Executive Assistant to CEO

We are looking for an Executive Assistant to work directly for the CEO. You will run the CEO's schedule, follow-ups and day-to-day logistics.

Reports to

CEO and Founder

Company

A multi-site healthcare operator (skilled nursing and post-acute care) based in Illinois

Location

Corporate office, in person. This is not a remote or hybrid role.

Type

Full-time

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. You will need to work out what is actually wanted and get it done without being walked through it.

Here is what that looks like in practice:

• Instructions come short. Expect a forwarded email that says only "add this to notes for the meeting with Aharon," "was this sent?" or "discussed with Jason why this needs to happen." Your job is to supply the context. Figure out which meeting it is, what should have been sent, and who still owes what.
• Priorities change mid-day. Meetings move, ideas show up spontaneously, and today's urgent item replaces yesterday's. Adjust quickly without needing the change explained.
• No surprises. Surface problems early. Keep the CEO copied on time-sensitive items, and report what is still open before anyone has to ask.
• Things said once still count. A passing mention is a commitment you are tracking.
• Ask good questions, not many of them. When something is unclear, ask one sharp question, or make a reasonable call and state the assumption. Do not stall, and do not guess silently.
• Slow things down when it matters. Sometimes the most valuable thing you can say is "Do you want to verify that before it goes out?" or "Here is what still needs confirmation."
• Bullet points and summaries. Updates should be short and decision-ready, not long narratives.

The right person reads this and thinks, "I can do that." The wrong person reads it and wants detailed instructions for every task.

Follow-through and loop-closing (the core of the job)

• 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. Use Fathom and AI tools to do it.
• Spot gaps and inconsistencies between notes, email and reports before they turn into problems.

Calendar and time

• 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, and make sure each one has a real calendar invite, an agenda and the right attendees.
• Arrange travel, conferences, hotels and event logistics.

Communication and preparation

• 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.

Recruiting and people projects

• Coordinate leadership hiring: candidate pipelines, interview sequencing, assessments and confidential candidate communication.
• Support HR and administrative projects such as evaluations, onboarding paperwork and records.

Confidential and personal support

• Handle sensitive business, financial, legal and personnel…