Chief of Staff – Managing Director of 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 allocation, and measurable results.

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

• Create AI-enhanced processes utilizing LLMs, automation platforms, and knowledge assistants.

• Develop self-sufficient AI-driven systems, standardized implementation processes, prompts, playbooks, knowledge repositories, and monitoring loops.

• Take charge of the complete delivery of numerous client AI projects from initial discovery to launch and ongoing adoption.

• Spearhead company-wide and client-focused AI adoption initiatives, which include stakeholder alignment, training, governance, and performance measurement.

• Conduct discovery sessions, outline use cases and success metrics, evaluate risks and requirements, and formulate scopes, timelines, and acceptance criteria.

• Coordinate the development of solutions, integrations, prompt engineering, and rollout planning with internal teams and external partners.

• Design change management strategies and collaborate with client leadership to sequence rollouts and showcase return on investment (ROI).

• Establish routines for evaluation, quality assurance, safety, governance, monitoring, and continuous improvement.

• Lead client check-ins, executive presentations, demonstrations, decision logs, release notes, and enablement materials.

• Oversee staffing, subcontractors, budgets, scopes, vendors, delivery dashboards, and project timelines.

• Prepare executive briefings and reports outlining progress, risks, and decisions made.

• Contribute to AI thought leadership through documentation of best practices, 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 track record in leading multi-stakeholder projects and organizational change initiatives from start to finish, including scope, timelines, budgets, risk management, and change management.

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

• Strong comprehension 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 like Zapier or n8n, knowledge bases, and contemporary AI tools.

• High proficiency in Google Workspace, Asana/Notion, Slack, and modern web and content tools.

• Experience in preparing polished executive documents and presentations.

• Capability to communicate complex technical concepts in terms of 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% of the time.

🏝️ Benefits

• Performance-based bonuses.

• Potential for equity participation.

• Autonomy to lead initiatives.

• Resources available to ensure success.

• Opportunities for professional growth.

• Clear pathways to increased leadership responsibilities.

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