Chief of Staff – AI

This is a fully remote position, open to applicants in Canada, +1 more country.

📋 Description

• Collaborate with the Managing Director of AI and the executive team to convert priorities into organized plans, resource allocations, and measurable outcomes.

• Spearhead Human Agency's AI transformation methodology, encompassing offerings, repeatable frameworks, and best practices.

• Create AI-enhanced client and internal workflows utilizing LLMs, automation platforms, and knowledge assistants.

• Convert AI capabilities into business cases, use cases, implementation roadmaps, briefings, and decision memos.

• Develop independent AI-driven systems, automated engines, prompts, playbooks, knowledge bases, and monitoring loops.

• Oversee the complete delivery of multiple AI-enhanced client engagements from the discovery phase through to launch and sustained adoption.

• Lead organization-wide and client-wide initiatives for AI adoption, including stakeholder alignment, training, governance, and metrics.

• Coordinate solution development involving data connectivity, tool selection, integrations, prompt engineering, and rollout planning.

• Establish frameworks for evaluation, quality assurance, safety, governance, and monitoring.

• Conduct client check-ins, executive presentations, demos, decision logs, release notes, user guides, FAQs, training programs, and governance playbooks.

• Design and refine AI operations across intake, triage, prioritization, delivery, QA, launch, and measurement.

• Manage staffing, subcontractors, budgets, project scope, vendors, delivery dashboards, risks, dependencies, and meeting schedules.

• Report on progress, risks, and decisions to the Managing Director of AI and stakeholders.

• Contribute to AI thought leadership through best-practice documentation, case studies, and insights.

⛳️ Requirements

• 5-7+ years in operations, client services, product/program/project management, strategic support, consulting, or transformation roles with direct responsibility for client-facing delivery.

• Proven track record in leading multi-stakeholder projects and organizational change initiatives from start to finish, including managing scope, timelines, budgets, risk, and change management.

• Hands-on experience in implementing LLM-enabled solutions, prompt engineering, workflow automation, and knowledge management systems.

• Solid understanding of AI capabilities and limitations, reliability, and responsible risk management practices.

• Demonstrated ability to design scalable, repeatable processes and systems that extend beyond individual projects.

• Familiarity with no/low-code automation platforms, knowledge bases, and contemporary AI tools.

• High proficiency with Google Workspace, Asana/Notion, Slack, modern web and content tools, as well as polished executive documents and presentations.

• Exceptional skill in translating complex technical concepts into clear business value for non-technical audiences.

• Bachelor's degree or equivalent experience.

• Commitment to ethical practices and responsible AI, including transparency, human oversight, privacy, and bias mitigation.

• Willingness to travel regularly (20–40%) for client activities, organizational rollouts, and events.

• US applicants must be eligible for full-time employment; Canadian applicants must be capable of working as independent contractors.

🏝️ Benefits

• Performance-based bonuses.

• Potential equity participation.

• Autonomy to lead.

• Resources to achieve success.

• Opportunities for growth.

• Clear pathways to increased leadership responsibilities.