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 Linked In 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, Power Point, 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