Frontier AI Security Researcher

Wealthsimple Technologies • ,

2d • CA$151,200 - CA$189,000 • Hybrid

About The Position

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 one or more threat hunters/adversarial simulation/pentesters, a platform engineer, and the application security team.

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.

Nice To Haves

• 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.

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
• Help shape the team’s direction through research, proposals, benchmarking, and improved design/implementation.

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

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed