Chief of Staff to the Managing Director of AI - Chicago, IL Chicago, IL

Chief of Staff to the Managing Director of AI - Chicago, IL

Chicago, IL • Location: Chicago, IL (Remote) • Type: Full-Time

About Human Agency

We are scaling rapidly and hiring exceptional talent across disciplines. Our mission is to partner with clients to build AI strategies that are secure, scalable, and human‑centered. We value doers, flat teams, and transparency. Clients trust us to deliver high‑impact, user‑centric solutions in every engagement.

The Opportunity

We are seeking an exceptional Chief of Staff to the Managing Director of AI. You will combine strategic vision in AI with hands‑on execution, designing AI‑enabled processes, building repeatable automated engines, and leading organizational rollouts across our AI practice.

Key Responsibilities

Strategic & Executive Leadership

• Partner with the Managing Director and 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 and internal operations.
• Translate complex AI capabilities into clear business cases and implementation roadmaps.
• Produce high‑quality executive materials (briefings, roadmaps, decision memos). 
• Identify strategic AI opportunities and surface them to leadership.

AI Process Design & Automated Engines

• Build AI‑powered systems that operate independently with minimal oversight.
• Create repeatable processes for AI implementation: discovery frameworks, solution architectures, evaluation routines, and governance models.
• Design prompts, playbooks, and knowledge bases for reliability, consistency, and reusability.
• Implement lightweight automation using no/low‑code tools (Zapier, Make, Airtable) integrated with AI capabilities.
• Establish monitoring and feedback loops for continuous improvement.
• Document patterns and best practices for scale.

Client Service Delivery & Organizational Rollouts

• Own end‑to‑end delivery on client engagements involving AI‑enabled solutions, from discovery through launch and sustained adoption.
• Lead company‑wide and client‑wide AI adoption initiatives—stakeholder alignment, training, governance, and measurement.
• Conduct discoveries to surface use cases, metrics, risks, and technical requirements.
• Coordinate solution build‑outs with internal teammates and external partners.
• Design change‑management approaches to address skill gaps and cultural resistance.
• Partner with client leadership to sequence rollout phases, manage dependencies, and demonstrate ROI.

Quality, Governance & Evaluation

• Set evaluation routines—accuracy metrics, latency benchmarks, cost tracking, quality assurance, and continuous improvement cycles.
• Establish prompt and playbook management, guardrail checks, and UAT plans.
• Build governance frameworks for responsible, scalable AI adoption.
• Implement monitoring systems that track performance, usage, and business impact.

Stakeholder Management & Enablement

• Lead client check‑ins, executive presentations, demo readiness, decision logs, and release notes.
• Create user guides, FAQs, training programs, and governance playbooks.
• Build lasting client relationships through proactive communication.
• Present to executives with clarity and confidence, addressing accuracy, security, and adoption concerns.

Operations & Project Management

• Manage staffing assignments and subcontractor contributions across concurrent workstreams.
• Control budget and scope—track time against SOWs, flag changes, manage vendors, and ensure on‑budget delivery.
• Establish shared dashboards for delivery health and run tight meeting cadences.

Communications & Reporting

• Prepare agendas, briefings, and executive‑ready presentations.
• Provide timely reporting to the Managing Director of AI and stakeholders.
• Contribute to Human Agency’s AI thought leadership through documentation of best practices and case studies.

Who You Are

Experience & Skills

• 5–7+ years in operations, client services, product/program/project management, strategic support, consulting, transformation roles with direct ownership of client‑facing delivery.
• Demonstrated success leading multi‑stakeholder projects and organizational change initiatives (scope, timelines, budgets, risk, change management).
• Deep AI fluency—hands‑on experience implementing LLM‑enabled solutions, prompt engineering, workflow automation, and knowledge management systems.
• Strong understanding of AI capabilities, limitations, and responsible use.
• Proven ability to design repeatable processes and systems that scale.
• Experience with no/low‑code automation platforms (Zapier, n8n), knowledge bases, and modern AI tooling.
• High proficiency with Google Workspace, Asana/Notion, Slack; comfort with modern web and content tools.
• Exceptional ability to translate complex technical concepts into clear business value for non‑technical audiences.
• Builder and operator: design systems that work without constant oversight.
• Strategic and tactical: set vision while rolling up sleeves for hands‑on implementation.
• 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 escalation versus independent resolution.
• Intellectually curious with strong learning agility and focus on current AI capabilities.
• Comfortable operating in ambiguity and creating structure where none exists.

Considerations

• Education: Bachelor’s degree or equivalent experience; advanced degree is a plus.
• Ethics: Commitment to responsible AI (transparency, oversight, privacy, bias mitigation).
• Travel: Regular (20–40%) for client activities, rollouts, and events.
• Location: Remote‑friendly, preference for major tech hubs.

Compensation

Competitive base salary with performance‑based bonuses and potential equity participation. Final compensation varies with experience, performance, and location.

Why Join Human Agency

Join a team of thinkers and builders creating meaningful impact across sectors—with autonomy to lead, the resources to succeed, and room to grow. Shape how organizations integrate AI at scale and advance into leadership responsibility as our practice expands.

Equal Opportunity Commitment

Human Agency is an Equal Opportunity Employer. We value diverse backgrounds and strive to build an inclusive culture where everyone feels welcomed and empowered.

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