertingLead incident response, postmortems, and continuous improvement efforts
• Reduce operational toil through automation and platform improvements

Cross-Functional Leadership

• Partner with Product, Platform, and SRE teams to align on long‑term technical strategy
• Lead large‑scale, cross‑functional initiatives spanning multiple engineering teams
• Mentor senior engineers and raise the technical bar across the organization
• Contribute to a strong engineering culture centered on ownership, quality, and continuous improvement

What you bring

• 10+ years of software engineering experience, including 3+ years operating at Staff or Senior Staff level
• Deep expertise in developer infrastructure (CI/CD, build systems, testing frameworks, dev environments, observability)
• Strong backend engineering skills with proficiency in Go, Python, or TypeScript/JavaScript
• Proven track record of leading complex, cross‑functional platform initiatives at scale
• Exceptional system design skills, with a focus on reliability, scalability, and performance

Infrastructure & Platform Experience

• Experience with cloud‑native technologies (Kubernetes, Docker, service discovery, distributed systems)
• Strong understanding of CI/CD systems (e.g., CircleCI, Jenkins, Harness) and release orchestration
• Experience building internal developer platforms, CLIs (preferably in Go), and productivity tooling
• Familiarity with Infrastructure as Code (Terraform) and cloud platforms like GCP

AI & Emerging Tooling

• Experience leveraging AI‑assisted development tools in production environments
• Interest or experience in applying AI to developer productivity, incident management, or automation
• Ability to evaluate and safely integrate AI systems into engineering workflows

Leadership & Influence

• Strong technical leadership with the ability to influence across teams and organizational boundaries
• Excellent communication skills, with experience driving alignment across engineering and product stakeholders
• Passion for developer experience and enabling other engineers to do their best work

What we offer

• Challenging, high‑impact work to grow your career
• Performance driven compensation with multipliers for outsized impact, bonus programs, and equity ownership
• Top tier benefits to fuel your work, including supplemental health insurance, ancillary insurance, and mental health support programs
• Lifestyle wallet - a highly flexible employer‑paid benefits spending account expenses beyond traditional benefits such as wellness, childcare, learning, and more.
• Time