Top Chief Of Staff Jobs in Chicago, IL

Serves as a strategic partner to founders and executives by managing priorities, filtering decisions, translating vision into organizational action, preparing high-stakes meetings, synthesizing business reporting, coordinating stakeholders, identifying risks, supporting planning and resource allocation, drafting executive communications, managing confidential information, and leading special projects. The role also owns client satisfaction and evaluates whether engagements continue to meet evolving executive needs.

Drives major priorities and cross-functional projects across ActAI’s businesses from decision through execution. Identifies and solves business problems, tracks performance and ownership, leads expansion and organizational initiatives, analyzes markets and financials, and coordinates across product, technology, finance, people, and operations.

Serve as a strategic advisor and operational partner to the CEO, driving executive operating cadence, cross-functional strategy execution, transformation initiatives, and executive communications. Lead enterprise initiatives, develop executive materials and dashboards, remove execution barriers, and implement AI-enabled workflows to increase CEO leverage and organizational alignment.

The Chief of Staff will partner with the co-founder and leadership team to scale internal operations across a rapidly growing philanthropic organization. Responsibilities include running OKRs, KPI dashboards, operating rhythms, leadership meetings, decision-making processes, internal systems, AI-enabled tooling, communication norms, knowledge management, strategic initiatives, and occasional partner support. The role requires proactive problem-solving, strong execution, clear communication, comfort with ambiguity, and approximately seven or more years of relevant experience.

The Chief of Staff will lead AI transformation projects, manage investment funds, drive sales initiatives, and oversee client project delivery, requiring self-direction and proactivity.

The Chief of Staff will oversee operational projects, refine strategies, and support leadership in a fast-paced scaling environment.

Support the executive by cutting administrative workload 50% within 30 days, convert tribal knowledge into SOPs, manage weekly/6-month/2-year OKRs and org chart, configure productivity tools, proactively solve problems, and ensure clear, error-free communication across teams.

Serve as a strategic operator and force multiplier for the CEO and leadership team. Drive cross-functional initiatives, prepare Board and investor materials, enable AI adoption and build workflows, support finance and revenue analytics, coordinate leadership rhythms and company offsites, and translate executive priorities into measurable plans and follow-through.

The Chief of Staff partners with executive leadership to operationalize firm-wide strategy, coordinate cross-functional initiatives, manage capacity planning, oversee performance metrics, and improve leadership effectiveness. Responsibilities include facilitating executive meetings, supervising senior staff, coordinating proposal pipelines, aligning recruiting and resource plans with business development, managing organizational dashboards, supporting client and partner engagement, and leading internal communications and culture initiatives. The role is remote within the U.S. with approximately 10–15% travel.

Leads strategic and operational execution for an international professional association. Responsibilities include membership growth and retention, CRM and data governance, marketing automation, performance reporting, budgeting, volunteer engagement, staff leadership, and board support. The role aligns organizational priorities, improves systems and workflows, strengthens financial performance, and enhances member value.

The Chief of Staff will support the Managing Director of AI, leading AI transformation initiatives, designing automated systems, and ensuring successful delivery across multiple client projects.

Coach and mentor clients pursuing chief of staff and executive support roles. Teach strategic planning, executive support, and AI fundamentals/automation. Provide career guidance including resume, LinkedIn, cover letters, interview prep, networking, salary negotiation, and promotion strategy. Host virtual sessions on flexible schedule and collaborate with Leland team to ensure high-quality client outcomes.

Lead operational rhythms and client delivery, focusing on AI solutions. Collaborate with executives and manage multi-stakeholder projects for positive outcomes.

The Chief of Staff supports the Chairman by driving strategic initiatives, managing projects, and optimizing decision-making processes while ensuring operational efficiency across ventures.

Serve as the SVP's right hand for Healthcare Analytics by managing budgets and ROI, running operational rhythms (recruiting, onboarding, meetings), producing executive communications, supporting strategic planning and talent processes, coordinating cross-functionally, and resolving blockers to ensure delivery and alignment.

The Chief of Staff will lead operational projects, ensuring delivery of AI solutions, managing client relations, and coordinating cross-functional efforts for success.

Serve as the associationhief Staff Officer overseeing membership growth, operations, CRM/data strategy, digital marketing, education programming, volunteer governance, financial oversight, and staff leadership to drive engagement and operational excellence.