Women of Title Spotlight: Amy Gregory.
In the ever-evolving world of Title Insurance, there are exceptional leaders whose passion, dedication, and vision stand out. Today, we are excited to shine the spotlight on Amy Gregory, Chief Administrative Officer and President of Title Operations at Florida Agency Network (FAN). With nearly 30 years of experience in the title industry, Amy's journey is nothing short of inspiring.
A Small-Town Beginning with Big Dreams.
Amy hails from the small town of Lithia, Florida, nestled in the Tampa Bay area. Her career began humbly in high school when she landed a part-time role as a receptionist at Alday-Donalson Title through a business cooperative education program. "I remember walking into that office for my interview, nervous but excited. They were looking for a senior, but somehow, they saw potential in me. That job changed the trajectory of my life."
From receptionist to post-closing, processing, and eventually becoming a closer, Amy spent seven years honing her craft. She then transitioned to Fidelity National Title, where she excelled in closing and management roles. In 2007, Amy's path crossed with Aaron Davis, who was preparing to lead Hillsborough Title. "When Aaron and I sat down to discuss his vision for Hillsborough Title, I could feel his passion and drive. It felt like the perfect fit, and looking back, it was one of the best decisions I've ever made." Together, they built FAN into a network of over 50 title offices across Florida, supported by an ancillary company, accounting and IT services, and a team of over 200 professionals.
Leadership and Mentorship: Shaping the Next Generation.
Amy's passion for leadership and mentorship has been shaped by incredible women throughout her career. From Michelle Lawson and Tiffiney Daniels, who guided her early career, to Cathy Anderson and Carol Barry at Fidelity, Amy learned the value of investing in others. "These women didn’t just teach me about title insurance; they taught me about balance, resilience, and how to lead with grace."
Amy also highlights Gail Calhoun, founder of Hillsborough Title, and Debra Coffie from Alliant National Title, as pivotal mentors. "Gail showed me what it meant to lead with heart and persistence, and Debra demonstrated how faith and integrity can guide every decision you make."
When asked about challenges, Amy reflects on balancing her career with raising children.
"I was determined to excel in my career, but there were moments I missed important milestones with my kids. It’s one of my biggest lessons, and now I encourage my team to prioritize their families without guilt."
Advice for the Next Generation.
Amy encourages young women in the title industry to “follow your heart, learn from those who have paved the way, and embrace the power of mentorship.” She emphasizes, “Don’t be afraid to ask questions, and never underestimate the value of hard work and curiosity.”
Faith is a cornerstone of Amy’s journey, deeply influencing both her personal and professional life. As a leader, she strives to lead by example, allowing her faith to shine through her actions and dedicating herself to living a life that reflects God’s love.
Her "why" comes from her drive to push boundaries, continuous learning, and her love for a good challenge. "I thrive on seeing how far I can go—and then pushing just a little further. It keeps me motivated every day."
Books and Podcasts for Growth.
Amy is an avid reader and recommends titles like Start with Why by Simon Sinek, Daring Greatly by Brené Brown, and The Power of Moments by Chip & Dan Heath. "Each of these books taught me something profound about leadership, vulnerability, and creating meaningful experiences." Her go-to podcasts include "It’s a Good Life" by Brian Buffini, "The Ramsey Show" by Dave Ramsey, and "Elevate" by Robert Glazer.
Strength throughout the journey.
Amy finds her deepest source of strength in the memory of her late father, who instilled in her an unwavering commitment to integrity and the importance of a good reputation. “My dad always told me, ‘At the end of the day, your name and reputation are everything.’” Those words have become a guiding principle, shaping every decision she makes.
Equally steadfast is the support she receives from her husband of 27 years, Ryan. Theirs is a true fairy-tale romance—they met at just 13 years old and married at 19. Throughout their journey together, Ryan has remained her greatest champion, offering unwavering belief in her potential and constant encouragement as she pursued her career aspirations.
Trust, and Legacy.
Her guiding word is "Trust"—she strives to ensure everyone knows that if something is in her hands, it’s handled with care and precision. "Trust is everything. If people can trust me, then I’ve done my job well."
When asked about her legacy, Amy shares, "I want to be remembered as someone who led with kindness, consistency, and clarity. Someone who honored her journey, invested in others, and left a positive impact on those around her."
Outside of work, Amy has a surprising passion: singing. "Music has always been my escape and my joy. One day, I’m going to sing on a big stage—just wait!"
Final Thoughts for the Women of Title Community
Amy closes with gratitude, "Thank you for creating this incredible community. I’m excited to be part of it, to learn, and to share with so many inspiring women. Together, we’ll continue to make a difference."
Amy Gregory’s story is a testament to perseverance, passion, and the power of mentorship. She truly embodies the spirit of a Woman of Title—a leader who paves the way for others while staying true to her values.
Thank you, Amy, for being an inspiration to us all!
*Connect with Amy here: amy.gregory@flagency.net I LinkedIn I Facebook