Join Our Team
We’re building an elite team of Family Assistants who use AI as their superpower. If you have the pedigree and the heart, we want to hear from you.
Family Assistant
As a Family Assistant at The Windermere Agency, you’ll serve as the operational chief-of-staff for up to four high-achieving families. You’ll be supported by Lumen — our proprietary AI system — and trained in the Path of the Luminary framework.
Who we’re looking for
- •3+ years in estate management, executive assistance, private household direction, or luxury concierge
- •Exceptional communication and discretion
- •Experience managing multiple stakeholders and complex logistics
- •Comfort with technology and AI-powered tools
- •Genuine care for families and their well-being
- •Based in or willing to relocate to the Orlando/Windermere area
Interested?
We hire selectively and train extensively. If this role resonates with you, send your resume and a brief note on why you’re drawn to this work to:
careers@thewindermereagency.com