Stephanie Woolsey
Stephanie Woolsey is a dynamic learning and development leader currently serving as Training Manager at W.W. Gay Mechanical Contractor, Inc. in Jacksonville, Florida. In her role, she is responsible for building and leading the organization’s training function from the ground up—designing programs that strengthen workforce capability, support business growth, and foster a culture of continuous learning. Known for her strategic mindset and people-first approach, Stephanie is passionate about equipping employees with the knowledge, confidence, and tools they need to succeed in an evolving workplace.
Stephanie’s career path reflects a strong foundation in both education and talent development. She began her professional journey as a middle school educator, where she spent over eight years developing curriculum, leading classrooms, and mentoring students and colleagues. Transitioning into the corporate space, she worked as a recruiter, sharpening her skills in talent acquisition, relationship building, and organizational strategy. These combined experiences uniquely position her to bridge learning, performance, and workforce development in meaningful ways.
She holds a Master of Education from the University of Montevallo and a Bachelor of Science in Marketing from Auburn University. An active member of the Association for Talent Development (ATD), Stephanie also contributes to the professional community as Director of Programs for ATD NEFL. She has earned a Leading Leadership Development Certificate and continues to advocate for innovative learning strategies, including the integration of AI and capability building in the workplace. Stephanie is recognized for her adaptability, creativity, and dedication to helping both individuals and organizations reach their full potential.
• Member of the Association for Talent Development (ATD)
• Leading Leadership Development Certificate
• University of Montevallo
• Auburn University
• Nominated for Teacher of the Year
• Association of Talent Development (ATD)
• ATD NEFL
What do you attribute your success to?
I had such an excellent example growing up. We kind of had an opposite family - my dad retired early and stayed home with us, while my mom worked and was CFO of a company for 30 plus years. She's still working now just because she likes to work. Watching her be successful and be such a powerhouse of a woman was inspiring. I've always had this drive of wanting to work with people. I've always known I like to work. And then adding on the education piece, I realized I like to help. I like to share knowledge and make people feel empowered and confident in what they're doing, and I think that's what keeps me going each day.
What advice would you give to young women entering your industry?
I would say listen to your gut and don't be scared of saying no, and also saying yes. Before I considered interviewing for the job I'm in now, I had just been passed over for a promotion at the place I was working before in recruiting. I was so upset at the time, but it was my best no. It pushed me into the best yes. It all happened within a week of each other. I had a hard time finding a teaching job when I graduated in 2007, and by the time I was out of grad school in 2011, it was hard to find a teaching job in Alabama, and then I ended up in Florida. So just don't be scared of the nos, because it'll happen.
What values are most important to you in your work and personal life?
The values most important to me in both my work and personal life are growth, balance, and meaningful connection. I have a strong love for learning and enjoy spending my free time reading and exploring new ideas, which continually fuels both my personal and professional development. I also prioritize staying active—whether it’s going for a run with friends or spending time outdoors, especially at the beach, appreciating the beauty of Florida.
At this stage in my life, I truly value having the time and energy to be present and enjoy new experiences. With my new position, I’ve been able to embrace a healthier balance, allowing me to explore new interests, take on new adventures, and look ahead with excitement for what’s next.