Staff AI Operations Lead

This is a fully remote position, open to applicants in Canada.

📋 Description

• Collaborate with department leaders to pinpoint high-impact workflows and assess the potential for AI models to contribute.

• Establish success metrics such as cycle time, quality, cost, and risk; ensure honest instrumentation and reporting of results.

• Deliver systems ready for production, complete with evaluation harnesses, human-in-the-loop reviews, and ongoing monitoring.

• Foster user adoption through research, comprehensive documentation, and implementation strategies.

• Develop frameworks for model access, orchestration, agent management, prompt and tool oversight, evaluation, logging, and cost management.

• Enhance the existing infrastructure of the Data team.

• Co-manage shared components with Engineering and synchronize dependencies within partner roadmaps.

• Create templates, playbooks, golden paths, safety checklists, and evaluation methodologies.

• Conduct office hours, demonstrations, and community-of-practice sessions.

• Produce AI enablement resources for GTM, operations, and leadership.

• Assist teams in discerning when and how to effectively utilize AI.

• Collaborate with Security, IT, and Legal on access control, data management, vendor risk, and policy matters.

• Apply data classification standards to AI applications and delineate audit-trail requirements for sensitive data in LLM pipelines.

⛳️ Requirements

• Extensive experience deploying systems into real business workflows, including the ownership of a production system relied upon daily by non-technical personnel.

• Practical fluency with contemporary AI stacks: LLMs, retrieval, tool usage and agents, evaluation, and guardrails.

• Capability to deeply understand business functions to enhance workflows.

• Proven track record of leading cross-functional projects without formal authority.

• Comfort in navigating security, privacy, and compliance trade-offs, including data classification, retention, access controls, and vendor risk.

• Strong teaching abilities, effective writing skills, and the capability to simplify complex concepts.

• Demonstrated capacity to stay updated as the AI landscape evolves and to adapt based on evidence.

• Proficiency in SQL and familiarity with a modern data stack (dbt, cloud warehouse, BI tools) is a plus.

• Experience with workflow automation or enterprise systems such as case management, ticketing, CRM, and knowledge bases is a plus.

• Knowledge of observability practices for AI systems, including monitoring, quality signals, evaluation pipelines, cost, and latency analysis is a plus.

• Experience in change management within a distributed, multi-functional organization is a plus.

• Interest in external advocacy, including writing, speaking, podcasts, and peer groups is a plus.

• Must be eligible to work in Canada; visa sponsorship or transfers are not available.

🏝️ Benefits

• Generous equity participation with an employee-friendly stock program.

• Transparent compensation based on levels relative to experience.

• Unlimited paid time off (PTO).

• A distributed-first mindset and culture.

• Stipends for home office, co-working, and internet expenses.

• Comprehensive benefits coverage for employees, with additional options for dependents.

• Up to 16 weeks of paid parental leave, irrespective of the path to parenthood.

• Annual development allowance.

• Reasonable accommodations provided during the hiring process.