Top Chief Of Staff Jobs in Chicago, IL

Partner with the CEO to translate strategy into executable plans, lead high-priority cross-functional initiatives, monitor business metrics, synthesize insights for decision-making, and coordinate across merchandising, marketing, e-commerce, operations, finance, and retail/wholesale partners.

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.

Oversee operations and coordinate projects within engineering, acting as a liaison between management and engineers, providing technical support, and maintaining developer documentation.

The Chief of Staff to the CEO will manage the company's operating system, drive strategic projects, facilitate communication, and align leadership priorities with a strong commitment to healthcare access.

The Chief of Staff assists the CEO with high-priority initiatives, driving execution, increasing operational efficiency, and ensuring effective communication within the company.

Partner with the COO to lead and execute firmwide strategic initiatives, run operating cadence, prepare executive and Board materials, build operational infrastructure, and drive AI adoption and governance across the business.

Serve as the CEO's strategic and operational right hand at an AI LegalTech startup: prepare executive/board/investor materials, build financial models and decks, contribute litigation expertise to product content, validate LLM-generated analyses, drive cross-functional execution, manage company operations (recruiting, vendor administration, OKRs), represent the CEO, and handle special projects across finance, legal, and partnerships.

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 VP of Operations and executive team to turn strategy into execution: run company planning (OKRs), operating cadence, KPIs, SOC 2 readiness, acquisition integration, investor/vendor relations, recruiting loops, and cross-functional initiatives while driving AI adoption and scaling processes.

Serve as the executive owner for AI transformation at mid-market clients: convene and facilitate C-suite AI steering committees, build board-ready AI roadmaps tied to KPIs and ROI, coordinate delivery teams, unblock workstreams, surface expansion opportunities, and refine the AI Chief of Staff playbook to scale Pragmatico’s offerings.

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

The Staff Chief Engineer oversees engineering operations on the luxury yacht Amangati, ensuring compliance, safety, and high standards of technical performance during construction and operational phases.

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

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.

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.