Support Delivery - Ontario - Remote

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 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 onboardingance 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 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 the full spectrum of humanity.

We are an equal opportunity employeration, or other applicable legally protected characteristic.

Background checks for applicants will be administered in accordance with applicable lawation technology systems and related data security obligations.

To notify OpenAI that you believe this job posting is non-compliant. No response will be provided to inquiries unrelated to job posting compliance.

We are committed to providing reasonable accommodations to applicants with disabilities.

At OpenAI, we believe artificial intelligence has the potential to help people solve immense global challenges, and we want the upside of AI to be widely shared. Join us in shaping the future of technology.

Compensation

CA$140K – CA$188K + Offers Equity

The base pay offered may vary depending on multiple individualized factorsance-related bonus(es) for eligible employees, and the following benefits.

- Medical, dental, and vision insurance for you and your family

- Paid parental leave (up to 24 weeks for birth parents and 20 weeks for non-birthing parents)

- Paid time off: accrual of 20 days per calendar year

- 12+ paid company holidays, and multiple paid coordinated company office closures throughout the year for focus and recharge, plus paid sick time

More details about our perks are available to candidates during the hiring process.

This role is at-will and OpenAI reserves the right to modify base pay and other compensation components at any time based on individual performance, team or company results, or market conditions.

📌 Cyber Operations Strategist, Critical Harm Operations (Ontario)
🏢 OpenAI
📍 Ontario