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Jason Caudill, MBA: Annuity Expert and Founder of My Annuity Store

Twenty years inside the annuity industry, over $1 billion in annuity premium placed during his career, and one goal: make retirement income easier to understand and easier to compare.

Updated September 19, 2026 Hamlet, Indiana
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Jason Caudill, MBA, founder of My Annuity Store

Who Is Jason Caudill?

Jason Caudill, MBA, is the founder of My Annuity Store and an annuity expert with more than 20 years in the annuity and retirement income industry. He has worked for an insurance carrier, a national brokerage, and a Fortune 500 wealth management firm, and during his career he has placed over $1 billion in annuity premium.

Why Annuities Became His Life's Work

Jason Caudill started his annuity career in 2005 as an intern at New York Life while earning his MBA. There was no single moment that made annuities his life's work. It happened the way real understanding usually does, one layer at a time.

People often describe three stages of learning: memorization, learning, and internalizing. Jason went further down that road with annuities than with anything else in his life. Early on he memorized the products, then he learned how and why they work.

The third stage came at Standard Life Insurance Company of Indiana. Somewhere along the way he internalized what annuities actually do: turn a lifetime of savings into income a person cannot outlive, something no other financial product can guarantee. From that point on, it stopped feeling like selling and started feeling like explaining something people genuinely needed to understand.

That conviction has carried him through two decades and nearly every seat in the annuity industry. It also showed him the problem. The products that deliver safe, dependable income exist, but they are too often wrapped in jargon, hard to compare, and explained only at the end of a sales conversation.

The lesson he took from all of it is simple. Annuities are not right for everyone, and they are not magic. But matched to the right goal, they can solve one of retirement's hardest problems: turning savings into safe retirement income that lasts as long as you do.

Jason Caudill's Professional Background

Jason's career has given him a view of the annuity industry from four sides: the insurance carrier, the brokerage general agency, the wealth management firm, and the consumer. Each role taught him something the next one needed.

2020 to Present: Founder, My Annuity Store

Jason brought everything he had learned to My Annuity Store, an independent annuity platform built for consumers first.

June 2017 to July 2021: Regional Marketing Director, Raymond James

Jason joined the annuity division of Producers Choice Network, where his main account was Raymond James. When Raymond James acquired Producers Choice Network, he stayed on as Regional Marketing Director for the Midwest, working out of the Detroit office alongside an annuity specialist at the firm's Florida headquarters. Inside a Fortune 500 wealth management firm, he saw how retirement income decisions are made at scale.

May 2009 to March 2017: Regional Vice President, Ash Brokerage

At Ash Brokerage, one of the largest brokerage general agencies in the country, Jason ran regional annuity distribution. He worked with independent agents across fixed annuities, fixed indexed annuities, MYGAs, and income riders.

2007 to 2009: Vice President of Marketing, Standard Life Insurance Company of Indiana

On the carrier side, Jason led marketing for Standard Life Insurance Company of Indiana. He learned how fixed annuities are designed, priced, and brought to market. It is also where annuities stopped being a product to him and became a conviction.

2005 to 2006: Intern, New York Life

While earning his MBA, Jason started his annuity career at New York Life. It was his first look at how guaranteed income products work and how the people buying them make decisions.

Why He Built My Annuity Store

After years inside the industry, Jason reached a conclusion. The problem was never that annuities were bad. The problem was that most people had to evaluate them without clear, current, comparable information.

Annuity rates were hard to find. Surrender charges, caps, and income rider terms were buried in brochures. And most research started with a sales call instead of ending with one.

My Annuity Store launched in 2020 to change that order. Because Jason was still at Raymond James, his wife Kiara Caudill earned her insurance license and launched the business while he supported the family. Kiara is CEO of My Annuity Store, and the company would not exist without her.

Today the platform publishes current annuity rates from 90+ top annuity companies, plain-English product reviews, carrier research, and free calculators. My Annuity Store has placed $130 million+ in annuity premium since 2020 and was named a Top Multi-Carrier Annuity Platform by Insurance Business Review in both 2025 and 2026.

The belief behind it is simple: people deserve clear, current, useful annuity information before anyone asks them to make a decision.

"Clients shouldn't have to be a lead before they can learn. We prefer they learn everything before they call us, and the more they can learn, the easier it is for us."

Jason Caudill, in Insurance Business Review (2026)

Areas of Annuity Expertise

  • Fixed annuity rates. How guaranteed rates, terms, and surrender schedules work, and how to compare them.
  • MYGAs. Multi-year guaranteed annuities and how current MYGA rates stack up against CDs and Treasuries.
  • Fixed indexed annuities. Caps, participation rates, crediting strategies, and what an FIA can and cannot do.
  • Income riders. Roll-up rates, payout percentages, and when a rider is worth its fee.
  • Retirement income planning. Turning savings into a dependable paycheck.
  • Social Security optimization. How claiming age changes lifetime benefits and how annuities can bridge the gap.
  • Safe-money strategies. Principal protection for people who cannot afford a market loss near retirement.
  • Annuity company research. Financial strength, product filings, and carrier-by-carrier comparisons.

Education

Awards and Recognition

Media Citations and Publications

Jason and My Annuity Store have been cited by national financial media and industry press. See the full list on the My Annuity Store press page.

"Annuities are one of the most important purchases a retiree will ever make, and for a long time the only way to get real numbers was to sit through a sales pitch. We wanted to flip that. Everything we've built over the past six years comes back to one idea: clients shouldn't have to be a lead before they can learn."

Jason Caudill, in My Annuity Store Named Top Multi-Carrier Annuity Platform for Second Consecutive Year (September 2026)

Companies and Projects

My Annuity Store

Founder, 2020 to present. An independent annuity platform with current annuity rates, MYGA rates, carrier reviews, and retirement income tools from 90+ top annuity companies.

Andy Annuity

Creator. Andy Annuity is a free AI annuity research assistant that searches carrier brochures and live MYGA rates to answer questions in plain English. Andy is an education and research tool, not a substitute for personal advice.

JasonCaudill.com

Jason's personal site, with original research and commentary on annuity markets.

Outside of Work

Jason lives in Hamlet, Indiana. He is a father of three, coaches his kids' baseball teams, plays golf whenever he can, and loves to travel with his family.

Whether he is coaching a youth baseball team or explaining a retirement income strategy, his approach is the same: start with the fundamentals, remove the confusion, and let people make confident decisions.

A Note From Jason

I've spent my whole career around annuities, and I still believe in what they can do when they're used for the right reason. What I don't believe in is making people decide without the facts in front of them.

That's why we built My Annuity Store the way we did. Current rates are public, the fine print is explained, and nobody has to sit through a pitch to learn how something works. My goal is simple: help people make retirement income decisions without feeling overwhelmed, pressured, or talked down to.

Jason Caudill, Founder

Connect With Jason Caudill

Journalists, researchers, and anyone doing their homework are welcome to verify Jason's background and follow his work.

Frequently Asked Questions About Jason Caudill

Who is Jason Caudill?

Jason Caudill, MBA, is the founder of My Annuity Store and an annuity expert with more than 20 years in the annuity and retirement income industry. During his career he has placed over $1 billion in annuity premium.

How long has Jason Caudill worked in the annuity industry?

Jason started his annuity career as an intern at New York Life in 2005 while earning his MBA. He has worked in the annuity industry for more than 20 years.

What is My Annuity Store?

My Annuity Store is an independent annuity platform founded in 2020. It publishes current annuity rates from 90+ top annuity companies, product reviews, and free retirement income calculators.

What types of annuities does Jason Caudill specialize in?

Jason focuses on fixed annuities, MYGAs, fixed indexed annuities, and income riders. His work centers on safe retirement income and Social Security timing.

Has Jason Caudill worked with major insurance or financial services companies?

Yes. Jason has held roles at New York Life, Standard Life Insurance Company of Indiana, Ash Brokerage, Producers Choice Network, and Raymond James.

What is Andy Annuity?

Andy Annuity is a free AI annuity research assistant built by My Annuity Store. It answers questions using carrier brochures and live MYGA rates.

How can I compare annuity rates on My Annuity Store?

Visit the annuity rates page to compare current fixed annuity and MYGA rates by term and carrier. You can also request a free annuity comparison at no cost.

Latest Articles by Jason Caudill
What the Fed Rate Hike Means for Annuity Rates The Battle Over Fixed Index Annuity Illustrations AM Best Puts Delaware Life, Clear Spring and Gainbridge on Negative Outlook: What It Means for Annuity Owners Lottery Payout Options: Annuity vs. Lump Sum (2026) Annuity Sales Hit $461 Billion in 2025 | Demand Continues Best Annuities for a Social Security Bridge (2026)

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Disclaimer: This page describes Jason Caudill's professional background and is for informational purposes only. It does not constitute financial, tax, or legal advice. Awards and media citations listed above refer to My Annuity Store unless noted otherwise.

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