For Jeff Caldwell, leadership has always been the heart of his career. After years in finance and insurance, he became a Mortgage Loan Originator in 2000 and knew he wanted to do more than just originating loans. He wanted to build and guide a team. In 2015, that vision brought him to Homestead Financial Mortgage as Branch Manager of our Kansas City office. Since then, Jeff has focused on fostering teamwork, empowering his employees, and creating partnerships that make both his branch and his realtor partners shine. In this Q&A, Jeff shares how collaboration drives daily success, why Homestead’s leadership makes all the difference, and the advice he gives to anyone considering joining our team.
Q: How did you get started in the mortgage industry, and what led you to Homestead in 2015?
A: I spent most of my career in the finance and insurance industries, and in 2000 I began working as a Mortgage Loan Originator. From the beginning, I knew I wanted to do more than originate loans—I wanted to lead a team. I’ve always found it more rewarding to teach people and watch them grow than to focus solely on doing loans myself. In 2015, I came across an opening for a Branch Manager at Homestead Financial Mortgage in Kansas City. I interviewed, and the rest is history
Q: As our Kansas City branch manager, we know working as a “team” is important to you. Can you share a memorable experience or teamwork success story with us?
A: I always remind my team and realtor partners that you’re only as strong as your weakest link, which is why having the right people around you makes all the difference. I let realtors know that if they partner with us, we can make them look like rock stars. At Homestead, our entire operation is built on teamwork.
It’s hard to single out just one success story because every day I see our team come together to make the impossible possible—closing loans that other lenders have denied and helping families achieve their dream of homeownership. Those daily wins are what keep me motivated.
Q: What’s been the biggest hurdle you’ve had to face in lending, and how did you work to overcome it?A: This business is full of daily challenges, and our job is to make the process look seamless for the customer. If I had to choose one hurdle, it would be finding and developing the right employees—people who truly understand the dedication it takes to be successful as a Loan Officer. I’ve worked to overcome this by putting my team first, sharing what I’ve learned over the years, and helping them build the skills they need to succeed. It’s a demanding career, but for the right person, it’s incredibly rewarding.
Q: Reflecting on our mission statement of “Making lives better, one home at a time.” How has working at Homestead helped make your life better?
A: We’re fortunate to have some of the best ownership in the industry. The leadership at Homestead understands the business, trusts us to make decisions, and avoids micromanagement. I’ve always been encouraged to bring new ideas to the table, and many of them have been implemented to strengthen our company. Homestead also provides an excellent work-life balance, which is something I deeply value. I can honestly say I love coming to work every day.
Q: If you could give advice to someone considering joining Homestead, what would it be?
A: Many companies make big promises but fail to deliver. My advice is to talk directly with employees before joining any organization. At Homestead, you’ll quickly learn that the culture, leadership, and work environment are second to none. In my experience, it’s the best ownership and management team I’ve ever worked with, and that makes all the difference.
Jeff’s story is a good example of how the right culture and leadership can transform a career. At Homestead, he has found the freedom to lead his branch with trust, support, and balance, while also making a meaningful impact on both his team and his clients. His passion for developing people and building lasting partnerships reflects what makes Homestead unique—a place where collaboration fuels success.