Chief of Staff / Executive Assistant A healthcare entrepreneur running several growing companies is looking for a right-hand person, someone who starts as a hands-on Executive Assistant and grows into a true Chief of Staff. Be honest with yourself before reading further: this is not a 9-to-5, and it does not start as a pure strategy seat. It starts hands-on. Early on you will manage calendars and email, keep projects moving, visit business sites, help capture content, and handle both business and personal errands. As you prove yourself, the role grows, more ownership, more strategy, more of my plate handed to you to simply handle. This is a build-up role for someone who wants to earn that trajectory, not skip to the end of it. You would work directly alongside the founder across multiple businesses in healthcare and hospitality. No two days look the same. What you would do
Manage email and calendar, and help move tasks to done, not just track them
Build and run a task management system so priorities stay clear and nothing slips
Keep the founder accountable and on track
Run vendor, admin, and operational projects start to finish
Handle business and personal errands as needed
Travel occasionally to business sites
Help capture short-form video content
As you grow, take things off the founder's plate and handle them without being asked
Over time, grow into the founder's network and the relationships across the businesses
Who this is for
You are resourceful. Handed something unfamiliar, you figure it out and get it done
You bring a problem and a proposed solution, not just the problem
You stay organized and calm when everything feels like a priority
You are comfortable with technology, AI tools like Claude or ChatGPT, and task or project management software
You are trustworthy with confidential information
You want a long-term working relationship and are willing to start hands-on to earn a bigger role
Logistics
Mostly in-person, especially early on, with occasional travel
Flexible hours, not a fixed schedule, not a weekend job
Based in the metro Detroit area
Benefits package included
Competitive salary, discussed based on fit and experience
If this sounds like the role you have been looking for, apply with a short note on why.