Senior Offensive Security Engineer

Robinhood; Toronto; On-site; CAD 136,000 - 160,000; Full time

Job summary

A leading financial technology company in Toronto is hiring an Offensive Security Engineer to lead Red Team initiatives. The role emphasizes threat modeling, penetration testing, and mentoring team members. Ideal candidates have over 5 years of Red Team experience and excellent communication skills. This dynamic position supports security across the organization and offers a competitive salary plus bonuses and benefits.

Benefits

Bonus opportunities

Equity options

Comprehensive benefits package

Qualifications

• 5+ years of experience on Red Team.
• Ability to mentor and guide team members.
• Passion for tackling security assumptions and issues.

Responsibilities

• Evangelize the Offensive Security Team’s Findings with stakeholders.
• Utilize threat modeling to identify threats.
• Perform penetration testing and code reviews.

Skills

Red Team experience

Mentoring capabilities

Excellent communication skills

Knowledge of network protocols

Experience with MacOS and Linux

Comfortable with Python, Go, and JavaScript

Tools

CI/CD tools

Kubernetes

Docker

AWS

GCP

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.

Robinhood is looking for an Offensive Security Engineer who is passionate about Red Teaming, Adversarial Simulation, and breaking / fixing systems, to join the Red Team.

The Red Team is a core pillar of the Offensive Security team and situated within the Safety & Productivity Engineering organization. The Red Team works with teams across Robinhood to ensure our products, services, and processes are secure through threat modeling, penetration testing, adversarial simulations, and red teaming.

Here are some examples of things our team does frequently that you’ll be heavily involved with:

• Red Teaming to validate assumptions, facilitate decisions, and improve our ability to detect and respond to incidents.
• Perform threat modeling against critical and new services. Articulate the actual security risk to risk working groups.
• Penetration testing our critical infrastructure, production applications, networks, offices, and processes.
• Sparring with Detection and Response and other stakeholders via Adversarial Simulations to prepare for incidents.
• Partnering with the physical security team to conduct assessments of Robinhood properties.
• Serving as a technical advocate and Subject Matter Expert for privacy and security decisions, designs, and discussions.
• Driving innovative ideas to implementation as the company evolves and grows.
• Conduct vulnerability research to understand latest TTPs, exploits, and forward looking capabilities.
• Leaving things better than you found them by partnering to fix the issues and not just finding broken things.

As an Offensive Security Engineer, you will work across multiple domains, partner with key teams across Robinhood, and help build an even more resilient and secure product for our customers.

The role is located in the office location(s) listed on this job description which will align with our in-office working environment. Please connect with your recruiter for more information regarding our in-office philosophy and expectations.

What you’ll do

• Evangelize the Offensive Security Team’s Findings and Projects with stakeholders throughout the company and collaborate with other teams to create solutions that balance security with other priorities.
• Mentor and provide guidance to the members of the Offensive Security team.
• Utilize threat modeling to identify threats and shape Red Team priorities and exercises.
• Plan and execute long term, broadly scoped, black box Red Team exercises utilizing vulnerability research, exploit development, and utilizing public proof of concept code.
• Perform penetration testing, code reviews, and design/architecture reviews.
• Write tooling to assist with and automate Red Team assessments.
• Plan and participate in Adversarial Simulation exercises with various security teams.
• Lead Security Incidents when Pentest or Red Team findings require them.
• Publish blog posts and present talks at security conferences.

What you bring

• 5+ years of Red Team experience.
• Experience mentoring other team members.
• Passion and demonstrated experience for challenging security assumptions.
• Excellent written and verbal communication skills and ability to communicate your findings at many different levels of abstraction from Engineers to Executives.
• Passion for fixing security issues and not just identifying security issues.
• Familiarity with common network protocols and standards such as DNS and TCP/IP.
• Experience with MacOS and Linux.
• Experience with leveraging components of a modern software development stack to attack companies, including CI, container orchestration systems (Kubernetes/Docker), cloud providers (AWS, GCP), etc and be able to give hardening suggestions.
• Experience/knowledge of defensive tools/techniques (IDS/IPS, Packet Capture, Network Analysis, AV, EDR, etc.) and how to evade them.
• Deep understanding of Mitre’s ATT&CK Framework.
• Strong understanding of the security fundamentals of access and identity.
• Comfortable reading / writing python, go, and javascript.
• Ability to research and execute a testing plan to access a new technology or process.
• Demonstrated experience working with a distributed team.
• Proficiency to communicate over a text-based medium (Slack, JIRA Issues, GitHub issues, & Email) and can succinctly document technical details.

Bonus points

• Experience in the Financial Technology domain.
• Experience being a technical lead at other organizations.

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

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.

Base Pay Range: Toronto, ON $136,000 — $160,000 CAD

Note: This description previously included a link-driven line about Total Rewards; placeholders were retained sans links to comply with formatting guidelines.

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