Executive Assistant

We are seeking a highly organized Executive Assistant / Operations Coordinator to provide administrative and operational support across several real estate-related businesses, primarily in residential sales, commercial sales, and property management, with some exposure to brokerage leadership, training, and coaching. This is a full-time, in-person role based primarily in Orland Park, with regular local travel throughout Will County, Southern Cook County, and occasionally Northwest Indiana. This is not a remote position. This is a strong opportunity for someone early in their administrative career who wants hands-on experience, variety, responsibility, and room to grow. The right person is reliable, detail-oriented, tech-comfortable, and able to manage multiple priorities without needing every task chased down. The ideal candidate has some administrative experience, strong written and verbal communication skills, and a high degree of follow-through. This person should enjoy using systems, checklists, calendars, CRMs, spreadsheets, email, and other technology tools to keep work organized and moving forward. Reliability, honesty, sound judgment, and consistent communication are critical in this role. Job Responsibilities Administrative & Executive Support Monitor, sort, prioritize, and respond to multiple Gmail inboxes and voicemails Assist with managing Google Calendars with multiple overlays Coordinate communication by phone, email, and text with agents, staff, contractors, tenants, attorneys, utility companies, vendors, virtual assistants, and other contacts Use Zoom to coordinate meetings, upload recordings, and manage meeting logistics Call attendees to confirm meetings and events Coordinate the purchase of office supplies and consumables CRM, Marketing & Communication Help manage a CRM database of 6,000+ contacts Enter and update contact records Create and apply action plans Monitor activity, create call lists, log notes, and assist with follow-up communication Assist with obtaining client reviews, testimonials, and referrals Assist with managing internet presence, including Facebook and Instagram business pages, Google Business Profile, Google Local Services ads, and website updates Assist with recording, organizing, and uploading video content Help plan and coordinate occasional events for 30 to 150 people Fill out agreements, contracts, forms, and other documents using Microsoft Word, Google Docs, PDF editing software, and e-signature platforms Coordinate all aspects of purchase & sale transactions through closing Pick up and drop off keys, lockboxes, checks, contracts, and other items from offices and properties Visit owned properties to visually inspect, take photos, grant access to contractors, meet city inspectors, coordinate utility access, and assist with other property-related tasks Research, contact, and vet third-party service providers, vendors, contractors, and product providers Tracking & Reporting Record production results, rents, and other tracking data Help prepare reports and summaries Maintain systems, checklists, and recurring workflows What Success Looks Like Success in this role means fewer dropped balls, faster follow-through, cleaner systems, better communication, and more time freed up for business growth. The right person will help keep priorities organized, communication moving, and important details from slipping through the cracks. Excellent written and verbal communication skills Strong organizational ability High attention to detail Comfortable managing many ongoing priorities Preference for using systems and checklists Able to adapt to changing schedules and business needs Comfortable learning new technology systems Positive, professional attitude Reliable, honest, and accountable Qualifications & Experience 2-4 years of administrative, executive assistant, office support, or similar experience preferred Proficient in Google Workspace, including Drive, Gmail, Calendar, Docs, Sheets, and Google Voice Proficient in Microsoft Office, especially Word and Excel Familiarity with common business tools such as Zoom, DocuSign, CRM systems, PDF editing tools, and similar platforms Experience using or operating a CRM preferred Valid driver’s license and reliable transportation required High school diploma or equivalent required Real estate, property management, or leadership experience is a plus Location Primary office location: Orland Park, IL Additional local travel may include Oak Lawn, Will County, Southern Cook County, offices, owned properties, vendor locations, and other business-related stops. This is an in-person role with local travel. Reliable transportation is required. Schedule Full-time Monday through Friday 8:30 AM to 5:00 PM Expected hours: 40 per week Compensation $16-$18 per hour, based on experience Additional opportunities may include: Performance-based incentives Growth opportunities across multiple real estate-related businesses Access to industry-leading training and personal growth opportunities #J-18808-Ljbffr Chicago Southland Homes