Chief of Staff to the Managing Director of AI

Human Agency•Montreal, QC

11d•Remote

About The Position

Human Agency is rapidly scaling and seeks exceptional talent to drive its next chapter of growth. The company values doers, leaders who are hands-on, and teams that work flat, fostering a culture where the best ideas win and client outcomes are paramount. They partner with organizations of all sizes to explore, design, and implement secure, scalable, and human-centered AI strategies, believing AI should amplify human potential. Their work spans advisory, tooling, implementation, and education, aiming to empower teams to work smarter and unlock new possibilities through thoughtful, responsible innovation. The company emphasizes purpose, love, and adventure in its work. The opportunity is for an exceptional Chief of Staff for the Managing Director of AI, who will combine strategic AI vision with hands-on execution and technological know-how. This role involves being a force-multiplier and transformation architect, designing AI-enabled processes, building automated engines, leading organizational rollouts, and ensuring crisp execution across AI solutions. It goes beyond traditional Chief of Staff duties, focusing on designing scalable, repeatable AI systems and leading client transformations from discovery to sustained adoption, with potential for growth into leading organizational-level AI implementations.

Requirements

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)
Deep AI fluency: hands-on experience implementing LLM-enabled solutions, prompt engineering, workflow automation, and knowledge management systems; can shape prompts/playbooks, evaluate quality, and choose appropriate tools or vendors
Strong understanding of AI capabilities and limitations, when to use AI, how to design for reliability, and how to manage risks responsibly
Proven ability to design repeatable processes and systems that scale beyond individual projects
Experience with no/low-code automation platforms (e.g., Zapier/n8n), knowledge bases, and modern AI tooling
High proficiency with Google Workspace, Asana/Notion, Slack, and comfort with modern web and content tools; experience preparing polished executive documents and presentations
Exceptional 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 (transparency, human oversight, privacy, bias mitigation)

Nice To Haves

Experience leading organizational-level technology rollouts
Background in management consulting
Familiarity with responsible AI considerations (privacy, data handling, consent, bias mitigation)
Experience in AI/ML product development
An advanced degree in business, technology, or a related field

Responsibilities

Partner with the Managing Director of AI and the executive team to translate priorities into sequenced plans, resourcing, and measurable outcomes
Lead Human Agency's AI transformation methodology: define offerings, build repeatable frameworks, and establish best practices for AI-enabled workflows
Design end-to-end processes that embed AI tools (LLMs, automation platforms, knowledge assistants) into client workflows and internal operations
Translate complex AI capabilities into clear business cases, use cases, and implementation roadmaps for executive audiences
Produce high-quality executive materials (briefings, roadmaps, decision memos) that drive alignment and decisions
Identify where AI creates leverage across client engagements and surface strategic opportunities to leadership
Design and build AI-powered systems that operate independently with minimal ongoing intervention—automated engines that scale beyond individual engagements
Create repeatable processes for AI implementation: discovery frameworks, solution architectures, evaluation routines, and governance models
Design prompts, playbooks, and knowledge bases optimized for reliability, consistency, and reusability across multiple clients
Implement lightweight automation using no/low-code tools (Zapier, Make, Airtable) integrated with AI capabilities
Establish monitoring and feedback loops that enable self-correcting, continuously improving systems
Document patterns and best practices that can be deployed at scale
Own end-to-end delivery on multiple client engagements involving AI-enabled solutions (e.g., knowledge assistants, workflow automations, content summarization, research copilots), from discovery through launch and sustained adoption
Lead company-wide and client-wide AI adoption initiatives—managing stakeholder alignment, training, governance, and measurement across entire organizations
Run comprehensive discovery to surface use cases, success metrics, risks, change-management needs, and technical requirements; translate findings into scopes, timelines, and clear acceptance criteria
Coordinate solution build-outs with internal teammates and external partners: data/connectivity needs, tool selection, integration planning, prompt engineering, and rollout choreography
Design change-management approaches that address skill gaps, cultural resistance, workflow disruption, and organizational readiness
Partner with client leadership to sequence rollout phases, manage dependencies, and demonstrate ROI
Set lightweight evaluation routines: accuracy metrics, latency benchmarks, cost tracking, quality assurance processes, and continuous improvement cycles
Establish prompt/playbook management, basic safety/guardrail checks, and UAT plans
Build governance frameworks that enable responsible, scalable AI adoption across organizations
Implement monitoring systems that track performance, usage, and business impact
Lead standing client check-ins, executive presentations, demo readiness, decision logs, and release notes, presenting succinct options and recommendations
Create comprehensive enablement materials: user guides, FAQs, training programs, and governance playbooks that empower client teams to operate AI systems independently
Build lasting client relationships through proactive communication, anticipation of needs, and consistent delivery quality
Present to executive audiences with clarity and confidence, addressing concerns about accuracy, security, and adoption
Design and continuously improve the operating system for AI work: intake → triage → prioritization → delivery → QA → launch → measurement
Manage staffing assignments and subcontractor contributions across concurrent workstreams; keep tools current (Asana/Notion, Google Workspace, Slack)
Budget & scope control: track time against SOWs, flag changes early, manage vendors, and ensure on-budget delivery with clear documentation
Establish shared dashboards for delivery health (timeline, risk, burn, dependency status) and run tight meeting cadences
Prepare agendas, briefings, and executive-ready presentations; synthesize complex information into actionable insights
Provide clear, timely reporting to the Managing Director of AI and stakeholders on progress, risks, and decisions
Contribute to Human Agency's AI thought leadership through documentation of best practices, case studies, and insights