Executive Assistant/Operations Manager

About the Role

We’re looking for a highly organized, proactive Executive Assistant / Operations Manager to serve as the quarterback of our business operations. This role goes well beyond calendar management. You’ll be the right hand to the Principals: anticipating needs, coordinating key initiatives, and driving execution across the organization.

This role suits someone who thrives in a fast-paced environment, takes charge without constant direction, and wants a central role in scaling a growing real estate business.

Key Responsibilities

Executive Support

• Serve as the primary point of contact between the Principals and internal and external stakeholders
• Manage the Principals’ calendars and prioritize meetings
• Prepare agendas, take concise notes, and drive follow-through on action items
• Keep the Principals briefed with the right context, data, and updates to make quick decisions
• Own internal projects, keeping deadlines on track and stakeholders aligned
• Identify workflow gaps and recommend improvements

Communications & Brand

• Draft correspondence, presentations, and reports
• Maintain the company website, including content updates and listings
• Manage the company’s LinkedIn presence with a consistent brand voice

Real Estate Operations

• Track deal flow and key timelines for acquisitions, leases, and dispositions
• Support due diligence by gathering and organizing property documents, contracts, and vendor materials
• Coordinate across acquisitions, asset management, the Principals, and third parties
• Schedule property tours, inspections, and meetings
• Maintain internal databases, project files, and document storage

Administrative & Financial

• Open property bank accounts for new acquisitions and refinances
• Prepare service contracts and engage vendors
• Respond to tenant requests
• Deposit rent checks and reconcile credit card statements
• Handle travel planning and day-to-day office management
• Coordinate with third party IT provider

Qualifications

• 3+ years in executive support, chief of staff, or operations
• Self-starter with a strong sense of ownership and accountability
• Exceptional organization, communication, and problem-solving skills
• Able to manage multiple priorities calmly
• Discretion and professionalism with confidential information
• Proficient in Microsoft Office (Outlook, Teams, Excel, PowerPoint, Word), Adobe, and WordPress; Rent Manager or similar property management software a plus
• Experience with LLC formation and related filings
• Illinois notary, or willing to become one within 120 days of start

Pay: Up to $105,000.00 per year

Benefits:

• 401(k) matching
• Dental insurance
• Health insurance
• Vision insurance

Application Question(s):

• Willing to be onsite, greater Chicago area, 5 days a week

Experience:

• Executive administrative support: 3 years (Required)

Location:

• Chicago, IL 60654 (Preferred)

Work Location: In person