Brady Cleaveland
Helping You Take the Next Step Toward Retirement Confidence
Life takes unexpected turns, and Brady knows that firsthand. He never envisioned himself working in financial services, but here he is—and he couldn’t be happier. After meeting the Howard Bailey Financial team, he quickly realized it was an environment where he could grow, make a real impact, and expand his knowledge in a meaningful way.
In his role, Brady helps people recognize the importance of asking the right questions about their financial future—many of which they may not have even considered yet. He guides them to the right resources and experts, ensuring they get the clarity and support they need. With nearly six years of customer engagement experience, he has developed strong communication skills that allow him to connect with people and provide real value.
When working with the community, Brady believes in listening first. He is passionate about understanding people’s concerns and goals before offering solutions. His focus is on education rather than selling because he knows that clarity builds long-term trust.
Building relationships is key—it’s not just about one conversation, but about their financial future. Most importantly, he values transparency. If something isn’t the right fit, he’ll be honest about it because integrity is at the core of what he does.
Brady takes pride in his ability to adapt to different roles and industries throughout his career. Each opportunity has helped him grow, develop new skills, and build meaningful relationships. He values his willingness to step outside of his comfort zone and embrace new experiences. Those decisions have shaped who he is today, and he’s grateful for the opportunities that have come from them.
What motivates Brady most is knowing he played a role in helping someone achieve their goals. That feeling is incredibly rewarding and only grows stronger over time. One of his favorite parts of the job is connecting with people who don’t know what questions to ask about retirement. It’s a great feeling when he hears the relief in their voices after introducing them to the resources Howard Bailey provides, knowing that he’s truly helping them prepare for the future.
Outside of work, Brady is passionate about fitness. He also has a deep love for cars and motorcycles—a passion that started when he worked in the automotive industry. If it has a loud engine, he’s all in!
He likes to keep things fun and relatable, even in retirement planning. Don’t be surprised if he throws in a car, motorcycle, or gym analogy during a conversation. After all, success in both requires a solid plan, consistent effort, and a long-term mindset.