Chief of Staff

Windsor Advantage • Chicago, IL

6d • $125,000 - $165,000 • 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 ownership and shared-services partners on compliance, risk, audit, and governance matters. Working across departments without direct authority over functional leaders, the position relies on judgment, influence, disciplined follow-through, and clear escalation to advance organizational priorities.

The role supports organizational change, process improvement, policy development, operational scalability, and enterprise-level decision-making. It also builds and maintains relationships with internal leaders, ownership groups, clients, regulators, auditors, and strategic partners, and takes on additional leadership responsibilities and special projects as assigned.

Requirements

• Bachelor’s degree or an equivalent combination of education and relevant professional experience.
• 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 ability to manage confidential and executive-level matters.
• Strong analytical, planning, and decision-making capabilities, including synthesizing complex financial, operational, compliance, and risk information into actionable recommendations.
• Exceptional organizational skills, attention to detail, and follow-through, with the ability to independently manage multiple priorities and deadlines.
• Executive presence and strong 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 demonstrated ability to lead and support organizational change.
• Working knowledge of government-guaranteed lending products, compliance requirements, and operational processes.

Nice To Haves

• Experience in banking, lending, accounting, consulting, operations, compliance, risk management, or a Chief of Staff capacity.
• Banking experience.
• Advanced knowledge of government-guaranteed lending products, compliance requirements, and operational processes.

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, including 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; provide recommendations and escalate issues 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 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 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.

Benefits

• Comprehensive benefits package including medical, dental, vision, company-paid life insurance, and disability insurance.
• Company contributions to a 401(k), regardless of employee contribution.
• Paid parental leave.
• Employee recognition program.
• Leadership program.
• Tuition reimbursement program.
• Employee bank checking account.
• Generous paid time off and paid holidays.
• Paid charity hours to support volunteer opportunities.
• Yearly annual target bonus based on individual performance.

What This Job Offers

• Job Type: Full-time
• Career Level: Senior