Top Chief Of Staff Jobs in Chicago, IL

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.

Serve as operational lead for the Chief Product Officer, translating strategy into execution, managing cross-functional program and product operations, building roadmaps, governance, executive communications, and driving accountability for major product launches and transformation initiatives.

Serve as CIOs trusted advisor to translate technology strategy into priorities, operating plans, and measurable outcomes. Own operating model, governance, and executive coordination. Lead cross-functional initiatives, separation readiness, KPIs and dashboards, financial and resource planning, and executive communications to ensure disciplined execution.

Serve as liaison between senior leadership and staff to drive strategic initiatives, oversee daily operations, track project deliverables, develop action plans, manage communications, and organize business-critical meetings while improving operational efficiency.

Partner with the CEO to own company metrics, operating cadence, and strategic initiative portfolio. Run board/investor materials and key workstreams, remove CEO bottlenecks, coordinate cross-functional launches (multi-state, compliance, vendor migrations), and occasionally lead functions until they have permanent leaders.

Serve as a high-impact executive partner to the President: manage inbox/Slack, calendar, meeting transcripts and action items, coordinate cross-functional projects, support onboarding/travel/board prep, and provide candid judgment to protect strategic time.

Act as the founders' right hand to operationalize AI: prototype internal AI workflows, turn experiments into company-wide programs, run executive cadence and OKRs, unblock cross-functional projects, prepare strategic briefs, enforce responsible AI guardrails, and drive exit-readiness and organizational health.

Senior strategic partner to the CCMO who drives cross-functional delivery, runs leadership cadence and governance, translates strategy into priorities, manages confidential high‑impact projects, shapes executive engagements, and ensures accountability across Brand, Communications, Marketing and Operations.

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.

Serve as the CLO's Chief of Staff and lead Legal Operations: manage a small team and global legal budget, own legal vendor and tech strategy (CLM, e-billing, litigation tools), build dashboards and metrics, drive cross-functional integration, and implement AI-driven automation to improve reporting, decision-making, and operational efficiency across legal, corporate development, and IT.

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.

The Chief of Staff / Integrator will manage operations for two eCommerce brands, driving execution, improving workflows, and building operational systems to support growth.

Drive strategic execution for the AI Neobank: build operating rhythms, manage OKRs, coordinate cross-functional workstreams, prepare leadership/board materials, identify and mitigate risks, support trade-offs and special projects requiring senior judgment and cross-functional authority.

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

Partner with the CEO to drive strategic initiatives, prepare board and executive materials, support budgeting and performance reporting, build dashboards, analyze SaaS metrics, and coordinate cross-functional execution to improve organizational effectiveness.

The Chief of Staff will work closely with the CEO and leadership team to drive company-wide execution, oversee strategic initiatives, improve processes across teams, and lead critical projects to accelerate growth and patient impact.

Partner with the CEO/COO to translate strategy into execution, build AI-enabled operating systems, drive cross-functional programs, run OKRs and planning cadences, scale vendor/procurement, and lead high-priority projects end-to-end.

Lead technical direction for program engineering across hardware, software, and firmware. Act as technical advisor to the program manager, coordinate multidisciplinary teams, ensure adherence to engineering processes, drive design, development, implementation, testing, and delivery, and produce technical presentations. Maintain required security clearance and collaborate through EMD/LRIP phases to field defense systems.

Owns technical direction for program engineering across design, development, implementation, testing and delivery. Serves as technical leader and advisor to the program manager, coordinating multidisciplinary teams, ensuring engineering process compliance, and supporting systems integration and test for hardware, software, and firmware.

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

Deputy to the Chief Engineer responsible for leading engineering personnel, planning and executing maintenance and repairs, managing spares and fuel operations, ensuring environmental compliance, supporting safety investigations, and maintaining the shipboard management system and risk assessments.

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 right hand to the Head of Sales, running sales cadence, driving pipeline visibility and forecasting, enabling reps with materials, coordinating cross-functional GTM work, structuring strategic problems, supporting hiring/onboarding, and preparing executive-level communications to improve sales execution and accountability.

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.