Humanagency
Chief of Staff to the Managing Director of AI
Toronto, Canada · Exec · Contract
Sponsorship not specified$20k-$40kDetected 8 days ago
Machine LearningLLMsDesign SystemsProject ManagementStakeholder ManagementResearchLeadershipCommunicationPublic Speaking
About the role
- We are seeking an exceptional Chief of Staff for our Managing Director of AI-someone who combines strategic vision in AI with hands-on execution and technological know-how.
- This role goes beyond traditional Chief of Staff responsibilities.
- You have the potential to grow into leading organizational-level AI implementations as the practice expands.
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
- 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
- AI Process Design & Automated Engines
- 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
Requirements
- Experience & Skills
- Deep AI fluency: hands-on experience implementing LLM-enabled solutions, prompt engineering, workflow automation, and knowledge management systems
- Strong understanding of AI capabilities and limitations, when to use AI, how to design for reliability, and how to manage risks responsibly
- 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
- Exceptional ability to translate complex technical concepts into clear business value for non-technical audiences
Nice to have
- Bachelor's degree or equivalent experience
- an advanced degree in business, technology, or a related field is a plus
Skills
- Translate complex AI capabilities into clear business cases, use cases, and implementation roadmaps for executive audiences
- Establish monitoring and feedback loops that enable self-correcting, continuously improving systems
- Establish prompt/playbook management, basic safety/guardrail checks, and UAT plans
Compensation
- $20k-$40k
Benefits
- Our mission is to bring on individuals, from creative producers to technical experts to entrepreneurial leaders, who can help us realize this next chapter of growth.
Company info
- We are a company of doers.
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