Staff Offensive Security Engineer

Robinhood; Toronto; On-site; CAD 191,000 - 225,000; Full time

Benefits offered by this job

Equity ownership

Bonuses

Benefits package

Commuter stipend

Job summary

Robinhood in Toronto, Canada seeks a Staff Offensive Security Engineer to design and execute stealthy adversarial simulations, validate assumptions, and uncover gaps in detection and response. You will leverage threat modeling, pentesting, and research-driven techniques to strengthen defenses and build more secure systems.

You will mentor teammates, document findings, and drive remediation with cross-functional partners.

Qualifications

• 8+ years of hands-on experience in red teaming, offensive security, or penetration testing.
• Demonstrated experience mentoring or guiding other security engineers.
• Strong understanding of threat modeling methodologies and the MITRE ATT&CK framework.
• 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.
• Experience collaborating with distributed teams and documenting work through tools such as Slack, Jira, GitHub, and email.

Responsibilities

• 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.
• Partner with detection and response teams to simulate realistic attack scenarios and evaluate monitoring and incident response readiness.
• Write and maintain tooling to automate and scale offensive security assessments.
• Serve as a subject matter expert by documenting findings, recommending remediation strategies, and supporting teams through fixes.
• Mentor teammates and contribute to shared knowledge through internal documentation, presentations, and external talks or blog posts.

Skills

Red teaming

Mentoring

Threat modeling

MITRE ATT&CK

AWS/GCP

Docker/Kubernetes

CI pipelines

Identity systems

Python/Go/JS

Communication

Distributed teams

Documentation tools

Tools

Slack

Jira

GitHub

Email

IDS/IPS

EDR

Packet capture

Network monitoring

Job description

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. The largest transfer of wealth in human history. If you’re ready to be at the epicenter of this historic cultural and financial shift, keep reading.

About the team + role

We are building an elite team, applying frontier technologies to the world’s biggest financial problems. We’re looking for bold thinkers. Sharp problem-solvers. Builders who are wired to make an impact. Robinhood isn’t a place for complacency, it’s where ambitious people do the best work of their careers. We’re a high-performing, fast-moving team with ethics at the center of everything we do. Expectations are high, and so are the rewards.

The Red Team team’s mission is to proactively identify and simulate real-world threats against Robinhood’s platforms, properties, and people. 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.

What You’ll Do

• 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.
• Partner with detection and response teams to simulate realistic attack scenarios and evaluate monitoring and incident response readiness.
• Write and maintain tooling to automate and scale offensive security assessments.
• Serve as a subject matter expert by documenting findings, recommending remediation strategies, and supporting teams through fixes.
• Mentor teammates and contribute to shared knowledge through internal documentation, presentations, and external talks or blog posts.

What You Bring

• 8+ years of hands‑on experience in red teaming, offensive security, or penetration testing.
• Demonstrated experience mentoring or guiding other security engineers.
• Strong understanding of threat modeling methodologies and the MITRE ATT&CK framework.
• 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.
• Experience collaborating with distributed teams and documenting work through tools such as Slack, Jira, GitHub, and email.

Bonus Points

• Experience working in financial technology or regulated environments.
• Prior experience serving as a technical lead on security initiatives.

What We Offer

• Challenging, high‑impact work to grow your career
• Performance driven compensation with multipliers for outsized impact, bonus programs, and equity ownership
• Top tier benefits 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

Our team is committed to providing an inclusive and welcoming interview experience for all candidates.

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; however, all hiring decisions are made by our hiring teams.

Vacancy Notice: This job posting represents an existing vacancy that we are actively seeking to fill.

In addition to the base pay range listed below, this role is also eligible for bonus opportunities + equity + benefits.

Base Pay Range

Toronto, ON

$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. The expected base pay range for this role is based on the location where the work will be performed.

Robinhood provides equal opportunity for all applicants, offers reasonable accommodations upon request, and complies with applicable equal employment and privacy laws. Inclusion is built into how we hire and work—welcoming different backgrounds, perspectives, and experiences so everyone can do their best. Please review the Privacy Policy for your country of application.