Chief of Staff to the Managing Director of AI

Human Agency•Chicago, IL

9h•Hybrid

About The Position

Human Agency is a rapidly scaling company focused on exploring, designing, and implementing secure, scalable, and human-centered AI strategies for organizations of all sizes. They believe AI should amplify human potential and build with this conviction in every engagement, offering advisory, tooling, implementation, and education services. The company values doers, leaders who roll up their sleeves, and teams that work flat, fostering a culture of continuous improvement and client-centricity. They prioritize hiring individuals who raise the bar across strategy, engineering, design, data, and operations, leading with purpose, love, and adventure. The opportunity is for an exceptional Chief of Staff to the Managing Director of AI, who will act as a force-multiplier and transformation architect. This role involves 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 AI-powered 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
Builder and operator: You design systems that work without constant oversight, not just execute tasks
Strategic and tactical: Comfortable setting vision while rolling up sleeves for hands-on implementation
AI pragmatist: Excited about possibilities but grounded in what actually delivers measurable value
Mission-driven; systems thinker with bias for action
Clear, persuasive communicator who can influence executive stakeholders and earn trust through delivery
Calm under pressure with excellent judgment about when to escalate vs. solve independently
Able to hold strategic context while driving tactical execution across multiple concurrent engagements
Intellectually curious with strong learning agility, you stay current on AI capabilities and translate findings into practical applications
Comfortable operating in ambiguity and creating structure where none exists
Commitment to ethical practices and responsible AI (transparency, human oversight, privacy, bias mitigation)
Bachelor's degree or equivalent experience

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 is a plus

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