Position Overview
We are seeking a highly sophisticated, discreet, organized, and proactive Executive Assistant to support the CEO of
a diversified investment and operating enterprise.
The CEO is an investment banking attorney and business owner with responsibilities spanning investment banking
and M&A advisory, legal and transactional matters, restaurant and hospitality operations, healthcare practices,
commercial real estate, and manufacturing.
This is not a traditional administrative assistant position. The successful candidate will operate as a trusted
extension of the CEO, managing a highly dynamic schedule, coordinating business and personal priorities,
preparing for meetings, tracking transactions and initiatives, and ensuring that commitments across multiple
companies and professional relationships are executed efficiently.
Key Responsibilities
Executive Support
- Manage and strategically prioritize the CEO's complex calendar, meetings, travel, calls, and appointments.
- Serve as a primary gatekeeper and point of contact for clients, attorneys, bankers, investors, executives,
vendors, and business partners.
- Prepare the CEO for meetings by organizing agendas, background materials, financial information,
correspondence, and follow-up items.
- Maintain a comprehensive system for tracking commitments, deadlines, deliverables, and outstanding
matters.
- Anticipate the CEO's needs and proactively address issues before they become problems.
- Coordinate domestic and international travel, including flights, hotels, ground transportation, itineraries, and
business meetings.
Investment Banking & Legal Support
- Assist with confidential M&A transactions, acquisitions, divestitures, financing activities, and due diligence.
- Organize transaction documents, correspondence, financial information, and deal timelines.
- Coordinate communications among attorneys, accountants, investment bankers, lenders, investors, brokers,
and counterparties.
- Prepare meeting materials, summaries, presentations, and transaction status reports.
- Track legal and corporate deadlines and ensure appropriate parties are reminded of outstanding matters.
- Maintain strict confidentiality regarding client, financial, legal, and transactional information.
Portfolio Company Support
The Executive Assistant will interact with leadership across multiple operating businesses, including:
- Restaurant and hospitality operations
- Healthcare practices
- Real estate holdings and development
- Manufacturing operations
- Investment banking and advisory activities
Responsibilities may include coordinating executive meetings, collecting operating reports, following up with
management teams, scheduling site visits, tracking action items, and ensuring information reaches the CEO in a
timely and organized manner.
Business & Financial Administration
- Assist with preparation and organization of financial reports, P&Ls, investment materials, budgets, and
operating reports.
- Maintain executive-level dashboards and lists of active projects and transactions.
- Coordinate with accounting, finance, legal, HR, and operations teams.
- Assist with research and preparation of executive briefings.
- Monitor important correspondence and ensure timely responses or delegation.
Communications
- Draft, proofread, and format executive correspondence, emails, letters, memoranda, and presentations.
- Communicate professionally with sophisticated business executives, attorneys, financial institutions,
government officials, vendors, and clients.
- Manage sensitive communications with appropriate judgment regarding what should be escalated directly to
the CEO.
Executive & Personal Lifestyle Support
- Develop a detailed understanding of the CEO's routines, preferences, habits, and working style and use that
knowledge to anticipate needs without requiring repeated instruction.
- Learn and consistently apply the CEO's preferred hotel brands, room preferences, airline and travel seating
preferences, transportation preferences, and other travel-related requirements when planning or coordinating
travel.
- Maintain the CEO's high organizational standards, including specific expectations regarding order, cleanliness,
organization, and germ-conscious environments. These are personal organizational and cleanliness
preferences and should not be interpreted as a representation of a medically diagnosed condition.
- Provide appropriate personal-life assistance, including coordination of personal appointments, reservations,
household or family-related logistics, errands, and other administrative matters, with the objective of reducing
nonessential demands on the CEO's time and allowing greater availability for his children and family.
- Maintain awareness of and accommodate the CEO's personal dietary and environmental requirements,
including a shellfish allergy, dust-mite allergy, and a dietary restriction against pork. These requirements should
be considered when coordinating restaurants, catering, hotels, travel, meeting environments, and other
arrangements.
- Exercise exceptional discretion when handling personal, family, financial, legal, travel, and business
information.
- Accompany the CEO on certain domestic and/or international business travel, estimated at approximately 10%
travel, including assisting with itineraries, meetings, logistics, and schedule management while traveling.
- This is an in-person position based in the northern suburbs of Chicago and requires regular physical presence;
it is not intended to be a remote executive-assistant role.
Candidate Profile
The ideal candidate is:
- Exceptionally organized with strong attention to detail.
- Highly discreet and capable of handling confidential financial, legal, corporate, and personal information.
- Intelligent, polished, professional, and comfortable operating in executive environments.
- Extremely responsive and capable of managing competing priorities.
- A strong writer and communicator.
- Comfortable interacting with attorneys, bankers, investors, physicians, franchise operators, executives, and
high-net-worth individuals.
- Able to work independently without requiring constant direction.
- Comfortable with ambiguity and rapidly changing priorities.
- Technologically proficient and capable of learning new systems quickly.
- Someone who naturally thinks two or three steps ahead, learns the CEO's preferences and patterns over time,
and anticipates needs before being asked.
Preferred Qualifications
- 5+ years of experience supporting a CEO, Managing Partner, Founder, attorney, investment banker, private
equity executive, or other senior executive.
- Experience in investment banking, private equity, M&A, law, commercial real estate, healthcare, hospitality, or
other sophisticated professional environments preferred.
- Bachelor's degree in Finance or Accounting preferred.
- Exceptional Microsoft Office/Google Workspace skills, particularly Outlook, Excel, Word, PowerPoint, and
calendar-management platforms.
- Experience handling confidential documents and executive-level correspondence.
- Strong project-management and organizational capabilities.
Additional Role Requirements
- Ability and willingness to work in person in the northern suburbs of Chicago.
- Ability and willingness to travel with the CEO approximately 10% of the time, including domestic and/or
international travel as business needs require.
- Flexibility to support occasional personal or family-related administrative matters when necessary to protect
the CEO's time and schedule.
What Success Looks Like
The successful candidate will become the organizational hub of the CEO's professional life.
You will ensure that the CEO knows:
- What is happening
- What requires attention
- Who owes something
- What is due and when
- Which meetings require preparation
- Which issues need escalation
- What should happen next
The goal is not simply to manage the CEO's calendar—it is to create leverage for the CEO by allowing him to focus
his time on investment decisions, transactions, legal matters, business development, and strategic leadership.
Compensation
Hourly Compensation
$21.00-$35.00 per hour, commensurate with experience, education, qualifications, and demonstrated ability to
perform the responsibilities of the position.
Benefits
- Major medical insurance
- Dental insurance
- Hearing benefits
- Vision insurance
- 401(k) retirement plan
- Paid sick days
- Paid vacation
Ideal Candidate: Someone who views the position as a career opportunity to work directly alongside a highly active
CEO across multiple industries, rather than simply an administrative job.
Pay: $22.00 - $35.00 per hour
Benefits:
- 401(k)
- Dental insurance
- Flexible schedule
- Health insurance
- Life insurance
- Vision insurance
Education:
Experience:
- Administrative: 2 years (Preferred)
Ability to Commute:
- Naperville, IL 60563 (Preferred)
Willingness to travel:
Work Location: In person
