Executive Assistant & Operations Manager

Part-Time | 20 Hours/Week | Remote-Friendly | Chicago Preferred, but not required I'm Michelle — a People & Organizational Strategy executive, consultant, real estate investor, educator, and yoga teacher building what I call a portfolio life. My work sits at the intersection of people strategy, real estate, wellness, teaching, and community-building. On any given week, I might be advising a leadership team, facilitating a workshop, coordinating a property project, teaching a class, speaking at an event, or hosting a gathering on Chicago's South Side. Rather than building a traditional career around one role or one company, I've intentionally built multiple streams of work and impact. It's rewarding, meaningful, and increasingly complex. That's where you come in. About The Role I'm looking for an Executive Assistant & Operations Manager who can serve as the operational anchor across my portfolio. Your job is to create reliability. Maintain momentum. Make sure important things don't fall through the cracks. This role is primarily focused on three areas: 1. Calendar & Time Management 2. Inbox & Communications 3. Real Estate Coordination You will help manage competing priorities across consulting clients, teaching commitments, speaking engagements, real estate projects, and personal commitments. This is not a traditional assistant role where you simply wait for instructions. I'm looking for someone who notices patterns, proactively follows up, protects priorities, and helps create the operational stability that allows me to focus on strategy, relationships, and growth. --- What You'll Own 1. Calendar & Time Management (Priority 1) -Fully manage scheduling across approximately five calendars -Build weekly flows aligned with energy, capacity, and deadlines -Protect deep work blocks, restoration time, and key priorities -Coordinate across multiple platforms and stakeholders -Anticipate conflicts and trade-offs before they become problems -Plan ahead for conferences, speaking engagements, travel, and seasonal priorities 2. Inbox & Communications Flow (Priority 1) -Triage email and text threads -Draft clear, warm, concise communication in my voice -Maintain follow-up systems so nothing slips -Coordinate communication with clients, collaborators, vendors, and property managers -Escalate time-sensitive issues appropriately -Keep communication organized and actionable 3. Real Estate Coordination (Priority 2) -Track property timelines, permits, violations, and vendor updates across three Chicago properties -Follow up consistently with contractors and property managers -Maintain a simple dashboard of tasks, deadlines, and decisions needed -Organize receipts, invoices, and documentation for bookkeeping -Monitor compliance deadlines and outstanding action items This is frequent but relatively lightweight work. Success comes from consistency, follow-through, and attention to detail rather than deep real estate expertise.* --- What Makes Someone Exceptional In This Role The strongest candidates will: -Love creating order from complexity -Naturally follow up without being asked -Have excellent written communication skills -Enjoy managing details others overlook -Be comfortable making judgment calls within clear parameters -Know how to prioritize when everything feels important -Stay calm when plans change -Balance warmth with accountability -Take pride in being dependable You don't need to be a Chief of Staff or strategic advisor. You don't need to be a Chief of Staff or strategic advisor. Your primary value is operational reliability, excellent judgment, and consistent follow-through. --- Why This Role Is Different -You'll support a founder managing multiple businesses, properties, and commitments -You'll have meaningful ownership rather than simply taking direction -You'll work directly with the decision-maker -You'll help create capacity for work that impacts organizations, communities, and people -As trust develops, there may be opportunities to expand the role based on your strengths and interests --- What This Role Is NOT This role is not focused on: -Strategic consulting -Social media management -Content creation -Personal errands -Bookkeeping or accounting -HR consulting -Full-scale project management Those areas may evolve over time, but the immediate need is operational reliability. --- What Success Looks Like 30 Days * You understand the architecture of my portfolio * Calendar management is running smoothly * Inbox triage systems are established * You understand key stakeholders and recurring priorities 90 Days * You're proactively managing trade-offs and conflicts * Most communications require minimal editing * You're catching issues before they become problems * You understand my capacity, preferences, and priorities 6 Months * You operate core infrastructure with confidence * You anticipate needs before they're expressed * Real estate coordination runs smoothly * I trust your judgment * My weeks feel more spacious, intentional, and focused --- Working Style * Flexibility is important, but reliability is non-negotiable * Clear communication matters more than constant availability * I value ownership, curiosity, kindness, and follow-through --- How To Apply Please send: 1. A brief cover letter sharing: -Why this role appeals to you -Your availability to commit 20 hours per week -Your availability for a first-round interview 2. Your resume 3. A real example of how you've managed a complex calendar and inbox Please include: -The tools you used -How you prioritized competing demands -How you tracked follow-ups -Any systems, workflows, or templates you created Bonus Question: Tell me about a time when you prevented a problem before your executive knew it existed. I'm looking for someone who enjoys creating order, solving problems, and helping ambitious work happen. If that's you, I'd love to hear from you.