Executive Assistant to the CEO

Accolade Healthcare; Skokie (IL); On-site; USD 60,000 - 85,000; Full time

Job summary

Accolade Healthcare in Illinois seeks an Executive Assistant to the CEO to manage the CEO's schedule, follow-ups, and day-to-day logistics. The role is in-person at the corporate office, with a focus on intuition, proactive follow-through, and professional communication with executives, lenders, attorneys and partners.

Key tasks include turning meetings into actionable notes, maintaining a running item list, and coordinating recruiting and HR initiatives.

Qualifications

• Strong intuition and judgment; read between lines and act on incomplete direction.
• Relentless follow-through; track many open items and close without reminders.
• Excellent writing; draft clear emails in the CEO's voice.
• Confidence with senior executives, lenders, attorneys and outside partners.
• Advanced MS 365 skills (Outlook, Teams, Excel, Word).
• Discretion with confidential financial, legal and personnel matters.
• Able to work onsite at the corporate office full-time.

Responsibilities

• Follow-through and loop-closing: maintain a running list of items and drive each to completion.
• Follow up with employees, vendors, lenders, attorneys and outside contacts until finished.
• Turn meetings into clear notes: decisions, owners, deadlines and open items; use Fathom/AI tools.
• Spot gaps between notes, email and reports before issues arise.
• Calendar and time: manage the CEO's calendar with buffers and avoid back-to-back meetings.
• Communication and preparation: screen inbox, draft replies in the CEO's voice, prepare briefing notes.
• Recruiting and people projects: coordinate leadership hiring and HR/admin tasks.
• Confidential and personal support: handle sensitive information with discretion; assist with personal logistics.
• What success looks like: 30 days, 90 days, and 12 months milestones described for calendar, briefs and follow-through.

Skills

Intuition

Follow-through

Writing

Executive confidence

MS 365

Discretion

Onsite work

Tools

Fathom

AI tools

Job description

Position overview

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

Working with the CEO

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.

Key responsibilities

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 information with complete discretion.
• Help with personal logistics as needed, such as reminders, gifts, donations and vehicles.

What success looks like

30 days

Learned the CEO's calendar habits, key contacts and the leadership team. Built a running follow-up list the CEO trusts. Taken the inbox from reactive to organized.

90 days

Closed loops before the CEO has to ask about them. Briefing notes are ready ahead of every key meeting. People across the company know that a request routed through you gets done.

12 months

The CEO rarely repeats a request, is rarely surprised and spends time on deals and operations instead of chasing details.

Qualifications

Required

• Strong intuition and judgment. You can read between the lines, fill in missing context and act on incomplete direction.
• Relentless follow-through. You track many open items at once and close them without reminders.
• Excellent writing. You can draft clear, professional email in someone else's voice.
• Confidence with senior executives, lenders, attorneys and outside partners. You are comfortable politely pushing people for answers.
• Advanced Microsoft 365 skills (Outlook, Teams, Excel, Word). You 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.

Preferred

• Experience in healthcare, skilled nursing, real estate or another multi-site operating business.
• Experience coordinating recruiting and interviews.
• Comfortable working through Fathom, Claude, Copilot or similar AI tools.

This role is not a fit if you

• Need clear, complete instructions before you start a task.
• Wait to be reminded instead of reminding others.
• Get rattled when priorities change two or three times in a day.
• Hesitate to follow up a third time, or to tell a senior person something is wrong.
• Want a remote or hybrid schedule.