Chief of Staff

Windsor Advantage•Chicago, IL

4d•Hybrid

About The Position

The Chief of Staff serves as the President’s strategic extension and organizational integrator, increasing executive capacity and strengthening coordination across Windsor Advantage. The role administers the company’s operating cadence, drives cross-functional follow-through, oversees accounting and financial reporting coordination, and connects Windsor with its ownership and shared-services partners on compliance, risk, audit, and governance matters. The position works across departments without direct authority over functional leaders and relies on judgment, influence, disciplined follow-through, and clear escalation to advance organizational priorities. The role also supports organizational development, succession planning, talent initiatives, leadership effectiveness, strategic projects, and the development of policies and operational standards. It requires working knowledge of Windsor’s business lines and operational functions to support enterprise-level decisions and alignment.

Requirements

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, managing competing priorities, and driving organizational accountability.
Exposure to financial reporting, operations, compliance, risk management, governance, audits, or related business functions.
Sound judgment, discretion, and the ability to manage confidential and executive-level matters.
Strong analytical, planning, and decision-making capabilities, including the ability to synthesize complex financial, operational, compliance, and risk information into actionable recommendations.
Exceptional organizational skills, attention to detail, and follow-through, with the ability to manage multiple priorities and deadlines independently.
Executive presence and outstanding written, verbal, presentation, and stakeholder-management skills.
Ability to influence, coordinate, and drive accountability across functions without direct authority.
Strong leadership, relationship-building, and internal customer service skills.
Adaptability, intellectual curiosity, and a demonstrated ability to lead and support organizational change.

Nice To Haves

Experience in banking, lending, accounting, consulting, operations, compliance, risk management, or a Chief of Staff capacity is preferred.
Banking experience is preferred; prior SBA, USDA, or government-guaranteed lending experience is not required.
Working knowledge of government-guaranteed lending products, compliance requirements, and operational processes; advanced knowledge preferred.

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 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.
Support executive leadership in organizational development, succession planning, talent initiatives, and leadership effectiveness.
Lead or coordinate assigned strategic initiatives and special projects on behalf of the President.
Develop and maintain policies, procedures, governance documentation, and operational standards that support scalable growth.
Coordinate due diligence, examinations, audits, and remediation activities with internal teams, ownership, and external stakeholders.
Develop a working knowledge of all Windsor business lines and operational functions to support enterprise-level decision-making and organizational alignment.
Perform other duties and leadership responsibilities as assigned in support of evolving business objectives.