Chief of Staff – Managing Director of 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 LLM-enabled solutions and automation processes. Proven ability to manage multi-stakeholder projects, ensuring alignment, governance, and measurable outcomes while maintaining a commitment to ethical AI practices.

Highest-signal resume keywords

AI Transformation MethodologyLLM-Enabled Solutions ImplementationPrompt EngineeringChange ManagementStakeholder Alignment

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

Project ManagementWorkflow AutomationKnowledge Management SystemsRisk ManagementProcess DesignAI Capabilities UnderstandingBudget ManagementQuality AssuranceEvaluation RoutinesContinuous Improvement

Soft Skills

CommunicationLeadershipCollaborationPresentation SkillsClient Engagement

Tools & Technologies

Google WorkspaceAsanaNotionSlackZapierN8n

Industry Keywords

AI AdoptionEthical AIHuman OversightBias MitigationTransformation Roles

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 AI-powered systems, repeatable implementation processes, 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 requirements, and create scopes, timelines, and acceptance criteria
Coordinate solution build-outs, integrations, prompt engineering, and rollout planning with internal teammates and external partners
Design change-management approaches and partner with client leadership to sequence rollouts and demonstrate ROI
Establish evaluation, quality assurance, safety, governance, monitoring, and continuous improvement routines
Lead client check-ins, executive presentations, demos, decision logs, release notes, and enablement materials
Manage staffing, subcontractors, budgets, scopes, vendors, delivery dashboards, and project cadences
Prepare executive briefings and reports on progress, risks, and decisions
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 such as Zapier or n8n, knowledge bases, and modern AI tooling
High proficiency with Google Workspace, Asana/Notion, Slack, and modern web and content tools
Experience preparing 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
Ability to travel regularly, 20–40%

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