Product Security Engineer

Ready to do the most impactful work of your career? At  the company , we are uncompromising on our mission to increase economic freedom. The bar is high, the environment is intense, and we like it that way. This isn't a place for complacency, it’s a place to be pushed past your perceived limits. If you're ready to build the future of finance alongside people who refuse to settle for "good enough," you belong here. The company is a remote-first, but not remote-only company. Expect to get together quarterly for intense in-person working sessions called “surges.”  Learn more about working at the company .

As an Offensive Security Engineer on the Application Security team within Security, you'll pioneer how the company uses frontier AI models to scale vulnerability discovery, red team AI systems, and automate security workflows. This role bridges traditional penetration testing with next-generation AI-augmented offensive security, directly accelerating our ability to protect products and customers. You'll own the development of AI-driven security tooling and collaborate across Vulnerability Management, Offensive Security, and Incident Response to fundamentally shift how we operate.

What you'll do

• Build, deploy, and maintain custom security scanners that leverage frontier models to detect vulnerabilities at scale across the company's product surface.

• Lead red teaming efforts against internal AI systems, including jailbreak testing, prompt injection analysis, and tool abuse simulation.

• Develop AI-driven automation for vulnerability triage, validation, and remediation workflows to accelerate the bug bounty and vulnerability response pipelines.

• Partner with engineering teams to prioritize, remediate, and verify fixes for critical vulnerabilities discovered through AI-augmented and manual testing.

• Mentor junior security engineers on integrating AI into offensive security workflows to scale team capabilities.

Required Skills and Experience

• 3+ years of experience in application security, penetration testing, or offensive security with demonstrated ability to build custom security tooling.

• Hands-on experience using LLMs or frontier models to automate security tasks, scale vulnerability research, or build security scanners.

• Demonstrated experience red teaming AI-based systems (prompt injection, jailbreak testing, tool abuse).

• Deep understanding of common vulnerability classes (OWASP Top 10, SANS Top 25) and proven track record identifying and exploiting them in production environments.

• Proficiency in at least one programming language (Python, Go, or similar) with experience writing production-grade security tooling.

• Utilizes generative AI responsibly, maintaining human oversight to deliver business-ready outputs and drive measurable improvements in workflow efficiency, cost, and quality.

Pay Transparency Notice: The target annual base salary for this position can range as detailed below. Total compensation may also include equity and bonus eligibility and benefits (including medical, dental, and vision).

Annual base salary range (excluding equity and bonus)

$154,000 — $154,000 CAD

• Application Limit: Candidates may submit a maximum of 3 applications within a 6-month period.

• Equal Opportunity Employer: the company is an Equal Opportunity Employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, disability, protected veteran status, or genetic information. Applicants with criminal histories will be considered consistent with applicable federal, state, and local laws.

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• Accommodations: If you are an individual with a disability who needs a reasonable accommodation, email us your request and contact info at accommodations[at]the company. Need screen reading technology? Click here to download a free compatible screen reader and view the tutorial .

• Data Privacy & Arbitration: By submitting your application, you agree to our Candidate Privacy Notice . US applicants: By submitting your application, you agree to Arbitration of Disputes .