Declaration of Independents: Marissa Winkelman

• By: Olivia Overman
• February 28, 2026

Marrissa Winkelman

Managing Partner

Webb + Winkleman Insurance

Grove, Oklahoma

Marrissa Winkelman entered the world of insurance in 2012 when she started as the receptionist at Webb Insurance. Understanding quickly that the position wasn’t the right fit for her, she moved to the back office, where she focused on insurance and working her way up.

By 2023, Winkelman had become a managing partner of the rebranded Webb & Winkelman Insurance Company and set her sights on reinventing the agency’s culture to foster a workplace where women can excel. Two years later, Winkelman was awarded the Outstanding Female Agency Principal award in the Liberty Mutual 2025 Agent for the Future Awards.

“I’m hoping to change the standard for working moms in our industry,” Winkelman says. “That’s really the goal in an industry that used to be so male-led and male-centered.”

Women’s History Month?

We’re planning to do a Women’s Highlight Wednesday where we’re going to highlight quite a few women-owned and operated businesses. Our whole agency is also going to do a women’s hygiene product drive and compile as many women’s hygiene products as we can find, make them into hygiene bags, and take them to Abundant Help, a local charity that helps women and children. We will also celebrate in-house, recognizing the women making a difference.

Agent for the Future Award?

That was probably one of the most incredible moments of my career. It was super meaningful to me because I’m the coach of the team, and it felt like we won the Super Bowl.

Maternity program?

Our maternity program is different from what most people are offered. After I had my son, Lane, I still had to work and was lucky enough that he could come to work with me for the first eight months of his life. Once that happened, the entire maternity program for our agency started, and it has definitely been a culture changer.

The program goes up to six months, and we want to make sure that by month six, we are planning a transition into childcare. Because at some point, we know there’s only so much mom can do.

For the first eight weeks, employees can just take care of themselves and the baby. After that, the baby can be brought into the office, with mom working part-time for four weeks. This allows for an easy, gradual return to work.

In her first month back, Brett, our second employee to take advantage of our maternity plan, hit her goals. She was back into normal sales and renewal calls. Iris is now six months old, and Brett is still hitting her goals. She’s transitioned way quicker than anticipated and has an overall appreciation for the time that she got with her child.

What do you enjoy most about working in insurance?

There’s never a time to get stagnant or to get bored. I’ve been doing this almost 12 years and it’s always changing. And with that, you always have to change and grow and adapt. That’s probably my favorite part of it.

Five years ago, when the market first started crashing, I would not have said that. But going through the last five years really was an experience and it made us have this love for constant change. There’s definitely not a time when I go home and be like, “that was so boring.”

I’m glad that I chose a field that is going to keep things interesting and always on my feet. There’s always a challenge to overcome. And I think that when you’re looking for a career, you’re looking for something that’s going to challenge your brain and keep you witty. And I want to keep being witty.

Typical workday or work week?

Being a working mom is one of the hardest things I’ve ever done in my whole life. I feel like I did a lot before, and then I had my son. We try really hard to make sure that everyone in the agency is able to have a balanced career—when you’re here, when you’re clocked in, we want the best from you and we want you to give it your best. But if you need to leave for an hour to go to your kindergartner’s program, just tell me and go.

We are raising the next generation, and that generation needs consistency from their parents. Our generation may not have had so much, because our parents were always working consistently.

I try to have one-on-ones with the staff every week. There are eight remarkable women in the house, then I have one who is in the Philippines that does data entry for me. And then we have Randy and Christie, the original owners, with whom I’m in constant communication.

Hiring, promoting and retaining employees?

I think our maternity program has shown that retaining our current employees is easier because we have this tool.

As for new hires, we have become a sought-after local employer, where people are approaching us. We’re able to find more amazing women who fit in with us. That’s how we found our last couple of employees—it was more them coming to us versus us coming to them. It’s helped us gain some amazing quality women here, and I think it’s only going to continue to impact our agency as we keep growing.

Giving back?

We do a lot of stuff with the local schools. We’ve gotten pretty lucky last year as we were able to purchase items from the Amazon Wishlist’s from 13 different school districts. We ended up buying one or more item from approximately 62 different teachers.

Our main job is not to save pennies, dimes, nickels or 15 minutes; it’s to educate. It’s to make sure that people understand that this is the risk, this is how we can cover the risk, and this is what we think is best.

But outside of that, we have to remember that we’re all humans, that every person who leaves here is not a robot. Every person who leaves here is a human who has feelings that are valuable. And just seeing them all and trying to make sure that they are seen and understood so that they can continue to give more is important.

Biggest challenges facing insurance agents

Everybody wants something for less. It’s very price-driven. There are some agencies that are okay with that. We need to remember to keep education at the forefront because people are having bad experiences with claims. You’re seeing more disgruntled clients because they didn’t understand what you were selling them.

We have to revert back and make sure we are covering basics, that we are educating clients, and we’re giving them more than just a “Hey, we saved you $20 a month.” We understand that people want to save money, but we can save money without completely stripping someone’s coverage.

Olivia Overman is IA content editor.