FOUNDER TO THE PROFILE
Jason Caudill
Founder, My Annuity Store, Inc.
“I attribute my success to finding a career I genuinely care about and staying curious throughout it. I’ve spent my entire professional life in the annuity business, and each role taught me something different about how the industry works—and where it can be difficult for consumers to navigate. Starting My Annuity Store gave me the chance to put that experience to work for the people planning their retirement. I’m proud of what we’ve built, but what keeps me motivated is the belief that Americans deserve clear information and real choices when making these decisions.”
About
Jason Caudill is the founder of My Annuity Store, an independent platform built to make annuities easier for Americans to research, compare, and understand. After more than two decades in the insurance industry, he saw a persistent gap between the retirement products available to consumers and the clear, accessible information they needed to make confident decisions. He launched My Annuity Store to help close that gap.
Caudill’s career has taken him across the annuity business. He began as an intern with New York Life while earning his MBA, then joined Standard Life of Indiana, where he worked on the annuity sales desk and later became Vice President of Marketing. He went on to serve as Regional Vice President at Ash Brokerage, supporting advisors across 26 states, and later worked with the Raymond James Insurance Division to help advisors incorporate annuities into their clients’ retirement plans. Those experiences gave him a firsthand view of how annuities are developed, distributed, and explained—and how much harder they can be for consumers to navigate on their own.
Today, My Annuity Store offers access to products from more than 90 insurance companies, with licensed agents serving customers across 47 states. The company publishes educational resources and commission information online, and gives people the option to do their own research or speak with a licensed professional when they want help. It was named a Top Multi-Carrier Annuity Platform by Insurance Business Review in 2025 and 2026.
Caudill earned a bachelor’s degree in business administration and computer information systems from Ferris State University and an MBA in entrepreneurship from Ball State University. He credits much of what he has learned to the people he worked alongside early in his career, and still believes in the advice that guided him then: do the right things every day, keep learning, and treat people well. Outside of work, he enjoys coaching his children’s baseball teams, golfing, and spending time with his family.
Key Areas Of Focus
- 01. Annuities
- 02. Retirement Income
- 03. Direct-to-consumer annuity marketing
- 04. Insurance Distribution
- 05. Consumer Education
IN HIS OWN WORDS
The Q and A
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01
What do you attribute your success to?
I attribute my success to finding a career I genuinely care about and staying curious throughout it. I’ve spent my entire professional life in the annuity business, and each role taught me something different about how the industry works—and where it can be difficult for consumers to navigate. Starting My Annuity Store gave me the chance to put that experience to work for the people planning their retirement. I’m proud of what we’ve built, but what keeps me motivated is the belief that Americans deserve clear information and real choices when making these decisions.
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02
What’s the best career advice you’ve ever received?
The best career advice I’ve ever received was simple: do the right things every day, and good things will follow. I took that to mean learning the products, understanding the industry, and always keeping the people we served at the center of my work. Over time, that approach helped me grow in my career, but it also helped me build relationships with colleagues that I still value today. Titles and roles change; the trust you earn by showing up and doing right by people stays with you.
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03
What advice would you give to young men entering your industry?
My advice is to find an experienced professional you respect and work alongside them early in your career. If you want to be an advisor, start as a junior advisor on a strong team. Learn the products, but also pay attention to how the best people listen to clients, explain complicated decisions, and earn trust over time. I was fortunate to start at a smaller insurance company where I had access to senior leaders early on. Some of my most valuable lessons came from watching how they worked and adopting the habits that made them effective. You can learn a lot in a classroom, but in this industry, there’s no substitute for learning from people who do the job well every day.
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04
What are the biggest challenges or opportunities in your field right now?
The biggest challenge—and opportunity—for the annuity industry is meeting people where they are now: online. Consumers expect to research and compare financial products on their own before they ever speak with someone. At the same time, the industry is navigating changing regulations, growing competition from investment advisors and large financial firms, and long-standing skepticism about annuities. We have to do a better job of explaining these products clearly and earning people’s trust.
On a personal level, building a smaller firm in that environment has taught me how hard it is to find the right talent. I’ve invested in freelancers and contractors for technology, design, and messaging, and not every investment has worked out. But that challenge is also why I started My Annuity Store: I believe a smaller, independent company can make annuities easier to understand and compare online, while still giving people access to a real person when they want help.
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05
What values are most important to you in your work and personal life?
Honesty, loyalty, and hard work are the values I try to live by, both in business and at home. I want people to know they can count on me and trust that I’ll do what I say. My wife and kids are the most important part of my life, and a big part of why I work hard is to provide for them and set an example they can carry forward. I also believe that if you’re in a position to help someone, you should—whether that’s supporting your community or simply taking care of a need without making a big deal out of it. That’s the kind of legacy I hope to leave.
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