Executive Assistant

Hi, I’m Stu. I run an independent consulting practice that helps physicians, medical groups, and hospitals with the business side of healthcare. I've been doing this work for almost 20 years. With steady client work booked well into 2027, I’m looking for someone to help me keep track of commitments, make time for the highest priorities, and get things done while we continue to grow in a sustainable way.

You’ll work alongside me about 24 hours a week, in person, at a shared professional office in Arlington Heights, IL.

This is a right-hand role. Your main job will be to keep me organized and help me prioritize, so I can make the most of my work timeandmy personal time. I need someone who can look at the big picture, notice where support is needed, proactively draft a plan, and see it through.

• Continually tracking projects, tasks, and deadlines
• Monitoring my email inboxes and drafting replies
• Managing my professional and personal calendars
• Preparing for and following up after meetings (agendas, briefs, minutes, action items, thank-yous)
• Keeping my CRM database (in Notion) clean, tagged, and up to date
• Arranging travel for client visits and speaking engagements
• Handling invoicing and expense tracking
• Drafting outreach to my contact network (I'll teach you my system)
• Maintaining a content/newsletter calendar
• Coordinating with my wife Lauren, who provides marketing support for the business
• Other duties, as assigned

• Someone who thinks strategically and is also a bit obsessed with getting the details right
• A self-starter who is comfortable with ambiguity and asks the right questions to get the job done, so I don't have to manage them too closely, especially when instructions are incomplete or plans change
• Strong organizational and follow-through skills
• Good judgment about priorities and confidence taking initiative
• Sharp, discreet, and genuinely trustworthy with sensitive personal and business information
• A strong writer and communicator, as they'll be representing me in emails and phone calls
• Comfortable with everyday business software such as Notion, Microsoft 365 (Outlook, Word, PowerPoint, Teams, One Drive, and SharePoint), Google Workspace, Linked In, and Word Press
• Prior executive assistant, personal assistant, or office management experience is preferred
• Experience in healthcare or professional services is a plus, but not required

• $28–$36 per hour, depending on experience, as a W-2 employee
• About 24 hours a week to start, most likely over four days (we’ll work out the right schedule together)
• Paid time off
• Health insurance available through our group plan (employee-paid, subject to plan eligibility)
• I'll put real time into onboarding and giving you deep context for you how I work
• As trust builds, I expect your responsibilities to grow, and I'm open to hearing which areas interest you