🌟 About the Role
This is not a standard Executive Assistant role.
You will work closely — every day, in constant communication — with the CEO of a U.S.-based group of 10 companies across healthcare, technology, telecommunications, retail, and education. Over 180 full-time employees depend on his work. As his Executive & Personal Assistant, you will be inside that work, on both business and personal matters.
This is one of the closest working relationships in any of the 10 companies. The role is built on trust, discretion, and proximity. You will be the person in their corner.
📋 Position Overview
• Position: Executive & Personal Assistant (Remote)
• Work Type: Full-Time · Long-Term · Single Working Commitment
• Working Hours: Aligned with U.S. Business Hours (CST, Chicago)
• Location: Remote / Work From Home,
• Experience: The right person over the right resume
💼 What You'll Be Doing — On the Business Side
• Stay in constant, two-way communication with the CEO throughout the day
• Manage schedules, meetings, appointments, and reminders
• Handle communication and correspondence professionally on behalf of leadership
• Prepare reports, presentations, spreadsheets, and documents as needed
• Coordinate across the company's 10 businesses and assist with project management
• Conduct research and compile information to support business operations
• Track tasks, follow-ups, and deadlines through to completion
🤝 What You'll Be Doing — On the Personal Side
• Manage both business and personal calendars as a single, unified view
• Handle personal correspondence, appointments, reservations, and errands
• Coordinate personal travel, accommodations, and itineraries
• Liaise with vendors, deliveries, and household-related logistics
• Handle confidential personal matters with discretion and care
• Be the single point of contact for everything that touches the CEO's day
✨ Skills & Setup — What We're Looking For
• Strong English communication skills, written and verbal
• Excellent organisational and time-management abilities
• Comfortable working independently in a remote environment
• Basic proficiency with Google Workspace or Microsoft Office tools
• Stable internet, professional workspace, camera availability for meetings
• Interest in AI, software, digital marketing, or automation is a plus
The CEO works at the cutting edge of AI and entrepreneurship and has built and sold multiple companies. The work is fast-moving and often without precedent — which means the spirit you bring matters more than the skills you arrive with. We are looking, above all, for excitement to work closely with him and a genuine willingness to learn. Skills can be taught; enthusiasm cannot.
⚜️ What This Role Asks of You
• Constant communication. You proactively reach out — not only when asked
• Closeness. You will know things most people in the 10 companies never will
• Discretion. What happens between you stays between you
• Reliability. When the CEO calls, you respond
• Full commitment. This must be your only employment — no second job, no freelance work, no parallel projects
• Enjoyment of the work. The closeness is the point, not a side-effect
Tensor Solutions · Chicago
