Chief of Staff - Chicago, IL

Human Agency•Chicago, IL

11d•Remote

About The Position

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.

Requirements

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.
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.

Nice To Haves

Familiarity with no/low-code automation (e.g., Zapier/Make), knowledge bases, and responsible AI considerations (privacy, data handling, consent).

Responsibilities

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.