Chief of Staff (Westport)

Chief of Staff to a Top Luxury Real Estate Advisor

Westport, Connecticut (In-Person)

Full-Time | $80,000-$100,000 Depending on Experience + Performance Bonus

About the Opportunity

Cindy Raney & Team is one of Connecticuts top luxury real estate advisory practices - a high-performance, client-focused team redefining the real estate experience.

Were searching for a Chief of Staff to partner directly with Cindy Raney , one of the most accomplished real estate advisors in the country. This is not a traditional assistant role - its a chance to operate at the heart of a fast-moving, nationally recognized brand.

If youre smart, organized, tech-savvy, and driven by excellence, this is a front-row seat to learn how a top-producing real estate business runs - from leadership strategy to client experience execution.

What Youll Do

• Manage Cindys priorities, calendar, and meetings with precision.
• Attend client and internal meetings, take notes, and drive follow-through.
• Anticipate needs and solve problems proactively.
• Oversee communications and maintain key systems (Follow Up Boss, Outlook).
• Prepare materials for client appointments and strategic initiatives.
• Coordinate projects across marketing, operations, and client service.
• Explore technology and AI tools to improve efficiency and client experience.

Who You Are

Why This Role Is Exceptional

Bachelors degree required. Applicants must be authorized to work in the United States; sponsorship is not available.

To apply, send your rsum and a short note (250-300 words) on why this role excites you to Jason@cindyraney.com with the subject line : Chief of Staff Application - [Your Name]

About Cindy Raney & Team

Based in Westport, CT, Cindy Raney & Team represents Fairfield Countys most exceptional properties. We operate more like a private advisory firm than a brokerage - built on trust, intelligence, and shared success. Our motto : we win together, or not at all.