Her Story
About Holly
Holly Bailey is a seasoned operations executive and community management leader with more than 20 years of experience in real estate management, resort operations, community associations, construction, and organizational leadership. Throughout her career, she has developed a comprehensive understanding of the real estate industry, building expertise across property management, construction renovations, financial oversight, capital planning, and operational strategy. As a licensed Florida Community Association Manager (LCAM) and Certified Manager of Community Associations (CMCA), Holly is recognized for her ability to transform complex organizations, improve performance, and create sustainable systems that drive long-term growth and value.
Holly began her career at a young age in property management before launching her own construction renovation company, where she gained hands-on experience managing projects, budgets, and business operations. Her transition into resort management in Florida shortly before the COVID-19 pandemic introduced her to the community association industry and led her to earn her CAM license. Over the past decade, she has concentrated on the operational side of real estate management, believing that while every organization offers a different product or service, successful businesses are ultimately built on strong operational foundations. Her experience includes construction management in Las Vegas, operational consulting, portfolio management, and leadership roles overseeing homeowner associations, commercial properties, development districts, and resort communities. During the challenges of the pandemic, she successfully developed innovative strategies that enabled resort operations to remain resilient and financially viable, further strengthening her expertise in budgeting, financial management, structural and capital planning, regulatory compliance, and stakeholder engagement.
Currently serving as Executive Director of Treasure Island Resort in Florida’s Panhandle, Holly oversees a 263-unit resort operation consisting of both a condominium association and a rental management entity. In this role, she leads all aspects of budgeting, financial management, staffing, leadership development, training, capital improvement projects, and public relations. Since assuming the position, she has focused on evaluating and restructuring operational processes, implementing new staff leadership and promotion programs, and strengthening organizational alignment to support future growth. Known for her strategic mindset, collaborative leadership style, and results-driven approach, Holly excels at bringing together financial performance, operational efficiency, and community engagement to create thriving organizations and exceptional stakeholder experiences.
Her Interview
Ten minutes with Holly
01What do you attribute your success to?
I attribute my success to integrity and doing everything with good intention. I always tell people, if you do everything with good intention, and it's the next right thing, it doesn't matter the outcome - you've already succeeded. That's something I train my staff and my kids. Everything will fall underneath that - your honesty will come from it, your work ethic will come from it. I also believe in being good and happy at the position you're in. Not everybody wants to be a manager - some people just like to come and do their job and be happy with it, and other people want to grow. I really take the time wherever I'm at to watch my team members. If I give a task, do they do it? How are they talking to their team members? I ask them: did everything you do today - could you look in the mirror and say, I was the best I could be today? Those two things are key: just do the next right thing, and do it with good intention and integrity.
02What are the biggest challenges or opportunities in your field right now?
One of the biggest challenges I'm seeing in this industry is that there's no advocacy. It's unfortunate - CAMs get burned out very quickly. Our job is to find what's wrong every day and tell somebody it needs to be fixed. When you get these large corporations and management companies, it's easy for them to recognize the people within their immediate company, but when you're a remote or an off-site manager, it becomes a little bit more stressful. Board members are frustrated. That's part of why I'm going back to school for a pre-law degree - I want to see where it could go in terms of creating more mentorship and advocacy for this field. That culture of work environments is so hard, especially in association management, and advocacy and mentorship are really important to me. On the opportunity side, we're at a point in time where technology has advanced, softwares have advanced, and now you really need to have additional skills in order to excel. You want to be cross-trained, to have that versatility to be able to do different jobs under one umbrella. For resorts specifically, after the world exploded with Airbnbs as the safer thing to do during COVID, it calmed down again, and now resorts have to look at how to be competitive. In my opinion, it's not necessarily what your condo offers, but it's the atmosphere and the culture that your condo offers that sets you apart, because there's just so many options to choose from.
03What values are most important to you in your work and personal life?
Integrity is the most important value to me. I always tell people, if you do everything with good intention, and it's the next right thing, it doesn't matter the outcome you've already succeeded. That's something that I train my staff and my kids. Everything will fall underneath that your honesty will come from it, your work ethic will come from it. I also value being good and happy at the position you're in. Not everybody wants to be a manager some people just like to come and do their job and be happy with it, and other people want to grow. I really take that time wherever I'm at to watch my team members and help them develop. I ask: did you do everything today where you could look in the mirror and say, I was the best I could be today? Those are the two key things: just do the next right thing, and do it with good intention and integrity. I also value mentorship and advocacy, and that culture of work environments. Watching those that work with me and those that have worked for me grow - I love that. That's a really big thing to me.
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