Strategic Chief of Staff — Growth, Governance & Execution

Windsor Advantage, LLC; Chicago (IL); Hybrid; USD 125,000 - 165,000; Full time

Benefits offered by this job

Comprehensive benefits package

Company-paid health benefits

401(k) with company contributions

Paid time off and holidays

Tuition reimbursement program

Job summary

Windsor Advantage LLC in Chicago seeks a Chief of Staff to act as the President's strategic extension, coordinating governance, risk, and ongoing strategic initiatives. You will drive leadership alignment, oversee reporting, and coordinate with ownership and shared-service partners to advance priorities.

The role requires a Bachelor's degree and a track record of guiding cross-functional programs, with compensation reflecting senior leadership responsibilities and a robust benefits package.

Qualifications

• Bachelor's degree or equivalent combination of education and relevant professional experience required.
• Experience supporting executive leadership in a dynamic, growth-oriented organization.
• Demonstrated experience leading cross-functional initiatives and driving organizational accountability.
• Exposure to financial reporting, operations, compliance, risk management, governance, audits, or related business functions.

Responsibilities

• Serve as the President's strategic extension, driving execution of organizational priorities and increasing leadership capacity across the business.
• Administer Windsor's operating cadence, including leadership meetings, organizational reporting, decision tracking, and executive accountability.
• Act as the primary liaison between Windsor, its ownership, affiliates, and shared-service partners, ensuring alignment on strategic, governance, compliance, and risk initiatives.
• Lead Board and ownership reporting activities, including preparation of executive narratives, performance reporting, governance materials, and policy oversight.
• Oversee accounting and financial reporting processes, including month-end close governance, financial reporting review, budgeting coordination, and executive decision support.
• Direct enterprise compliance, risk management, audit, examination, business continuity, vendor management, and related governance activities through coordination with internal and external stakeholders.
• Provide executive leadership on organizational change, process improvement, policy development, and operational scalability initiatives.
• Coordinate cross-functional execution of strategic priorities, ensuring alignment, accountability, and effective escalation of significant business issues.
• Maintain enterprise-level visibility into operational, financial, compliance, and strategic risks, providing recommendations and escalation to executive leadership as appropriate.
• Build and maintain trusted relationships with internal leaders, ownership groups, clients, regulators, auditors, and strategic partners.

Skills

Strategic thinking

Leadership

Cross-functional collaboration

Executive communication

Stakeholder management

Analytical capabilities

Organizational planning

Education

Bachelor's degree or equivalent

Job description

Windsor Advantage LLC in Chicago seeks a Chief of Staff to act as the President's strategic extension, coordinating governance, risk, and ongoing strategic initiatives. You will drive leadership alignment, oversee reporting, and coordinate with ownership and shared-service partners to advance priorities.

The role requires a Bachelor's degree and a track record of guiding cross-functional programs, with compensation reflecting senior leadership responsibilities and a robust benefits package.