Chief of Staff – Managing Director, AI

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

📋 Description

• Collaborate with the Managing Director of AI and the executive team to transform priorities into actionable plans, resource allocation, and measurable outcomes.

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

• Create AI-enabled processes and automated systems utilizing LLMs, automation platforms, and knowledge assistants.

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

• Develop repeatable AI implementation processes, including prompts, playbooks, knowledge bases, evaluation routines, governance models, and monitoring systems.

• Oversee the comprehensive delivery of various client AI engagements from discovery to launch and ongoing adoption.

• Lead company-wide and client-focused AI adoption initiatives, ensuring stakeholder alignment, training, governance, and measurement.

• Manage solution build-outs involving data/connectivity, tool selection, integrations, prompt engineering, and rollouts.

• Formulate change-management strategies and collaborate with client leadership to schedule rollouts and demonstrate ROI.

• Establish practices for quality, safety, evaluation, monitoring, and responsible AI governance.

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

• Design and enhance the AI operating system from intake to measurement.

• Oversee staffing, subcontractors, budgets, scopes, vendors, dashboards, risks, dependencies, and meeting frequencies.

• Prepare executive-level communications and report on progress, risks, and decisions to the Managing Director of AI.

• Contribute to AI thought leadership through documentation of best practices, case studies, and insights.

⛳️ Requirements

• Location: US or Canada.

• US Applicants: Full-Time; Canadian Applicants: Independent Contractor.

• 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.

• Hands-on 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.

• Demonstrated ability to design repeatable processes and scalable systems.

• Experience using no/low-code automation platforms such as Zapier or n8n, knowledge bases, and contemporary AI tools.

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

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

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

• Bachelor's degree or equivalent experience.

• Availability for regular travel of 20–40%.

• Bonus experience in organizational-level technology rollouts, management consulting, responsible AI, or AI/ML product development.

🏝️ Benefits

• Performance-based bonuses.

• Potential for equity participation.

• Autonomy to lead projects.

• Resources available for success.

• Opportunities for professional growth.

• Clear pathways to increased leadership responsibilities.

• Remote-friendly work arrangement.