Chief of Staff – Managing Director, AI

Human Agency

. Partner with the Managing Director of AI and executive team to translate priorities into 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, designing scalable AI-enabled processes, and managing client engagements from discovery to adoption. Proficient in implementing LLM-enabled solutions and fostering organizational change through effective training and governance.

Highest-signal resume keywords

AI Transformation MethodologyLLM-Enabled Solutions ImplementationProject ManagementStakeholder EngagementGovernance Frameworks

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

Prompt EngineeringWorkflow AutomationKnowledge Management SystemsProcess DesignRisk ManagementChange ManagementQuality AssuranceEvaluation RoutinesClient DeliveryAI Capabilities Understanding

Soft Skills

CommunicationLeadershipTrainingCollaborationPresentation Skills

Tools & Technologies

Google WorkspaceAsanaNotionSlackAutomation Platforms

Industry Keywords

AI AdoptionClient ServicesOperations ManagementStrategic SupportEthical AI Practices

About the role

Key responsibilities & impact

Partner with the Managing Director of AI and executive team to translate priorities into plans, resourcing, and measurable outcomes
Lead Human Agency's AI transformation methodology and define repeatable frameworks and best practices
Design AI-enabled processes using LLMs, automation platforms, and knowledge assistants
Build scalable AI-powered systems, prompts, playbooks, knowledge bases, monitoring, and feedback 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 alignment, training, governance, and measurement
Coordinate solution build-outs with internal teammates and external partners
Establish evaluation routines, quality assurance, safety checks, UAT plans, and governance frameworks
Lead client check-ins, executive presentations, demos, decision logs, and release notes
Create enablement materials, training programs, and governance playbooks
Design and improve the operating system for AI work across intake, delivery, QA, launch, and measurement
Manage staffing, subcontractors, budgets, scopes, vendors, dashboards, and meeting cadences
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 (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, 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
Regular travel of 20–40%
Remote-friendly, with preference for candidates in major tech hubs

Benefits

Comp & perks

Performance-based bonuses
Potential equity participation
Autonomy to lead
Resources to succeed
Room to grow
Clear pathways to increased leadership responsibility