Executive Assistant (for CEO of Skilled Nursing Facilities)

We are a multi-site healthcare operator delivering skilled nursing, rehabilitation, and post-acute care across multiple communities in Illinois. Supported by a central corporate office, our organization focuses on operational excellence, quality resident care, and strategic growth. We move fast, value direct execution, and rely on a high-accountability corporate team to support our facilities, leadership, and external partners.

We are looking for an Executive Assistant to work directly for the CEO and Founder in a full-time, in-person role at our corporate office (this is not a remote or hybrid role). You will run the CEO's schedule, follow-ups, and day-to-day logistics. The most important skill for this job is intuition: the CEO moves fast, thinks out loud, and often hands off work in a one-line email or a quick comment between meetings, requiring you to work out what is actually wanted and get it done without being walked through it. Instructions will come short, priorities change mid-day, and you must adjust quickly, surface problems early so there are no surprises, track passing mentions as commitments, and ask sharp questions rather than stalling or guessing silently. Updates must be kept short, clear, and decision-ready. The right person reads this and thinks "I can do that," while the wrong person reads it and wants detailed instructions for every task.

Responsibilities

• Keep one running list of everything the CEO has asked for, committed to, or handed to someone else, and drive each item to done.
• Follow up with employees, vendors, lenders, attorneys, and outside contacts until things are finished; be persistent and polite, and call when an email gets no answer.
• Turn meetings, including the weekly leadership meeting, into clear notes: decisions, owners, deadlines, and open items to carry into the next meeting using Fathom and AI tools.
• Spot gaps and inconsistencies between notes, email, and reports before they turn into problems.
• Manage the CEO's calendar directly; protect buffers of about 30 minutes, avoid stacking meetings back to back, and keep Friday afternoons light when possible.
• Schedule internal meetings, facility visits, interviews, and outside calls, making sure each one has a real calendar invite, an agenda, and the right attendees.
• Arrange travel, conferences, hotels, and event logistics.
• Screen the CEO's inbox; flag what needs the CEO, handle what doesn't, and draft replies in the CEO's voice.
• Prepare short briefing notes and materials before meetings, including current data, open issues, and talking points.
• Act as a professional point of contact for the leadership team, facility administrators, candidates, vendors, and outside partners.
• Coordinate leadership hiring: candidate pipelines, interview sequencing, assessments, and confidential candidate communication.
• Support HR and administrative projects such as evaluations, onboarding paperwork, and records.
• Handle sensitive business, financial, legal, and personnel information with complete discretion.
• Help with personal logistics as needed, such as reminders, gifts, donations, and vehicles.

Qualifications

• Strong intuition and judgment with the ability to read between the lines, fill in missing context, and act on incomplete direction.
• Relentless follow-through to track many open items at once and close them without reminders.
• Excellent writing skills to draft clear, professional email in someone else's voice.
• Confidence with senior executives, lenders, attorneys, and outside partners, comfortable politely pushing people for answers.
• Advanced Microsoft 365 skills (Outlook, Teams, Excel, Word) and ability to pick up new tools quickly, including AI note-takers and assistants.
• Complete discretion with confidential financial, legal, and personnel matters.
• Able to work onsite at the corporate office full-time (not a fit for remote or hybrid schedules).
• Experience in healthcare, skilled nursing, real estate, or another multi-site operating business preferred.
• Experience coordinating recruiting and interviews preferred.
• Experience with Fathom, Claude, Copilot, or similar AI tools preferred.
• Not a fit if you need clear, complete instructions before starting a task, wait to be reminded, get rattled by mid-day priority changes, or hesitate to follow up multiple times.

Compensation

• $60,000 – $75,000 per year
• Full-time, in-person role at the corporate office