Wealthsimple
Financial Services
FrontierAISecurityThreatHunter
Neural analysis suggests this role is
optimal for Mid+ candidates.
“Frontier AI Security Threat Hunter at Wealthsimple. Skills: AI Security, Adversarial testing, Automated pentesting, Red teaming. Design automation-driven attack campaigns. Run automation-driven attack campaigns”
What You'll Achieve.
Find all ways Wealthsimple can be exploited; Automate replay of attack paths; Automate workflows; Turn noisy outputs into actionable findings; Make automated testing routine; Make AI adversarial testing routine
Industry & Context.
Problem solving; Resilience; Design solutions for scale; Root cause analysis; Debugging; Troubleshooting
What They're Looking For.
Must Have
5+ years offensive security testing, Reading and reasoning about code, Understanding modern cloud-native architectures, Technical understanding of networks, Technical understanding of endpoint, Technical understanding of identity, Technical understanding of cloud, Technical understanding of encryption, Technical understanding of data protection, Technical understanding of application deployment stacks, Knowledge of standard penetration testing methodologies, Familiarity with LLM- or agent-based systems
Nice to Have
AWS testing experience, Financial Services industry experience
What You'll Do.
Design automation-driven attack campaigns
Run automation-driven attack campaigns
Design realistic AI attack scenarios
Account for attacker goals
Account for initial access assumptions
Account for constraints
Define success criteria
Define clear boundaries for safety
Account for Wealthsimple-specific risks
Account for design flaws
Account for trust boundaries
Account for risk tolerance
Perform vulnerability probing
Perform impact analysis
Perform post-exploitation
Shape automated testing pipeline
Improve automated testing pipeline
Run automated workflows
Turn noisy outputs into actionable findings
Improve scenario modeling
Improve workflow modeling
Automate replay of attack paths
Unlock richer attack behavior
Learn in-house tooling
Find more vulnerabilities
Work across the stack
Make automated testing routine
Make AI adversarial testing routine
Review AI-generated findings
Separate high-impact vulnerabilities from noise
Separate false positives
Enhance proofs-of-concept
Create clear steps for engineering teams
Create reproducible steps for engineering teams
Create new automations
Verify fixes address root cause
Influence team's roadmap
Experiment with new capabilities
How You'll Work.
Team & Collaboration
Platform engineer; Security researcher; Application security team; Platform engineers; AppSec; Other security teams; Engineering teams
Communication Scope
Share learnings; Implement suggestions; Share results
Process & Methodology
Roadmap planning, Experimentation, Hypotheses definition, Evaluation criteria definition, Success metrics definition, Outcome analysis
Full Job Description
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 https://www.wealthsimple.com/en-ca/culture and learn more about how we work https://www.wealthsimple.com/en-ca/careers. ABOUT THE TEAM We’re building a new AI-enabled adversarial testing capability whose mandate is simple 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 account for: - Attacker goals, initial access assumptions, and constraints. - Success criteria and clear boundaries for safety. - Wealthsimple-specific risks, design flaws, trust boundaries, and risk tolerance - Use and evolve our AI agents and tooling to: - Perform reco
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