Join us in building the future of finance. Our mission is to democratize finance for all. An estimated $124 trillion of assets will be inherited by younger generations in the next two decades. If you’re ready to be at the epicenter of this historic cultural and financial shift, keep reading.

We are building an elite team, applying frontier technologies to the world’s biggest financial problems. Builders who are wired to make an impact. Through red teaming and adversarial simulations, the team evaluates security controls, uncovers vulnerabilities, and helps continuously strengthen Robinhood’s overall security posture in close partnership with Detection & Response, Physical Security, and Engineering.

As a Staff Offensive Security Engineer, you will take a hands‑on role in designing and executing stealthy adversarial simulations to validate assumptions and uncover gaps in detection and response. You’ll leverage threat modeling, penetration testing, and research‑driven techniques to emulate sophisticated attackers, while collaborating cross‑functionally to improve defenses and shape more secure systems. This role is based in our Toronto, Canada office(s), with in‑person attendance expected at least 3 days per week.

At Robinhood, we believe in the power of in‑person work to accelerate progress, spark innovation, and strengthen community. Our office experience is intentional, energizing, and designed to fully support high‑performing teams. Plan and execute red team operations, adversarial simulations, and penetration tests across applications, infrastructure, networks, offices, and internal processes.

Perform threat modeling for new and existing services, clearly articulating security risks and tradeoffs to engineering and risk stakeholders. Conduct vulnerability research, exploit development, and testing using both custom tooling and public proof‑of‑concept techniques. Write and maintain tooling to automate and scale offensive security assessments. 8+ years of hands‑on experience in red teaming, offensive security,



or penetration testing. ~ Demonstrated experience mentoring or guiding other security engineers. ~ Experience testing modern environments, including cloud platforms (AWS, GCP), containerized systems (Docker, Kubernetes), CI pipelines, and identity systems. ~ Working knowledge of defensive security tools such as IDS/IPS, EDR, packet capture, and network monitoring, including common evasion techniques. ~ Proficiency in Python, Go, or JavaScript for exploit development, tooling, or automation. ~ Clear written and verbal communication skills, with the ability to explain technical findings to both engineers and senior leaders. ~ Bonus Points Prior experience serving as a technical lead on security initiatives.

Performance driven compensation with multipliers for outsized impact, bonus programs, and equity ownership Top tier perks to fuel your work, including supplemental health insurance, ancillary insurance, and mental health support programs Lifestyle wallet - a highly flexible employer‑paid benefits spending account expenses beyond traditional benefits such as wellness, childcare, learning, and more. Time off to recharge including company holidays, paid time off, sick time, paid volunteer time off, parental leave, and more! Exceptional office experience with catered meals, events, and comfortable workspaces.

Monthly commuter stipend to help offset in‑office commuting costs AI Usage Disclosure: Robinhood uses artificial intelligence (AI) tools to support parts of our recruiting process. These tools enhance the efficiency and consistency of our hiring process; In addition to the base pay range listed below, this role is also eligible for bonus opportunities + equity + benefits. 191,250—$225,000 CAD Base pay for the successful applicant will depend on a variety of job‑related factors, which may include education, training, experience, location, business needs, or market demands. Inclusion is built into how we hire and work—welcoming different backgrounds, perspectives, and experiences so everyone can do their best.

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📌 Staff Offensive Security Engineer (Toronto)
🏢 Robinhood
📍 Toronto