Chief of Staff

Be the right hand to the President of a full-service Chicago family office: a new, long-term Chief of Staff seat uniting a collegial team to serve a rising generation. Hybrid, four days on-site.

The Chief of Staff Association has been retained by a single-family office in the Chicago area to identify the Chief of Staff to the President.

The family office provides full-service support to the first and second generations of a multi-generational business family, including investment advisory, tax, legal, trust and estate planning, insurance and risk, financial accounting and reporting, and residential services. The office has grown steadily in recent years and continues to evolve its capabilities as the needs of the family expand.

Chief of Staff Role

The Chief of Staff to the President will serve as a strategic partner, trusted advisor and execution leader within a complex, multi-generational family office environment. Reporting to the President, this newly created role will support the coordination and advancement of key priorities across all departments, family-facing matters and special projects.

The Chief of Staff will help translate strategic objectives into actionable plans, drive follow-through on key initiatives, prepare executive-level analysis and presentations, and ensure clear communication and accountability across internal teams, family members and external advisors. A central part of the role is strengthening integration across the office's functions, so that the investment, tax, legal, trust and estate, and accounting teams work in a coordinated way on behalf of the family.

The successful candidate will combine strong business and financial acumen with exceptional judgment, analytical capability, discretion and service orientation. The ideal candidate will be polished, proactive, highly organized and technically savvy, with the emotional intelligence to build trust across a close-knit team and the composure to navigate sensitive conversations. They will be comfortable operating in both strategic and hands-on capacities.

Success in this role means the President is able to focus on strategic priorities, cross-functional initiatives are delivered with clear ownership and follow-through, and the family experiences the office as a cohesive and responsive partner.

This is a full-time position based in Chicago's northwest suburbs, with four days per week in the office and one remote day.

Responsibilities

Strategic Planning & Executive Support

Serve as a strategic thought partner to the President on organizational priorities, business initiatives and family office objectives.

Support the development, communication and execution of strategic initiatives, long-term plans and key organizational priorities.

Prepare the President for meetings, presentations, family discussions and planning sessions through thoughtful briefing materials and decision support.

Track priorities, deliverables and action items to ensure accountability, timely execution and effective follow-through.

Coordinate cross-functional projects involving internal teams, family members, external advisors, vendors and other stakeholders.

Develop project plans, timelines, status updates and reporting mechanisms for the President that support clarity, ownership and execution.

Monitor progress, resolve obstacles and ensure initiatives remain aligned with the President's priorities and the office's broader objectives.

Family & Stakeholder Relationship Management

Serve as a trusted liaison among the President, family members, senior leaders, employees and external advisors.

Facilitate clear, timely and professional communication across stakeholders while promoting alignment and responsiveness.

Build strong relationships and operate with a client-service mindset in all family-facing and stakeholder interactions.

Business Analysis, Communications & Presentation Development

Analyze operational, financial and organizational information to identify trends, risks, opportunities and actionable insights.

Prepare executive summaries, reports, dashboards, briefing documents and business cases to support informed decision-making.

Develop clear, compelling and polished PowerPoint presentations and other executive materials for varied audiences.

Translate complex information into concise, practical recommendations and professional written communications.

Technology, Innovation & Process Improvement

Leverage technology, automation, artificial intelligence and Microsoft-based tools to improve productivity, reporting, communication and organizational effectiveness.

Identify opportunities to streamline workflows, improve collaboration, enhance reporting and strengthen processes.

Partner with stakeholders to evaluate systems, tools and process improvements that support the continued evolution of the family office.

Operational Partnership & Continuous Improvement

Partner with leadership and cross-functional teams to identify needs, resolve issues and support continuous improvement.

Promote accountability, responsiveness, collaboration, innovation and service excellence across the organization.

Demonstrate sound judgment, discretion and professionalism in handling sensitive financial, operational, family and personnel matters.

Minimum Qualifications

Bachelor's degree in business administration, finance, accounting, economics, management or a related field required.

8+ years of experience in a family office, private investment, consulting, corporate strategy, finance, operations, executive office or related environment.

Demonstrated experience supporting senior executives, business owners, principals or C-suite leaders in a high-trust, confidential environment.

Strong business and financial acumen, including the ability to interpret financial information, assess business implications and prepare decision-useful analysis.

Exceptional analytical, problem-solving, project management, organizational, interpersonal and communication skills.

Demonstrated ability to prepare polished executive presentations, reports, business cases, briefing materials and strategic recommendations.

Advanced proficiency in Microsoft Office, including PowerPoint, Excel, Word, Outlook and Teams, with a demonstrated ability to present information visually and effectively.

Strong technical aptitude, including experience using AI tools, automation, collaboration platforms and emerging technologies to improve productivity and outcomes.

Demonstrated ability to communicate professionally and effectively with family members, senior leadership, employees and external advisors.

High degree of integrity, discretion, judgment and professionalism, with the ability to operate effectively in a highly confidential environment.

Strong attention to detail, ownership mindset, urgency, responsiveness and commitment to producing high-quality work.

Preferred Skills & Attributes

Experience in a family office.

Experience supporting client-facing matters, executive communications, governance processes or cross-functional strategic initiatives.

Experience with dashboards, business intelligence tools, project management platforms or workflow automation tools.

Experience with Sage Intacct or a comparable cloud-based accounting platform, and Addepar or a comparable cloud-based portfolio platform.

High emotional intelligence and a collaborative, service-oriented approach, with a track record of building trust and long-term working relationships.

Compensation & Logistics

Base Salary: $200,000 to $250,000 + 20% bonus, DOE.

Location: Chicago's northwest suburbs; four days per week in the office and one remote day, with five days per week in the office during onboarding.

Travel: not expected.

Benefits: competitive benefits package, including a 401(k) retirement plan.

Why Work for Our Client?

Long-term opportunity: a newly created role partnering directly with a President who brings nearly 30 years of family office leadership experience.

Breadth of exposure: involvement across every function of a full-service family office, including investments, tax, legal, trust and estate, financial accounting and residential services.

Meaningful impact: the opportunity to shape how the office serves a rising generation of family members and to strengthen integration across its teams.

Collaborative culture: a considerate, driven and collegial team committed to continuous improvement and service excellence.

Stability: a well-established office with the full support of the family and a competitive total compensation package.

What to Expect from Our Selection Process

The selection process is designed to assess judgment, business and financial acumen, executive communication and cultural fit, ensuring a strong mutual fit for both you and the family office. The process includes:

The Chief of Staff Association Screening: 15 minute phone interview and 30 minute video interview, plus The Chief of Staff Association Predictive Index Assessment

Execution of a Non-Disclosure Agreement prior to the family office's name being shared

Virtual Interview with the Senior Director of Operations and Human Resources

Virtual Interview with the President

Final Interview: in person with the President and members of the Senior Leadership Team, including situational case study scenarios

The Chief of Staff Association is committed to creating and maintaining a diverse and inclusive workplace where our employees can thrive and be themselves. We welcome all persons into our community. We embrace the diversity of gender, gender identity or expression, race, color, religious creed, national origin, ancestry, age, physical and mental disabilities, medical condition, genetic characteristic, sexual orientation, marital status, family care or medical leave status, military or veteran status, or perceived membership in any of these groups.