The Chief of Staff Association has been retained by a single-family office to identify the Chief of Staff to the Principal.
The family office's interests span private aviation operations, a luxury residential and hospitality portfolio, and direct investments in operating businesses and entrepreneurial ventures. The Principal is increasingly focused on growing the entrepreneurial and business creation side of the organization, while the Chief of Staff will lead day to day operations across the businesses and spearheads the entrepreneurial side.
Chief of Staff Role
The Chief of Staff serves as the connective tissue driving accountability across operations (including, but not limited to office administration, PR, HR, security, aviation, household and personal residences, all staffing, and vendor/outsourced resource management). In many ways, this person operates as a de facto COO. In parallel, this role serves as a strategic partner and thought partner to the Principal, translating his vision into action across a wide range of special projects, entrepreneurial initiatives, and ambiguous problems. This is a high trust, high discretion environment. The right individual will bring structure, operate with sound judgement, and move fluidly between strategic priorities and hands on execution.
Above all, the principal is looking for a brilliant problem solver: someone with exceptional judgement, raw intelligence, and the ability to work through unfamiliar situations with limited direction. Specific family office pedigree matters less than the demonstrated capacity to learn quickly, connect the dots across a wide range of challenges, from special projects and new ventures to operations, and drive a problem through to resolution once a plan is set. This person will regularly be handed an outcome to solve for, rather than a defined process to follow, and needs the intellectual horsepower to build the plan of attack themselves. We are looking for a genuinely brilliant operator with sound judgement and strong problem solving instincts.
Success in this role is defined less by the specific subject matter in front of this person on any given day, whether that is a new venture idea, a vendor dispute, or a special project with no obvious owner, and more by how they think: the ability to create clarity in ambiguous environments, exercise sound judgement under pressure, and drive disciplined execution across a wide and constantly shifting set of priorities. This person will also hold team leaders accountable across every operating division, enabling the Principal to focus on strategic growth rather than day to day management.
This role requires the ability to operate as a filter and amplifier for the principal, ensuring their time and attention are protected and deployed against the highest value priorities, while proactively resolving operational friction before it reaches senior leadership.
This will be a full time position based fully onsite in Chicago, IL.
Responsibilities
Operational Leadership & Accountability
Serve as the management layer and connective tissue between the principal, the CEO, and the teams running day to day operations, reducing the operational friction currently absorbed by senior leadership.
Hold team leaders accountable across every operating division outside of investments and financials, addressing performance gaps constructively and driving issues to resolution before they reach the principal.
Own the HR function across operating teams, including proactively identifying and addressing performance and conduct issues before they escalate.
Strategic Initiatives & Special Projects
Partner directly with the Principal to execute on his vision for business incubation, helping translate early-stage ideas for new ventures into actionable plans and driving them from concept through launch.
Support the Principal's charitable and philanthropic priorities, including researching causes, building relationships with nonprofit partners, and helping structure giving initiatives.
Track progress against milestones across active ventures, flagging risks and reporting status regularly to the Principal.
Act as a proactive problem solver when presented with an unfamiliar or ambiguous issue, research, present, and implement solutions, bringing a plan of attack rather than simply escalating.
Act as a C-suite level thought partner, building the organizational structure and systems needed to support the family office's next stage of growth.
Team & Vendor Management
Directly oversee the aviation team, ensuring precise, proactive, and consistent communication of the principal's travel logistics.
Oversee household staff and vendor relationships across the family office's properties.
Manage staffing challenges by building trust and consistency with vendors and staff while holding them to high standards of service.
Bring the discipline and direct communication style needed to give team leaders clear direction.
Standards, Systems & Documentation
Develop and implement consistent standards and protocols across every operating division (aviation, household, staffing, and vendor management).
Build documentation and systems, such as estate manuals, digital SOPs, and operational playbooks, to formalize institutional knowledge and improve consistency.
Improve internal coordination and communication across all teams to ensure efficient decision making and execution.
Maintain high standards of organization, discretion, and follow-through across all responsibilities.
Minimum Qualifications
Demonstrated exceptional judgement, raw intelligence, and problem solving ability, evidenced through academic achievement, professional track record, or a demonstrated history of succeeding in unfamiliar or high ambiguity situations.
Chief of Staff experience in a corporate business environment is strongly desired.
Bachelor's degree required; an advanced or graduate degree is valued but not required.
Demonstrated experience helping a founder or principal build organizational infrastructure such as people systems, operating cadence, and cross-functional accountability.
Demonstrated ability to hold team leaders and vendors accountable, manage HR-related conflict, and drive issues to resolution with a direct approach.
Excellent written and verbal communication skills with strong executive presence and high EQ.
Preferred Skills & Attributes
High judgement and discretion in sensitive financial and personal matters, in a high trust household.
Low ego, high ownership individual who can move fluidly between strategic thought partnership and hands on execution.
High EQ with the ability to navigate nuanced interpersonal and organizational dynamics, while being direct when needed and maintaining strong working relationships.
Comfortable giving clear, sometimes difficult, direction to staff and vendors in order to protect the principal's time and enforce standards.
Compensation & Logistics
Base Salary: $250,000 to $400,000 + performance bonus, DOE.
Location: Chicago, IL, fully onsite 5 days/week.
Travel: not expected on an ongoing basis; some initial travel to the family's other properties to build relationships with teams.
Benefits: medical, dental and vision coverage, with a choice of plan options and 90 percent of the employee premiums covered by the company; 401(k) retirement plan with a company match after 12 months of service; healthcare, dependent care, and commuter/parking flexible spending accounts.
Why Work for Our Client?
Build something new: join a Principal who is actively building an entrepreneurial family office, not simply overseeing an existing portfolio, with the opportunity to shape new ventures alongside the core operating businesses.
High caliber team: work alongside a Principal who is actively raising the bar on talent across the organization, most recently reflected in a senior finance hire without prior family office background who has quickly become a standout performer.
Real ownership: step into a role explicitly designed to be a genuine COO-level position rather than a high-level assistant role, with every operating division reporting up through this seat.
Variety and scale: engage with a wide range of challenges across aviation, household operations, HR, PR, and entrepreneurial ventures spanning multiple markets
What to Expect from Our Selection Process
The selection process is designed to assess judgement, problem solving ability, executive presence, and cultural fit, ensuring a strong mutual fit for both you and the family office. The process includes:
The Chief of Staff Association Predictive Index Assessment
The Chief of Staff Association Screening: 15 minute phone interview and 30 minute video interview
Virtual Interview with the Principal
Case Study
In-Person Case Study Debrief, plus a meeting with another influential leader within the organization
Final Interview: multi-day, in-person with the Principal and the Leadership Team
Note: The Chief of Staff Association partners with The Predictive Index to align workstyles with the role. All applicants complete this quick, two-question, five-minute assessment—no right or wrong answers—and receive a profile readout.
- -> Please take the assessment here as you complete your application.
Our client 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.
