Cyber Operations Strategist, Critical Harm Operations
Remote • Ontario - Remote • FullTime
Posted 18d ago
Remote Work Policy
Fully remote
Employment Type
FullTime
Categories
Applied AI Engineer
About the job
We are seeking a senior cybersecurity practitioner and operations strategist to enhance the quality, scalability, and technical rigor of our Cyber Operations. This role involves a blend of hands-on cyber judgment and systems-level operating design. You will tackle complex dual-use questions, refine standard operating procedures (SOPs), improve reviewer and vendor performance, and develop practical tools and automations. Success in this senior individual contributor role is measured by durable improvements in the operating model and the effectiveness of the reviewers who execute it. This position, based in Toronto, is currently remote and is expected to transition to an in-office arrangement.
Responsibilities
- Drive the Cyber Operations operating model across domain priorities, SOPs, escalation paths, quality health, vendor capability, and roadmap inputs, while informing trusted access strategies.
- Act as the senior cyber expert for complex or high-risk decisions concerning ChatGPT, API, Codex, agents, and emerging product surfaces.
- Translate policy ambiguities, quality issues, appeals, and reviewer disagreements into clear decision rules, calibration examples, training materials, and tooling requirements.
- Build robust operating systems and quality loops, including golden sets, holdouts, double-labeling, adjudication, error taxonomies, reviewer calibration, and automation evaluations.
- Enhance FTE and BPO capabilities through onboarding, certification, coaching, recurring calibration, and vendor performance partnerships.
- Utilize quality, appeals, SLA, backlog, and disagreement signals to diagnose root causes and prioritize high-impact fixes.
- Develop hands-on solutions such as SQL analyses, scripts, dashboards, LLM evaluation workflows, evidence enrichment, routing logic, and lightweight automations to improve decision quality and reduce manual effort.
- Collaborate with Policy, Integrity, Safety Systems, Security, Legal, Product, Engineering, and Investigations teams to operationalize changes and ensure launch readiness.
Requirements
- Possess 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.
- Demonstrate deep reasoning capabilities regarding attacker tradecraft, vulnerability exploitation, credential abuse, malware, persistence, evasion, exfiltration, cloud or identity abuse, and ambiguous dual-use activity.
- Experience building or improving high-stakes operations, reviewer programs, QA systems, escalation workflows, or vendor/BPO programs.
- Ability to translate complex cyber and policy judgments into reviewer-usable SOPs, decision trees, training, and concise written recommendations.
- Proficiency in using SQL, Python, C/C++, JavaScript, PowerShell, and Bash, APIs, LLM tooling, or automation to solve operational problems.
- Understanding of human-in-the-loop automation, evaluations, monitoring, holdouts, and fallback paths for sensitive workflows.
- Ability to operate independently in ambiguous environments, communicate clearly across technical and non-technical audiences, and exercise sound judgment and discretion when handling sensitive material.
- Experience with trust and safety, platform abuse, cyber misuse of AI systems, or LLM safety.
- Experience with golden sets, classifier or prompt evaluations, and reviewer-quality programs.
- Experience enabling global vendor reviewer operations.