Chief of Staff – AI

Human Agency

. Partner with the Managing Director of AI and executive team to translate priorities into sequenced plans, resourcing, and measurable outcomes .

Posted 10/30/2026full-timeRemote • Canada, United StatesLeadWebsite

Core Competencies

Role fit

Core Competencies

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Demonstrates expertise in leading AI transformation initiatives, including the design and implementation of AI-enabled processes and systems. Proficient in managing client engagements, stakeholder alignment, and delivering measurable outcomes while ensuring ethical practices in AI.

Highest-signal resume keywords

AI Transformation MethodologyLLM-Enabled Solutions ImplementationPrompt EngineeringWorkflow AutomationStakeholder Alignment

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

Project ManagementChange ManagementRisk ManagementProcess DesignKnowledge Management Systems

Soft Skills

CommunicationLeadershipCollaborationProblem-Solving

Tools & Technologies

Google WorkspaceAsanaNotionSlackAutomation Platforms

Industry Keywords

AI CapabilitiesResponsible AIEthical PracticesClient ServicesOrganizational Change

About the role

Key responsibilities & impact

Partner with the Managing Director of AI and executive team to translate priorities into sequenced plans, resourcing, and measurable outcomes
Lead Human Agency's AI transformation methodology, including offerings, repeatable frameworks, and best practices
Design AI-enabled processes using LLMs, automation platforms, and knowledge assistants
Build independent, scalable AI-powered systems, prompts, playbooks, knowledge bases, and monitoring loops
Own end-to-end delivery of multiple client AI engagements from discovery through launch and sustained adoption
Lead company-wide and client-wide AI adoption initiatives, including stakeholder alignment, training, governance, and measurement
Conduct discovery, define use cases and success metrics, assess risks and technical requirements, and create scopes, timelines, and acceptance criteria
Coordinate solution build-outs, tool selection, integrations, prompt engineering, and rollout planning
Establish evaluation routines, quality assurance, safety checks, governance frameworks, and performance monitoring
Lead client check-ins, executive presentations, demos, decision logs, and release notes
Create user guides, FAQs, training programs, and governance playbooks
Design and improve AI work operations from intake through measurement
Manage staffing, subcontractors, budgets, scopes, vendors, delivery dashboards, risks, and dependencies
Prepare executive briefings and presentations and report progress, risks, and decisions to the Managing Director of AI
Contribute to AI thought leadership through best-practice documentation, case studies, and insights

Requirements

What you’ll need

5–7+ years in operations, client services, product/program/project management, strategic support, consulting, or transformation roles with direct ownership of client-facing delivery
Demonstrated success leading multi-stakeholder projects and organizational change initiatives end-to-end, including scope, timelines, budgets, risk, and change management
Hands-on experience implementing LLM-enabled solutions, prompt engineering, workflow automation, and knowledge management systems
Strong understanding of AI capabilities and limitations, reliability design, and responsible risk management
Proven ability to design repeatable processes and systems that scale beyond individual projects
Experience with no/low-code automation platforms, knowledge bases, and modern AI tooling
High proficiency with Google Workspace, Asana/Notion, Slack, modern web and content tools, and polished executive documents and presentations
Ability 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, including transparency, human oversight, privacy, and bias mitigation
US applicants: full-time employment; Canadian applicants: independent contractor arrangement
Ability to travel regularly, 20–40%
Bonus: experience leading organizational-level technology rollouts, management consulting background, responsible AI familiarity, or AI/ML product development experience

Benefits

Comp & perks

Performance-based bonuses
Potential equity participation
Autonomy to lead
Resources to succeed
Room to grow
Clear pathways to increased leadership responsibility
Regular travel opportunities for client activities, organizational rollouts, and events