Chief of Staff - Chicago, IL

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

We’re scaling rapidly and have a growing pipeline of opportunities that demand exceptional talent across disciplines. 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.

We are a company of doers. Leaders roll up their sleeves, teams work flat, and everyone contributes to what ships. Titles don’t insulate us from feedback or basics. We invite critique, learn quickly, and keep raising the bar. The best ideas win here, no matter where they come from, because clients trust us to deliver the strongest outcomes every time.

Our clients’ missions, products, and bottom lines are sacred. We immerse ourselves in their world, becoming stewards of their goals and partners in solving big problems. Every product, strategy, or asset we create must be both beautiful and functional; practical, usable, and designed for real-world impact.

Humans are our most valuable resource, and we only grow by hiring people who push us forward. Across strategy, engineering, design, data, and operations, we seek out teammates who raise the bar and make us better. Always hire up, never down.

We partner with organizations of all sizes to explore, design, and implement AI strategies that are secure, scalable, and human-centered. We believe AI should amplify human potential, not replace it and we build with that conviction in every engagement. From advisory and tooling to implementation and education, we meet clients where they are at and help them integrate AI in ways that align with their mission and values. Our goal is to empower teams to work smarter, move faster, and unlock new possibilities through thoughtful, responsible innovation.

And through it all, we lead with purpose, love, and adventure. We do meaningful work with people we care about, and we make the ride an adventure worth taking. Because at Human Agency, who we are and how we work are one and the same.

We are seeking a highly capable and strategic Chief of Staff to lead operational rhythms and high-touch, client-facing delivery—especially where modern AI solutions create leverage. You’ll serve as a force-multiplier to the executive team: aligning priorities, running cross-functional projects, and ensuring crisp execution from intake to impact. You will collaborate closely with account leads and cross-functional teammates across the company.

• Partner with the Managing Director of AI and executive team to translate priorities into sequenced plans, resourcing, and measurable outcomes.
• Maintain focus and accountability on near-term deliverables and long-term goals; surface risks and options early.
• Bring a practical understanding of AI capabilities; convert complex concepts into clear options with trade-offs for leaders and clients.
• Produce high-quality executive materials (briefings, roadmaps, decision memos) that drive alignment and decisions.

• 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 post-launch improvement.
• Run discovery to surface use cases, success metrics, risks, and change-management needs; translate findings into scopes, timelines, and clear acceptance criteria.
• Coordinate solution build-outs with internal teammates and external partners (no engineering management required): data/connectivity needs, tool selection, light integration planning, and rollout choreography.
• Quality & governance: set lightweight evaluation routines (accuracy, latency, cost), prompt/playbook management, basic safety/guardrail checks, and UAT plans.
• Communication & stakeholder management: lead standing client check-ins, demo readiness, decision logs, and release notes—presenting succinct options and recommendations.
• Budget & scope control: track time against SOWs, flag changes early, manage subcontractors, and ensure on-budget delivery with clear documentation.
• Enablement: create simple guides, FAQs, and training sessions to help client teams adopt new AI-enabled workflows.

• Design and continuously improve the operating system for 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).
• 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.

• 5+ years in operations, client services, program/project management, or strategic support roles with direct ownership of client-facing delivery.
• Demonstrated success leading multi-stakeholder projects end-to-end (scope, timelines, budgets, risk, and change management).
• AI fluency: understands common LLM-enabled use cases; can shape prompts/playbooks, evaluate quality at a basic level, and choose appropriate off-the-shelf tools or vendors.
• High proficiency with Google Workspace, Asana/Notion, Slack, and comfort with modern web and content tools; experience preparing polished executive documents and presentations.
• Bonus: familiarity with no/low-code automation (e.g., Zapier/Make), knowledge bases, and responsible AI considerations (privacy, data handling, consent).

• Mission-driven; systems thinker with bias for action.
• Clear, concise communicator; calm under pressure.
• Able to hold strategic context while driving tactical execution.

• Education: Bachelor’s degree or equivalent experience.
• Ethics: Commitment to ethical practices and responsible AI.
• Travel: Occasional (10–30%) for client activities and events.
• Location: Remote-friendly with preference for candidates in major tech hubs.

This role offers a competitive base salary with performance-based bonuses. Final compensation will vary based on experience, performance, and location.

Join a team of thinkers and builders creating meaningful impact across sectors—with autonomy to lead, the resources to succeed, and room to grow.

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