Her Story
About Ashley
Ashley Thomas is a financial services and compliance executive with more than 17 years of experience spanning banking, operations, leadership, regulatory oversight, and investment adviser compliance. Inspired by her mother’s strong work ethic and encouraged by her natural love of math and problem-solving, Ashley pursued dual degrees in Accounting and Finance from the University of South Florida. She began her career in 2009 as a teller at Wachovia, which was later acquired by Wells Fargo, and steadily advanced through a series of leadership and client-facing roles. Her dedication and expertise ultimately led her to become a licensed private banker, managing relationships with affluent clients and helping them achieve their financial goals. Throughout her career, she has been guided and inspired by respected mentor Lilly Machin, whose leadership and support helped shape Ashley’s professional development and commitment to excellence.
In 2018, Ashley joined Raymond James Financial, where she spent several years building and leading teams within back-office operations, foreign and entity account management, and regulatory reporting. Managing teams of 10 to 25 professionals across multiple U.S. locations, she developed extensive expertise in operational controls, risk management, and regulatory processes. Following a pivotal career transition, Ashley moved into compliance-focused roles, serving as a Senior Advisor for Compliance Assurance and Internal Controls before becoming a Compliance Manager within the firm's RIA division. There, she conducted annual ADV reviews, registration reviews, surveillance and trend reporting, and compliance investigations. Her career reached a major milestone when she became Chief Compliance Officer of Webull Advisors before the age of 40, where she successfully built the compliance program from the ground up for the company's startup digital robo-advisor platform.
Today, Ashley is the founder of her own compliance consulting practice, providing fractional and outsourced Chief Compliance Officer services to startup and growing Registered Investment Advisers (RIAs). She helps firms navigate regulatory requirements through RIA registrations, policy and procedure development, testing and monitoring programs, ADV filings, annual reviews, SEC and state exam preparation, and ongoing compliance guidance. Beyond her professional work, Ashley is passionate about giving back to her community and serves as Board Treasurer for the Grounded Mother Project, a nonprofit organization dedicated to supporting mothers through healing, education, resources, and compassionate care during the postpartum journey. Combining technical expertise, leadership experience, and a service-oriented mindset, Ashley is committed to helping organizations build strong compliance cultures while creating meaningful impact both within the financial services industry and beyond.
Her Interview
Ten minutes with Ashley
01What do you attribute your success to?
I attribute my success to hard work, consistency, and really building connections. Networking and feeding those connections is a lot of what has progressed me throughout my career. I think it's about showing up consistently and putting in the work, but also about the relationships you build along the way. Those connections have opened doors and created opportunities that have been instrumental in my growth.
02What’s the best career advice you’ve ever received?
The best career advice I've ever received is don't be afraid to say yes to things you're not ready for. I think people, especially women, are often scared if they don't meet all of the credentials that people are looking for in a job posting. But so much of the job is learned in the job itself, and if you have the foundation and the willingness to learn, I think it's worth taking the leap and challenging yourself. Don't let not checking every box hold you back from opportunities.
03What advice would you give to young women entering your industry?
The biggest piece of advice I would give to young women entering my industry is don't be afraid to say no. I mean that from a capacity perspective. You need to know how much your plate can handle, and if you feel like you have too much, it's okay to say no to something. It's important to understand your limits and not overextend yourself just because you feel pressure to take on everything. Protecting your capacity allows you to do your best work on what you do commit to.
04What are the biggest challenges or opportunities in your field right now?
I think my biggest challenge is getting comfortable in the uncomfortable. I'm in an industry where it's always been primarily men, so being comfortable in those situations that are truly uncomfortable for most people, and just trusting that you have a voice and what you say matters. Don't be afraid to speak up in the silence. It's about having the confidence to know that you belong in those rooms and that your perspective is valuable, even when you might be the only woman at the table.
05What values are most important to you in your work and personal life?
Trust is the biggest value for me. I think if you can build trust, whether it's with your team or your leadership, people will take you more seriously and to heart with what you have to say, whether it's positive or critical feedback. Community is another important value. Having your own personal community that you feel can challenge you, and that you can take things to whenever you are concerned with something, is huge. Leadership is the other key value for me. I think in all capacities, you're acting as a leader. You don't necessarily have to have people reporting to you, but people are always watching, and you want to make sure that you're leading by example.
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