Executive Assistant/Operations Manager (Greater Chicago Area)

Executive Assistant / Operations Manager

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

Reports To: Principals

Type: Full-Time

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