Cyndee Haydon

Cyndee Haydon has stayed ahead of the curve throughout her career. With a Computer Science Business degree, early years at IBM, and two decades building a referral-driven real estate business along the Pinellas Gulf Beaches, she has always known how to make technology work for people, not the other way around.

She pioneered video testimonials in 2006, and today she leads the conversation on practical AI adoption in real estate, helping agents automate the routine so they can focus on the relationships that build a business.

Her real estate specialty is short-term rental investment on the Pinellas Gulf Beaches. With 435+ transactions and $230M+ in sales, including 150+ vacation rental transactions, Cyndee helps buyers and sellers answer one question: which properties actually perform as short-term rentals, and which do not? She uses her Haydon SHORE™ STR Investment Framework to evaluate supply and demand, rental rules, operating economics, risk and resilience, and guest experience. She routinely advises against more properties than she recommends, and that honesty is the foundation of the trust her clients, and increasingly AI search tools, place in her.

As founder of the AI That’s Easy™ Implementers Club Skool and the Still Human, Just Smarter movement, Cyndee teaches real estate professionals to use AI and AI visibility strategy with confidence, clarity, and a relationship-first mindset. Her approach is honest, immediately actionable, and anything but overwhelming.

A nationally recognized speaker, insurance expert, and author of seven books for sellers, Cyndee serves as the 2026 Florida Realtors® Treasurer and 2026 NAR Regulatory Issues Forum Chair. She is a Broker Associate with the Sandbars to Sunsets Team at Future Home Realty.