Chief of Staff – Managing Director, 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 actionable plans, resource allocations, and measurable results.

• Spearhead Human Agency's AI transformation approach, establishing repeatable frameworks and best practices.

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

• Create scalable AI-powered systems, including prompts, playbooks, knowledge bases, monitoring systems, and feedback mechanisms.

• Take ownership of the complete delivery process for multiple client AI projects from the discovery phase through to launch and ongoing adoption.

• Drive company-wide and client-wide AI adoption efforts, focusing on alignment, training, governance, and metrics.

• Coordinate the development of solutions alongside internal teams and external collaborators.

• Set up evaluation protocols, quality assurance measures, safety checks, user acceptance testing plans, and governance structures.

• Conduct client check-ins, deliver executive presentations, demos, maintain decision logs, and provide release notes.

• Develop enablement resources, training programs, and governance playbooks.

• Design and enhance the operational framework for AI initiatives covering intake, delivery, quality assurance, launch, and evaluation.

• Oversee staffing, subcontractors, budgets, scopes, vendors, dashboards, and meeting schedules.

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

• 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 of leading multi-stakeholder projects and organizational change initiatives from start to finish (including scope, timelines, budgets, risk, and change management).

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

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

• Established ability to create repeatable processes and systems that 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 creating polished executive documents and presentations.

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

• Bachelor’s degree or comparable experience.

• Commitment to ethical practices and responsible AI usage.

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

• Remote-friendly position, with a preference for candidates located in major tech hubs.

🏝️ Benefits

• Performance-based bonuses.

• Potential for equity participation.

• Autonomy to lead initiatives.

• Resources available for success.

• Opportunities for professional growth.

• Clear pathways to increased leadership roles.