Chief of Staff Greater Chicago, IL Area

About Us

Windsor Advantage, an affiliate of Capital Bank N.A., is one of the nation's leading Lender Service Providers (LSP). Windsor Advantage provides banks, credit unions and CDFIs with a comprehensive outsourced SBA 7(a) and USDA lending platform without the need to hire staff or incurring capital expenditures. Since 2010, Windsor has processed more than $4.5 billion in government guaranteed loans and currently services a portfolio for over 100 lenders nationwide.

With more than 150 years of cumulative SBA lending experience, cutting edge technology, rigid controls and consistent processes, Windsor is uniquely qualified to assist any size lender with implementing a thoughtful and profitable government guaranteed lending initiative.

Capital Bank N.A. is headquartered in Maryland and has been serving our communities since 1999. We stand as a publicly traded company (NASDAQ: CBNK) with over $3 billion in assets. We offer commercial and consumer banking services primarily to clients in Maryland, DC, and Northern Virginia, alongside two nation-wide lending brands; Capital Bank Home Loans and OpenSky, a credit card division that offers and services credit cards across all states.

Position Purpose

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.

Position 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.

Additional Responsibilities

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.

Minimum Education & Experience

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.

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.

No specific professional credentials are required.

Technical Knowledge and Skills

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.

Working knowledge of government-guaranteed lending products, compliance requirements, and operational processes; advanced knowledge preferred.

Compensation

Base Salary Range: $125,000 - $165,000 annually. Final determination of where you are at in the salary range is based on numerous factors such as geographical location, relevant experience, skill set, education, and ability to meet qualifications within the job description.

Additional Compensation: This role will include a yearly annual target bonus based on individual performance.

Working Arrangements

This is a hybrid role expected to work in office Monday, Wednesday, and Thursday. You will be able to work remotely on Tuesday and Friday– Chicago Office

Why Join Us?

Join a growing company with a culture that fosters an entrepreneurial spirit

Comprehensive benefits package including Medical, Dental, Vision, Company Paid Life Insurance, Disability Insurance, and more?

Company Contributions to your 401k - Regardless of your contribution

Employee Perks: Paid Parental Leave, Employee Recognition Program, Leadership Program, Tuition Reimbursement Program, Employee Bank Checking Account, and much more!

Generous Paid Time Off and Paid Holidays - Including Paid Charity Hours to support volunteer opportunities

Supporting Businesses. Helping People. Strengthening Communities.

Windsor Advantage LLC is an E-Verify, Affirmative Action and Equal Opportunity Employer.

Supporting Businesses. Helping People. Strengthening Communities.

Windsor Advantage LLC is an E-Verify, Affirmative Action and Equal Opportunity Employer.