Frontier AI Security Penetration Tester at Wealthsimple developing automation-driven attack campaigns. Collaborate with engineers to enhance automated testing pipelines and AI-driven security measures.
Responsibilities
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 recon, vulnerability probing, confirmation, impact analysis, exploitation, and post-exploitation in safe environments.
Help shape and improve the automated testing pipeline: how we model assets, orchestrate agents, run automated workflows, and turn noisy outputs into actionable findings. You’ll work closely with a platform engineer and a researcher to improve how scenarios and workflows are modeled and automated so we can automate the replay of promising attack paths.
Build and improve AI agents and tooling
Propose and validate new tools or capabilities that unlock richer attack behavior
Learn to use our native and in-house tooling to find more
Work across the stack with platform engineers, AppSec, and other security teams to make automated and AI adversarial testing a routine, high-signal part of our SDLC. This includes:
- Reviewing AI-generated findings to separate high-impact vulnerabilities from noise and false positives.
- Enhance proofs-of-concept into clear, reproducible steps for engineering teams and new automations
- Support remediation by pairing with engineers when needed and verifying that fixes address the root cause.
Requirements
Experience (5+ years preferred) in offensive security testing domains like penetration testing, red teaming, threat hunting, or attack simulations in complex environments with a proven history of working cross-functionally with high functioning teams.
Strong technical skills in:
- Reading and reasoning about code and system designs.
- Understanding modern cloud-native architectures (preferably AWS).
- 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.
- Familiarity with LLM- or agent-based systems (tool use/function calling, prompt design).
Comfort working with novel tools and ambiguity:
- You’re already experimenting with AI agents and have always had a scale and automation-first mindset to testing and discovering new vulnerabilities.
- You can turn open-ended problems into small, testable steps.
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
Market Intelligence Analyst in a hybrid role at Egg Farmers of Canada. Responsible for research, analysis, and market expertise for Canadian egg markets.
Senior Technical and Financial Crime Intelligence Analyst transforming data into actionable insights for bank investigations. Driving data - driven decisions using advanced analytics within regulatory frameworks.
Market Intelligence Analyst at Egg Farmers of Canada conducting market research and analysis. Responsible for data collection, market expertise, and program execution for egg production and markets.
Senior Market Intelligence & Research Analyst at BeInCrypto developing institutional - grade research products to support B2B growth. Collaborating with teams to create high - value reports for institutional audiences.
Senior Staff Threat Intelligence Researcher at Lookout Inc identifying and investigating mobile threats. Working with a team to enhance security efforts using diverse technical tools and methodologies.
Commercial Intelligence Analyst supporting MedSpa Partners' growth strategies. Analyzing patient and marketing data to inform decision - making and identify performance opportunities.
Fraud Intelligence Analyst examining and disrupting fraud patterns at Airbnb. Collaboratively engaging with teams to enhance platform integrity and safety.
Decision Intelligence Analyst responsible for evaluating decision outputs and improving AI reasoning quality at Rwazi. Safeguarding the integrity of decision - making processes with structured analysis.
Market Intelligence Analyst at Cummins focusing on market reports and intelligence for informed strategies. Collaborating across functions to enhance business decision - making with data insights.