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Remote · Canada
CA$140K–CA$188K/yr
Published by the employer
About the Team
Critical Harm Operations sits within User Safety & Risk Operations and builds enforcement systems for Frontier Risk and Material Harm that are accurate, fast, defensible, and built to scale. The Cyber vertical turns policy into reviewer standards, calibrated judgment, quality systems, escalation paths, and automation guardrails.
About the Role
We are looking for a senior cybersecurity practitioner and operations strategist to raise the quality, scalability, and technical rigor of our Cyber Operations. You will combine hands-on cyber judgment with systems-level operating design: resolve the hardest dual-use questions, evolve SOPs, uplift reviewers and vendors, and build practical tools and automations.
This is a senior IC role. Success is not primarily cases closed; it is durable improvement in the operating model and the reviewers who run it.
This Toronto-based role is currently remote and is expected to transition to an in-office arrangement.
In this role, you will:
Drive the Cyber Operations operating model across domain priorities, SOPs, escalation paths, quality health, vendor capability, roadmap inputs and help inform trusted access strategies.
Serve as the senior cyber expert for complex or high-risk decisions across ChatGPT, API, Codex, agents, and emerging product surfaces.
Translate policy ambiguity, quality misses, appeals, and reviewer disagreement into clear decision rules, calibration examples, training, and tooling requirements.
Build durable operating systems and quality loops: golden sets, holdouts, double-labeling, adjudication, error taxonomies, reviewer calibration, and automation evaluations.
Raise FTE and BPO capability through onboarding, certification, coaching, recurring calibration, and vendor-performance partnership.
Use quality, appeals, SLA, backlog, and disagreement signals to diagnose root causes and prioritize high-leverage fixes.
Build hands-on solutions—SQL analyses, scripts, dashboards, LLM eval workflows, evidence enrichment, routing logic, and lightweight automations—that improve decision quality and reduce manual effort.
Partner with Policy, Integrity, Safety Systems, Security, Legal, Product, Engineering, and Investigations to operationalize changes and drive launch readiness.
You might thrive in this role if you have:
Have 8+ years of hands-on cybersecurity experience in offensive security, threat intelligence, incident response, security research, red teaming, application security, DFIR, malware analysis, or a related field.
Can reason deeply about attacker tradecraft, vulnerability exploitation, credential abuse, malware, persistence, evasion, exfiltration, cloud or identity abuse, and ambiguous dual-use activity.
Have built or improved high-stakes operations, reviewer programs, QA systems, escalation workflows, or vendor/BPO programs.
Can turn complex cyber and policy judgment into reviewer-usable SOPs, decision trees, training, and concise written recommendations.
Are comfortable using SQL, Python, Python, C/C++, JavaScript, PowerShell, and Bash, APIs, LLM tooling, or automation to solve operational problems.
Understand human-in-the-loop automation, evaluations, monitoring, holdouts, and fallback paths for sensitive workflows.
Operate independently in ambiguity, communicate clearly across technical and non-technical audiences, and bring sound judgment and discretion when handling sensitive material.
Experience with trust and safety, platform abuse, cyber misuse of AI systems, or LLM safety.
Nice to have:
Experience with golden sets, classifier or prompt evaluations, and reviewer-quality programs.
Experience enabling global vendor reviewer operations.
About OpenAI
OpenAI is an AI research and deployment company dedicated to ensuring that general-purpose artificial intelligence benefits all of humanity. We push the boundaries of the capabilities of AI systems and seek to safely deploy them to the world through our products. AI is an extremely powerful tool that must be created with safety and human needs at its core, and to achieve our mission, we must encompass and value the many different perspectives, voices, and experiences that form the full spectrum of humanity.
We are an equal opportunity employer, and we do not discriminate on the basis of race, religion, color, national origin, sex, sexual orientation, age, veteran status, disability, genetic information, or other applicable legally protected characteristic.
For additional information, please see OpenAI’s Affirmative Action and Equal Employment Opportunity Policy Statement.
Background checks for applicants will be administered in accordance with applicable law, and qualified applicants with arrest or conviction records will be considered for employment consistent with those laws, including the San Francisco Fair Chance Ordinance, the Los Angeles County Fair Chance Ordinance for Employers, and the California Fair Chance Act, for US-based candidates. For unincorporated Los Angeles County workers: we reasonably believe that criminal history may have a direct, adverse and negative relationship with the following job duties, potentially resulting in the withdrawal of a conditional offer of employment: protect computer hardware entrusted to you from theft, loss or damage; return all computer hardware in your possession (including the data contained therein) upon termination of employment or end of assignment; and maintain the confidentiality of proprietary, confidential, and non-public information. In addition, job duties require access to secure and protected information technology systems and related data security obligations.
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