Job Description

Chief of Staff to a Top Luxury Real Estate Advisor

Westport, Connecticut (In-Person)

Full-Time | $65,000-$75,000 Depending on Experience + Performance Bonus

About the Opportunity

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

We’re 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 - it’s a chance to operate at the heart of a fast-moving, nationally recognized brand.

If you’re 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 You’ll Do

• Manage Cindy’s 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

• High-energy, curious, and resourceful.
• Organized and detail oriented.
• Tech-confident. You love discovering better ways to work.
• Collaborative. You understand that great teams outperform great individuals.
• Professional and polished. You’re comfortable engaging with high-net-worth clients.
• Motivated by growth. You want to build something meaningful and learn from the best.

Why This Role Is Exceptional

• Direct mentorship from one of the country’s top real estate advisors.
• Learn how a luxury real estate business operates at scale.
• Work inside a collaborative, values-driven culture.
• Competitive compensation with performance-based bonuses.
• The experience and exposure to fast-track your career in real estate, business, or leadership.

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

To apply, send your résumé 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 County’s 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.

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