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 structured plans, resource allocations, and measurable outcomes.

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

• Create AI-enabled processes utilizing LLMs, automation tools, and knowledge assistants.

• Develop independent, scalable AI-powered systems, including prompts, playbooks, knowledge bases, and monitoring loops.

• Manage the complete delivery of multiple client AI projects from initial discovery through to launch and sustained adoption.

• Drive company-wide and client-focused AI adoption efforts, addressing stakeholder alignment, training, governance, and evaluation.

• Conduct discovery sessions, define use cases and success metrics, evaluate risks and technical needs, and formulate scopes, timelines, and acceptance criteria.

• Oversee solution development, tool selection, integrations, prompt engineering, and rollout planning.

• Establish evaluation routines, quality assurance measures, safety checks, governance frameworks, and performance monitoring protocols.

• Facilitate client check-ins, executive presentations, demos, decision logs, and release notes.

• Develop user guides, FAQs, training programs, and governance playbooks.

• Design and enhance AI work operations from intake to measurement.

• Manage staffing, subcontractors, budgets, scopes, vendors, delivery dashboards, risks, and dependencies.

• Prepare executive briefings and presentations, reporting on progress, risks, and decisions to the Managing Director of AI.

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

⛳️ Requirements

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

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

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

• Strong knowledge of AI capabilities and limitations, reliability design, and responsible risk management.

• Demonstrated ability to create repeatable processes and systems that can scale beyond individual projects.

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

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

• Capability to translate complex technical concepts into clear business value for non-technical audiences.

• Bachelor's degree or equivalent experience.

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

• For US applicants: full-time employment; for Canadian applicants: independent contractor arrangement.

• Willingness to travel regularly, approximately 20–40% of the time.

• Bonus: experience in leading organizational-level technology rollouts, a background in management consulting, familiarity with responsible AI, or experience in AI/ML product development.

🏝️ Benefits

• Performance-based bonuses.

• Potential for equity participation.

• Autonomy to lead initiatives.

• Resources available for success.

• Opportunities for personal and professional growth.

• Clear pathways to increased leadership roles.

• Regular travel opportunities for client engagements, organizational rollouts, and events.