Location
Remote (Canada)
Employment Type
Full time
Location Type
Remote
Department
Data & Engineering Security
Compensation
Base Salary CA$151.2 K – CA$189 K Offers Equity
Build something people love
Wealthsimple is Canada’s leading financial innovator. The company offers a full suite of simple, sophisticated financial products across managed investing, do-it-yourself trading, cryptocurrency, tax filing, spending and saving. Wealthsimple currently serves more than 4 million Canadians and holds over $125 billion in assets under administration. The company was founded in 2014 by a team of financial experts and technology entrepreneurs, and is headquartered in Toronto, Canada.
We're proud of what we've built — and we're just getting started. Read our Culture Manual and learn more about how we work.
About the team
We’re building a new AI-enabled adversarial testing capability whose mandate is straightforward but ambitious:



find all the ways Wealthsimple can be exploited before our AI-enabled adversaries do. This group combines penetration testing, secure code analysis, and attack simulation R&D; to continuously probe Wealthsimple’s systems using a combination of automation, autonomous AI agents, and human expertise. If you want to build an automated, end-to-end clearbox pentesting/red teaming platform, this is the team doing it!
You’ll join as an individual contributor on this team, reporting into the Manager, Application Security, working alongside a platform engineer, security researcher, and the application security team.
About the role
As a Frontier AI Security Penetration Tester, you’ll be a hybrid builder and breaker:
Design and run automation-driven attack campaigns against Wealthsimple’s products and infrastructure including activities like:
Designing realistic AI attack scenarios that

📌 Frontier Ai Security Threat Hunter (Winnipeg)
🏢 Wealthsimple
📍 Winnipeg