Executive Assistant​/Operations Manager

Location: Chicago (River North), onsite Monday–Friday

Reports To: Principals

Type: Full-Time

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.

• 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

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

• 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 Word Press;
  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