Executive Assistant to President / Business Operations Coordinator

Location: Chicago and surrounding suburbs (currently Buffalo Grove)
Employment Type: Full-Time
Schedule: Monday–Friday, with occasional evenings or weekends as business needs require
Reports To: President / Owner
Compensation: Competitive, based on experience

About the Position

We are seeking a highly organized, resourceful, and proactive Executive Assistant to work directly with the President and Owner of a diverse portfolio of businesses in the Chicago area.

Our businesses span the restaurant, bakery, retail, hospitality, entertainment, and consulting industries.

This is a unique opportunity to work closely with an entrepreneur overseeing multiple growing companies, including Hello Kitty Café Chicago, Hello Tokyo, Good Fortune Baking, and other hospitality and retail ventures.

The ideal candidate is someone who thrives in a fast-paced entrepreneurial environment, takes initiative, solves problems independently, and can manage multiple priorities simultaneously.

This is not a traditional administrative assistant position. We are looking for a trusted right-hand person who can help coordinate day-to-day business activities, oversee follow-ups, manage special projects, and ensure that important responsibilities are completed efficiently.

Key ResponsibilitiesExecutive & Personal Assistance

• Manage the President's calendar, appointments, meetings, and daily schedule.
• Organize and prioritize emails, correspondence, and communications.
• Coordinate business and personal travel arrangements.
• Prepare documents, presentations, spreadsheets, reports, and correspondence.
• Maintain confidential business and personal records.
• Assist with personal appointments, errands, and logistical arrangements as needed.

Business Operations Coordination

• Serve as a central point of communication between the President, managers, employees, vendors, and business partners.
• Follow up with management teams regarding assigned tasks, deadlines, and operational issues.
• Track outstanding projects and ensure timely completion.
• Help identify operational problems and coordinate solutions.
• Assist with employee onboarding, scheduling coordination, and administrative HR matters.
• Coordinate with payroll providers, accountants, attorneys, and outside consultants.
• Visit business locations as necessary to check on projects and report progress.

Vendor & Project Management

• Communicate with suppliers, contractors, landlords, and service providers.
• Request quotes, compare pricing, and coordinate purchasing.
• Track vendor orders, deliveries, invoices, and outstanding issues.
• Coordinate maintenance, repairs, installations, and renovations.
• Manage project timelines and provide regular progress updates.
• Research products, services, and business opportunities.

Financial & Administrative Support

• Organize invoices, receipts, contracts, and financial documents.
• Monitor upcoming payments, renewals, and administrative deadlines.
• Assist with expense tracking, invoice verification, and basic reporting.
• Prepare business performance summaries using information from managers and existing systems.
• Coordinate with bookkeeping and accounting teams.
• Maintain organized digital files and records across multiple companies.

Marketing & Special Projects

• Assist with coordinating marketing initiatives, promotions, and special events.
• Communicate with marketing agencies, designers, and outside partners.
• Help organize private events, business meetings, and promotional activities.
• Research new business concepts, potential vendors, and expansion opportunities.
• Support new business openings and other special projects assigned by the President.

Qualifications

• Minimum 3 years of experience in executive assistance, business administration, operations coordination, or a similar role.
• Experience supporting a business owner, entrepreneur, or senior executive strongly preferred.
• Exceptional organizational skills and attention to detail.
• Strong written and verbal communication skills.
• Ability to manage multiple companies, projects, and competing deadlines.
• Excellent problem-solving skills and independent judgment.
• Proficiency in Microsoft Office, Google Workspace, spreadsheets, and modern business software.
• Comfortable learning new technology, including AI productivity tools.
• High level of discretion, professionalism, and confidentiality.
• Valid driver's license and ability to travel between Chicago-area business locations.
• Hospitality, restaurant, or retail experience is a plus, but not required.

Ideal Candidate

We are looking for someone who:

• Takes ownership: Doesn't wait to be told every step and follows tasks through to completion.
• Is exceptionally organized: Keeps track of deadlines, responsibilities, and details across multiple businesses.
• Is resourceful: Can research problems, identify solutions, and present recommendations.
• Communicates effectively: Provides concise updates and knows when an issue requires the President's attention.
• Is adaptable: Comfortable switching between executive support, business operations, and personal assistance.
• Is trustworthy: Handles confidential business, financial, and personal matters with discretion.
• Gets things done: Focuses on execution, accountability, and results.

What Success Looks Like

Within the first 90 days, the successful candidate will have established an organized system for managing the President's schedule, communications, business priorities, and outstanding projects.

The candidate will independently coordinate routine administrative matters, follow up with management teams, and provide clear daily updates on priorities and unresolved issues.

Our goal is to find someone who can grow with the organization and become a long-term, trusted member of the executive team.

To Apply: Please submit your résumé and a brief description of your experience supporting executives, business owners, or multiple business operations.

Pay: $63,900.00 - $77,000.00 per year

Benefits:

• Flexible schedule

Work Location: In person