Executive/Personal Assistant to Founder of Creative Community
Chicago, Cook County, Illinois, 60290, USA
Listed on 2026-01-12
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Administrative/Clerical
Office Administrator/ Coordinator, Virtual Assistant/ Remote Admin, Business Administration
Executive / Personal Assistant to Founder of Creative Community
Founder of an emerging creative community spanning music, hospitality, wellness, and nutrition seeks a highly capable Executive / Personal Assistant to support varied professional initiatives and day-to-day life operations. This is a unique, immersive role for someone who thrives in creative environments and enjoys being at the center of a growing, values-driven ecosystem. The principal is entrepreneurial, dynamic, and highly organized.
He needs someone who can foster an environment that promotes his ability to sustain his businesses and realize his vision. This is a person who themself is very disciplined and appreciates out-of-the-box thinking.
Compensation includes a monthly salary and a 1‑bedroom apartment in Lyndonville, VT. Periodic travel will be required as projects evolve, including to Bali. The position is in‑person while the principal is onsite, and there will likely be opportunities for some remote work.
Requirements- BA/BS from a competitive U.S. college or equivalent
- Minimum 2 years’ experience as a Personal Assistant, Executive Assistant, or similar role supporting a founder, creative, or entrepreneur
- Experience working in a professional or creative business environment
- Strong organizational and project management skills
- Excellent written and verbal communication
- High level of discretion, trustworthiness, and emotional intelligence
- Strong tech skills (Google Workspace, calendars, project tools, research)
- Ability to anticipate needs and manage competing priorities
- Interest or background in music, hospitality, wellness, nutrition, or creative communities (a plus)
- Comfort with travel and flexible scheduling
- Acting as primary right‑hand support to the founder across business and personal matters
- Managing calendar, scheduling appointments, and daily itinerary
- Planning travel (domestic and international)
- Coordinating with collaborators, artists, chefs, wellness practitioners, and partners
- Supporting creative projects, events, retreats, and community programming
- Overseeing household and day‑to‑day operations of the property
- Researching, sourcing, and managing vendors and service providers
- Attending meetings and summarizing key action items
- Creating systems, task lists, and workflows to support growth
- Anticipating needs and proactively solving problems before they arise
- Supporting on‑ground execution during travel or events (NYC, Bali, etc.)
Sunday‑Thursday 9 am‑5 pm
Salary: $5,000 /month + housing (1‑bedroom apartment in Lyndonville, VT)
Seniority levelNot Applicable
Employment typeFull‑time
Job functionAdministrative, Project Management, and Other
IndustriesStaffing and Recruiting
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