Chief of Staff to the Managing Director of AI

Remote
Human Agency Chicago, IL
Full Time Executive Level 5+ years

Posted 3 weeks ago

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About This Role

This role is for a Chief of Staff to the Managing Director of AI, combining strategic vision with hands-on execution to design AI-enabled processes, build automated systems, and lead organizational rollouts of AI solutions. The successful candidate will drive crisp execution across the company's AI solutions practice and has the potential to grow into leading organizational-level AI implementations.

Responsibilities

  • 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, defining offerings, building repeatable frameworks, and establishing best practices
  • Design end-to-end processes embedding AI tools (LLMs, automation platforms) into client workflows and internal operations
  • Translate complex AI capabilities into clear business 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
  • Own end-to-end delivery on multiple client engagements involving AI-enabled solutions
  • Lead company-wide and client-wide AI adoption initiatives, managing stakeholder alignment, training, and governance
  • Design change-management approaches that address skill gaps, cultural resistance, and workflow disruption

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
  • 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
  • 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
  • Exceptional ability to translate complex technical concepts into clear business value for non-technical audiences

Qualifications

  • Bachelor's degree or equivalent experience
  • 5-7+ years in operations, client services, product/program/project management, strategic support, consulting, or transformation roles with direct ownership of client-facing delivery

Nice to Have

  • 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
  • Advanced degree in business, technology, or a related field

Skills

Problem Solving * Google Workspace * Communication * Airtable * Asana * LLMs * Notion * Slack * Prompt Engineering * Make * Zapier * Strategic * workflow automation * Knowledge Management Systems *

* Required skills

Benefits

Potential equity participation

About Human Agency

Human Agency partners with organizations to explore, design, and implement AI strategies that are secure, scalable, and human-centered, focusing on amplifying human potential.

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