Some people walk into the insurance industry through a referral or a career fair. Marrissa Winkelman walked in through a second chance — a receptionist job she didn’t even get the first time she applied, at a three-person agency in Grove, Oklahoma, that took a shot on a self-described wild card at twenty-four years old.
Eleven years later, she’s a co-owner of Webb Winkelman Insurance, running what she lovingly calls her “girl gang” — eight women of different ages, backgrounds, and life stages who show up every day and, in Marrissa’s words, just get each other. She was recently featured in Independent Agent Magazine under the headline Declaration of Independence. She won the Safeco Outstanding Female Principal award in her first year as principal. And she built an agency culture so intentional that babies have come to work, every other Friday ends at noon, and the waiting list to join the team speaks for itself.
None of it happened by accident. And none of it was easy to get to.
Six Generations. One Decision.
When I asked Marrissa where her drive comes from, she didn’t hesitate.
“My mother is an addict, and she is still in active addiction to this day. My mom had me at 16, her mom had her at 16. There’s a lot of abuse, a lot of addiction… My dad was my saving grace. He was a very driven, hardworking man.”
Her father finished raising two girls on his own. Marissa was fourteen when her mom left the picture entirely. Her sister was seven. From that point forward, her dad made sure she had bills to pay — car insurance at sixteen, responsibility before she had any business having it — and cheered her on louder than the statistics cheered against her.
She comes from six generations of addiction on her mother’s side. She said it plainly, without drama. And then she said something that stopped me cold.
“I grew up in chaos. I grew up in loud chaos, and so the violence it took to get to this calm is so wonderful. I have peace and I have calm in a way that I didn’t think when I was a child that I would ever have.”
She’s not interested in using her past as a crutch. She knows people do — she’s watched it happen with family members who are still running that course, letting where they came from become the reason they stay stuck. That’s never been available to her as an option.
“There’s something in me that’s like, you weren’t born to be like them. So sometimes you just got to change, right?”
Hire the Ones With Something to Prove
Marrissa has never hired a licensed insurance professional. Every person on her team came in without industry experience — waitresses, a daycare teacher, people who were handpicked or found their way to the agency because they wanted to be there.
Her hiring philosophy is unconventional, and she’ll tell you exactly what she’s looking for in an interview.
“Nine times out of ten, if I am interviewing and they start talking about their children, I know right there that they have a drive that is just indescribable. Like indescribable to have the drive of being a working mother.”
She’s not hiring credentials. She’s hiring fire. The hunger that comes from having something to prove — to yourself, to your kids, to everyone who counted you out.
“You look for the ones that have something to prove because they’re going to work hard for it and appreciate it. And for me, I’ve had something to prove my whole life, and I’ll have something to prove until I get to heaven’s gates.”
It’s not a coincidence that the philosophy she uses to hire mirrors the story she lived. She was the wild card who got a second chance. Now she gives second chances. The cycle — this one, at least — she’s very intentional about repeating.
A Partnership That Was Worked In, Not Bought In
About eight months into her time at the agency, the owners noticed Marrissa was doing more than receptionist work. She was selling. They pulled her back, brought in someone else for the front desk, and she kept building.
Then a marketing rep came through — someone who noticed something the owners might not have fully seen yet — and pulled Randy and Christie aside.
“He was like, ‘You got to lock her in one way or another. You need to lock her in.’ And that next year at my anniversary, I was actually gifted a percentage of the agency.”
She didn’t buy in. She worked in.
When Randy and Christie made that decision, Marrissa says they weren’t losing anything — they were elevating what they’d built. That reframe matters. A lot of agency owners hold equity close out of fear of losing what they’ve created. What happened at Webb Winkelman is a case study in what’s possible when the founders see it differently.
“When Randy and Christie brought that to me, it was not that they were going to lose anything. It was that they were elevating it.”
When You’re a Coach, You Don’t Get to Swing
Marrissa will tell you that the hardest part of where she is now isn’t the carrier conversations or the retention numbers or the data. It’s the identity shift.
She loved producing. She loved the grind of it — the busy seasons, the quotes flowing, the relationships she was building one chinchilla story at a time. Moving into a leadership role meant giving that up, and she’s still working through it.
“It’s a tricky thing because you’re so used to playing on that team and you’re up to bat. And when you’re a coach, you don’t get to swing. You have to make sure that all of them are swinging correctly.”
Her day now looks like checking in with each person on the team, making sure their plates are manageable, redistributing when someone’s overloaded. She calls herself the ringmaster of a perfect circus. She just went ten days on vacation and handed the agency off to one of her team members before she left — lists, expectations, authority to run it. It worked.
The advice she’d give to herself years ago, stepping into management for the first time:
“Create the space that you want to live in. As a manager or leader of any sort, you do have a say so in the culture that you are in. Make the culture that you want, create it, change it. Don’t take no — sit down. Always go for the yes, even when you get the no’s.”
The Girl Gang Is the Point
Webb Winkelman has a maternity program that Marrissa describes as “out of this world.” When she was pregnant with her son Lane, he came to work with her for eight months. She didn’t have to choose between her baby and her career — she brought them together, and it changed her. Since then, two more babies have done the same. One of them, Iris, spent her first six months in the office.
Eight women. Different ages. Different stages. Some have kids, some don’t — and Marissa is clear that the culture extends to everyone. Starting April 1st, every other Friday ends at noon.
“The world doesn’t work for working moms as it is. School is from eight to three. Moms are from nine to five. They don’t work for us. We just got to make spaces in that area.”
She’s not waiting for the industry to figure this out. She built the space she wanted to lead in, the same way she built herself — deliberately, stubbornly, and with a lot of love for the people she’s doing it with.
You can connect with Marrissa on LinkedIn and learn more about what she’s building at Webb Winkelman Insurance.
At ia Blueprint, we work with agency owners who are ready to build a team that lets them step into the leadership role their business actually needs. If you’re still doing everything yourself and wondering how to make the shift from player to coach, book a discovery call. Let’s talk about what’s possible.