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Sr PM – Cybersecurity
LinkedIn Recruiter Post
Sr PM - Cybersecurity 12mo contract in Toronto. Must have 10+ years PM experience, cyber security background, and Canadian banking experience.
About the role
- AI Security Researcher focusing on automated adversarial testing and R&D at Wealthsimple. Collaborate with a talented team to improve security measures against AI-enabled threats.
Responsibilities
- Design and build scaffolds to automate attacker/threat modeling, attack discovery and exploitation techniques at scale
- Identify promising attack surfaces and scenarios across Wealthsimple’s stack.
- Architect and tune agents, prompts, and toolchains that implement real attacker TTPs.
- Define success metrics and evaluation criteria for automations/ai so we can select and fine tune tooling and model use
- Design and iterate on multi-step agent strategies that combine observation, planning, action, and self-learning
- Improve effectiveness and automation coverage and reduce unproductive actions and loops
- Propose and validate new tools or environment features that enable richer or more realistic attacks.
- Research and design new AI-driven attack strategies and scenarios in anticipation of what adversaries might misuse LLMs to do in future, then help design detections and defensive measures
- Analyze AI behavior and results to discover systemic weaknesses and strengths and improve platform design / outputs and compensate for weaknesses.
- Compare different models, prompts, and tool sets on the same scenarios.
- Measure meaningful outcomes (bugs found, depth of compromise, time-to-finding, false-positive behaviour).
- Benchmark AI-driven testing against our other tooling and manual test results to understand return on investment and where to invest effort and expertise to best advantage
- Translate agent outputs into high-quality findings and systemic improvements.
- Identify high-confidence vulnerabilities and attack paths.
- Analyze findings to uncover recurring vulnerability types and control gaps, then help us fix them
- Understand how agents discovered issues and what that implies for our defences.
- Share learnings and help build guardrails, detections, systemic framework fixes, libraries, or new agents/experiments
Requirements
- 5+ years of experience in offensive security and/or vulnerability research
- Prior work blending automation with offensive security (e.g., custom tooling, fuzzer integrations).
- Strong technical skills in reading and reasoning about code, infrastructure, and designs.
- Experience building, evaluating, or using LLM- or agent-based systems in any domain.
- A strong curiosity about and openness to AI-augmented workflows:
- Comfortable iterating on prompts, tools, and agent behaviours.
- Pragmatic about what AI can and cannot do today.
- Working experience with large language models and how they work; for example, you may have written agent scaffolds
- Technical understanding of networks, endpoint, identity, cloud, encryption, data protection and application deployment stacks.
- Knowledge of standard penetration testing methodologies, including NIST SP 800-115.
- Preferred but not required:
- Published research papers on computer security, language modelling, offensive security tool benchmarking, or related topics; or given talks at Defcon, Blackhat, CCC, or other reputable venues
- Contributed to open-source projects in LLM- or security-related projects, especially those contributing to AI / LLM-specific guardrails and models
- Experience in financial services
- Data science and data pipeline development experience
- Familiarity with Ruby, React, GraphQL, AWS
- Some software or systems engineering experience
- Previous industry experience in Financial Services is preferred.
Benefits
- Top-tier health benefits and life insurance
- Long-term group savings with employer match, through Wealthsimple for Business
- 20 vacation days, 4 wellness days, and unlimited sick and mental health days per year
- 90 days away: work outside Canada for up to 90 days per year
- Employee resource groups, including Rainbow (2SLGBTQ), Women of WS, and Black at WS
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