Executive Assistant / Chief of Staff

Job Description: We're hiring an Executive Assistant / Chief of Staff to support the CEO of a growing portfolio of companies in healthcare, wellness, and hospitality, based in Oakland County, Michigan. This is a true right\-hand role. You'll work directly alongside the CEO, manage the moving parts across multiple businesses, and grow over time into a full Chief of Staff. The role starts hands\-on and expands as trust is built. What you'll do: Keep the CEO accountable and on track — redirect when needed, own the follow\-through Manage calendar, email, and inbox triage Build and run a task management system that keeps priorities clear Run vendor, admin, and operational projects start to finish across multiple businesses Travel throughout the month to various business sites across Michigan Handle the occasional business or personal errand Take items off the CEO's plate and handle them independently Grow into network and relationship management across the businesses What we're looking for: 2\+ years of executive assistant experience (required) A thinking partner — someone who builds with us, not just executes tasks Confident enough to push back, ask hard questions, and own the outcome of the CEO's time Resourceful with unfamiliar problems Brings a problem and a proposed solution Stays organized and calm when everything feels like a priority Experienced with technology and AI tools (Claude, ChatGPT, task management software) Trustworthy with confidential information Wants a long\-term role with a real growth path Logistics: Fully on\-site in Oakland County, Michigan Regular travel to business sites across Michigan Consistent weekly schedule Benefits package included To apply: Submit your resume and a short note about why this role interests you. As part of your application, email Cyrus@GoRonin.com with the subject line "ATTN Indeed Applicant" and share a brief story about a time you figured out something unfamiliar. Pay: $48,988\.03 \- $75,000\.00 per year Benefits: Health insurance Paid time off Vision insurance Application Question(s): How many years of Executive Assistant experience do you have? Are you comfortable handling both business and occasional personal errands as part of this role? Are you available to work fully on\-site in Oakland County, Michigan, with no remote option? Do you have experience supporting a founder, owner, or principal directly — not just supporting a team or department? Are you willing to email a short story (about a time you figured out something unfamiliar) to Cyrus@GoRonin.com with the subject line "ATTN Indeed Applicant"? Are you experienced with AI tools like Claude or ChatGPT in a work setting? Do you have experience in healthcare, wellness, or hospitality operations? Are you comfortable working in a fast\-paced environment where priorities shift, multiple projects run in parallel, and no two days look the same? Are you comfortable working in a direct, fast\-feedback environment where you may be asked to push back on the CEO and own decisions about how their time is spent? Are you comfortable being given a goal with minimal instructions and figuring out how to execute it independently? Please include your LinkedIn link in your email or resume. Ability to Commute: Bloomfield Hills, MI 48301 (Required) Willingness to travel: * 25% (Required) Work Location: In person