Staff Systems Developer

Robinhood; Toronto; On-site; CAD 120,000 - 160,000; Full time

Job summary

A leading financial technology company in Toronto is seeking a Staff Systems Engineer to lead design and implementation of scalable systems supporting compliance and legal operations. The ideal candidate will have deep experience in regulated environments, strong cloud-native skills, and proficiency in automation languages. Responsibilities include technical ownership of core applications and leading M&A integrations. Join us in a mission to democratize finance while ensuring regulatory compliance.

Qualifications

• Proven experience as Staff or Principal engineer with application ecosystems.
• Deep work experience in compliance or highly regulated environments.
• Experience managing SaaS and on-premise applications.

Responsibilities

• Act as the technical owner for Compliance and Legal applications.
• Lead high-stakes technical integrations during M&A activity.
• Design and implement scalable systems to support compliance.

Skills

AWS or GCP experience

Python or Go proficiency

Cloud-native application design

Data protection principles understanding

Strong communication skills

Tools

Docker

Kubernetes

Global Relay or Smarsh

Job description

Overview

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

The Compliance and Legal Systems team’s mission is to leverage technology to ensure Robinhood complies with all applicable laws and regulations while protecting the firm. We focus on improving the effectiveness and efficiency of Compliance and Legal teams through scalable systems, improved workflows, automation, and strong controls.

As a Staff Systems Engineer, you’ll play a key leadership role across our Compliance and Legal technology portfolio. You’ll sit at the intersection of systems engineering, application development, and platform ownership—empowering the team with scalable solutions and deep technical guidance.

The role is located in the office location(s) listed on this job description which will align with our in-office working environment. Please connect with your recruiter for more information regarding our in-office philosophy and expectations.

What you’ll do

• Act as the technical owner for core Compliance and Legal applications, serving as the primary contact for M&A-related integrations, migrations, and system readiness.
• Lead high-stakes technical integrations during M&A activity. You will architect the strategy for data migrations and system consolidations, ensuring zero-loss transitions under tight regulatory windows.
• Design, implement, and operate scalable systems and workflows that support regulatory compliance, audit defensibility, and legal operations.
• Apply strong engineering judgment with a focus on security, data protection, reliability, and regulatory requirements.
• Lead the evaluation and implementation of best-in-class compliance and legal technology platforms.
• Champion the strategic adoption of AI and automation to drive infrastructure efficiency and operational excellence. Identify, prioritize, and lead initiatives that introduce AI-powered self-service, automation, and predictive capabilities, delivering measurable efficiency gains and cost savings.
• Design and build scalable automation tools and AI-enabled solutions, while setting technical direction, best practices, and standards across the organization.
• Architect and implement integrations using REST APIs to support seamless cross-system functionality.
• Collaborate closely with Compliance, Legal, Security, and external vendors, and influence senior stakeholders across geographies.
• Mentor fellow engineers and raise the bar for code quality, documentation, and operational excellence.
• Navigate ambiguity and drive clarity in roadmap priorities for Compliance and Legal systems.

What you bring

• Proven experience operating at a Staff or Principal engineering level, with a track record of designing, building, and scaling application ecosystems—not just administering SaaS vendor tools.
• Deep experience working in compliance, legal, or highly regulated environments, with a strong understanding of regulatory systems and audit requirements.
• Strong cloud-native experience with AWS or GCP, including hands-on work with serverless functions, containerization (Docker and Kubernetes), and secure data storage architectures.
• Significant domain experience with eDiscovery, data retention, and communications archiving platforms (such as Global Relay or Smarsh), as well as privacy technologies supporting GDPR and CCPA requirements.
• Practical understanding of data protection principles, including why controls exist and how they support regulatory and legal outcomes.
• Experience managing both SaaS-based and on-premise applications, including integrations, upgrades, and lifecycle management.
• Proficiency with programming or scripting languages such as Python or Go, particularly for automation, migrations, and systems integration.
• A strong operational discipline, demonstrated through idempotent automation, system observability, precise documentation, and structured change management.
• Experience leading enterprise-scale system migrations or M&A integrations, ideally within financial services or similarly regulated industries.
• Clear communication and stakeholder management skills, with the ability to balance immediate operational needs against long-term system design.

EEO and accommodations

Robinhood provides equal opportunity for all applicants, offers reasonable accommodations upon request, and complies with applicable equal employment and privacy laws.

AI Usage Disclosure: Robinhood uses artificial intelligence (AI) tools to support parts of our recruiting process. These tools enhance the efficiency and consistency of our hiring process; however, all hiring decisions are made by our hiring teams.