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Cyber Operations Strategist, Critical Harm Operations

OpenAI· User Operations
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Hybrid (Ontario - Remote)CA$140k - CA$188kFull-timePosted 1mo ago

About the role

Senior cybersecurity practitioner and operations strategist to raise the quality, scalability, and technical rigor of OpenAI's Cyber Operations within Critical Harm Operations, with a focus on turning policy into reviewer standards, calibration, and practical tooling.

Responsibilities

  • 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.

Qualifications

  • 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, 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.

Skills

Required:Cybersecurity leadership and operations designPolicy-to-implementation translationTechnical tooling and automation

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
Last updated Oct 1, 2026. Interested? Apply on the company site.

About OpenAI

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