Frontier AI Security Threat Hunter

Location

Remote (Canada)

Full time

Remote

Data & Engineering Security

• Base Salary CA $151.2K – CA $189K Offers Equity

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.

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.

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 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, App Sec, 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.

You’ll have substantial influence on the team’s roadmap through experimentation and R&D.

• Courageously Ambitious - they enthusiastically tackle big audacious goals.
• Deeply Human - they take responsibility for bringing the best out of themselves and others.
• Problem Solvers - they have the ability and resilience to tackle complex issues, find common patterns, design solutions for scale, and see them through.
• Enthusiastic Communicators - they capture and share learnings by default, and are always looking to implement suggestions for improvements and guardrails
• Embraces change and experimentation - treat campaigns and framework changes as experiments. Thoughtfully define hypotheses, evaluation criteria, and success metrics, then analyze outcomes and share results with the team to guide next iterations.

• Experience building AI- or automation-assisted offensive security tools.
• Experience (5+ years preferred) in…