Chief of Staff

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.

About the role

The Chief of Staff serves as the connective tissue driving accountability across operations (including 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. Success in this role is defined less by the specific subject matter in front of this person on any given day 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 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.

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, researching, presenting, and implementing 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.

Requirements

• 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.

Skills

• 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.

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.

Pay

Base salary: $250,000 to $400,000 + performance bonus, depending on experience.

Schedule

Fully onsite in Chicago, IL, 5 days per week. Travel is not expected on an ongoing basis; some initial travel to the family's other properties may be required to build relationships with teams.