February 26, 2024

Stephenson Insurance Group open for business

At 605 West McLane Street, in the space formerly occupied by Teri Johnston with State Farm Insurance Agency, insurance seekers can now find Stephenson Insurance Group, headed by former Osceola resident and 2002 graduate of Clarke Community Schools, Josh Stephenson.

With the official opening of Jan. 3 now in the books, Stephenson sat down to chat about how he is happy to be back in Osceola, reconnecting with people while providing quality service and education about insurance to buyers.


Born and raised in Osceola, Stephenson has many fond memories from growing up here. He spent his summers swimming in the old pool on the east side of town, riding his bike all over, and playing at the old ball fields.

“A ton of awesome childhood memories here,” said Stephenson.

After high school, Stephenson attended Northwest Missouri State University in Maryville, Missouri, where he majored in business management and marketing.

When he graduated college, Stephenson jumped headfirst into the insurance industry, and has been there since.

“I really didn’t set out to get into the insurance industry, it just happened to be my first position and then kinda fell in love with the industry,” said Stephenson.

Stephenson spent 10 years with Nationwide Insurance in Des Moines, working in areas such as claims, sales, and underwriting, plus a variety of different leadership roles.

Wanting a change of pace and more customer interaction, Stephenson moved over the agency side of insurance, spending the next seven and a half years at Midwest Heritage Agency in West Des Moines. There, he led an insurance channel selling home, auto, commercial, farm, ranch, life, disability, and more to consumers.

“[It’d] always been a lifelong dream to own your own agency…you never know how or when or if it’s going to happen,” Stephenson said.

One thing he did know, however, was that when the time did come, he wanted to open his own agency in Osceola. When the opportunity to do just that presented itself, Stephenson jumped on it.

“This is what suits me. I love southern Iowa people, being back where I grew up, all these old connections,” said Stephenson.

The agency

As an independent agenct, the products offered by Stephenson are not tied to one specific insurance provider, offering a better range of options to the customer.

“We take whatever needs you have, and take them out and explore the marketplace…it’s a one-stop shop,” Stephenson said.

If a customer has questions about billing or claims, they can come directly to Stephenson as opposed to calling an insurance company or trying to find an answer online.

“We help you from start to finish, and then take care of you once you become a client,” said Stephenson.

Another plus to using an independent agent versus a company is that if the product you have is no longer relevant to you - perhaps the rates are not good enough or the insurance company is no longer willing to insure you - you have options to go somewhere else, and not have to figure it out on your own.


For Stephenson, educating people on what insurance they need and what they are purchasing is important element to him.

“What I get the most pride out of is walking somebody through an insurance quote and explaining…allowing them to choose what best suits them, and helping them understand how those coverages actually apply in reality,” said Stephenson.

Purchasing insurance is not just a one-way street, and Stephenson said the best path for success is participation from both the agent and the customer. It’s not just the product you’re purchasing, but the service, trust, and relationship with your agent in person, in real-time.

“[For] southern Iowa people, it’s still a relationship,” said Stephenson.

Meet the agent

Stephenson resides in West Des Moines with his wife, Emily (a compliance consultant at Nationwide), and their three boys: 7-year-old Jack, 5-year-old Ben, and 3-month-old Luke. When not at work, Stephenson said that most of his time is dedicated to spending with his children and their activities. They enjoy swimming and being involved in all of the rec activities available to them, with Stephenson pitching in to coach where he can.

“We’re big believers in if you want to be involved in an activity, get involved,” said Stephenson.

And when it comes to working back in his hometown and seeing familiar faces, Stephenson couldn’t be more ready or excited.

“I’m extremely excited to be back. I feel like I’ve been gone up in Des Moines, but it doesn’t take long once you’re back…It feels good to be back,” said Stephenson.

Candra Brooks

A native of rural Union County, Candra holds a Bachelor's Degree in English from Simpson College and an Associate's Degree in Accounting from SWCC. She has been at the Osceola newspaper since October 2013, working as office manager before transitioning to the newsroom in spring 2022.