10 Young Agents Tell All

In 2016, Neidra Crosby, vice president of The Insurance Exchange in South Holland, Illinois, faced a crisis: Her dad, president of the agency, had a heart attack that took him out of the office for the first half of the year.

“It was like a full-blown dress rehearsal,” recalls Crosby, 36. “We all just stepped up—between myself and my brother, we pretty much had to run the business.”

Ever since joining the ranks at the agency Thomas Sr. started back in 1986, taking the reins was always in the cards for Neidra and her brother, Thomas Jr. “Of course it’s a blessing that my dad’s still with us, and he’s still working and he stayed in it,” she says. “But I think he realized that it was time to set some things up in a way that the succession would be much easier.”

Crosby, who first got licensed while she was earning her Master of Business Administration from Roosevelt University, has “always been into starting my own business,” she says. “I made a decision that I could work for either somebody else’s daddy or my own daddy.”

Every day, millennial insurance agents like Crosby are hard at work making their mark on an aging industry. What brought them here? What makes them tick? And why are they sticking around? Meet 10 millennials who want you to know what they have to offer—and what you need to do for them in return.

NeidraNeidra Crosby

Vice President
The Insurance Exchange
South Holland, Illinois

Age: 36
iPhone or Android? Team iPhone all the way
Favorite streaming service? Apple Music and my Amazon Firestick
What’s in your earbuds currently? My Summer ’17 playlist with some of my favorite songs—“Get It Together” and “Passionfruit” by Drake, “Red Bone” by Childish Gambino and “Humble” by Kendrick Lamar

Why insurance?

I love that every day is different. Some days I’m in the office working hard and trying to put a proposal together, some days I’m servicing, some days I’m out networking and meeting people and representing the agency. It’s also flexible. I’m a mother, so I’m able to be active in my son’s activities and school and set my own income. My greatest goal is to be prosperous in all areas—not just in my career and not just at home. 

Role model/mentor?

Definitely my dad. We learn a lot from him when it comes to just dealing with people and bouncing back. That’s probably one of my biggest lessons from my father—to not let things that seem devastating have a hold over me or change the course. That’s a resilience you can take to all areas of your life. As a young person, the way you respond to life can make or break you.

Industry’s biggest challenge?

The sharing economy. So many people are thinking, “Do I really need to own?” Is that value there for the younger generation? I think some of the traditional ways policies are written and the purpose of them will have to be revisited. With millennials and Generation Z, everybody is just coming up with stuff. In a minute they’re going to be sharing cable. They’re going to be sharing everything. If I can’t afford my car insurance, then eventually, I might just not want a car. And that changes the market. It changes how you do things. At this point, we just have to accept that creativity and start figuring out ways to continue to have insurance working, because it’s the one thing that keeps the economy going.


Corbin Adams

Insurance Broker
Insurers Review Services

Age: 30
iPhone or Android? iPhone
Favorite streaming service? Apple Music
What’s in your earbuds currently? “More Life” by Drake

Why insurance?

My great uncle started the company 35-something years ago, and I felt the opportunity was greater to learn how to be a business person than how to work a conventional 9–5. I kind of blindly did it without much understanding of what I was getting myself into. Fresh out of college, you’re still very wet behind the ears. You notice after a while you’re meeting people in the insurance industry that have more years of experience than you’ve been living. At that point, you just realize you’ve got to be in it in for the long haul. You’re not going to learn it overnight as opposed to what we are accustomed to as millennials—the hot-pocket microwave success. You think you can Google your way through life, and it’s not like that. You have to really pay your dues. It’s not a young man’s game.

Millennial stereotype that fits you?

Technology has created a wedge in understanding between our generation and those before us, because we’re able to process things a lot faster. It’s just that old adage: Work smarter, not harder. Look at something like Fiverr, where you’re able to outsource a lot of functions. Maybe you’re not good at doing an email campaign, but there’s someone out there who can do it for you for a nominal price, and what’s the end result? I could waste my time trying to be proficient at it, or I could be using my time to be looking for other clients.

Next generation of consumers?

A lot of it will have to fold into service. People aren’t looking to do 401(k)s when they have $30,000 over their head in student loans. They’re looking to alleviate that kind of pressure so they can buy homes and their credit-to-debt ratio goes down. As insurance advisers, it’s up to us to provide peace of mind. 

JaredBlackwoodJared Blackwood

President And Account Executive
Bain Agency
Bismarck, North Dakota

Age: 30
iPhone or Android? iPhone
Favorite streaming service? Netflix
What’s in your earbuds currently? Country, country and more country

Perpetuation planning?

It’s been a process from day 1. It took us several years to figure out how we wanted to structure it, how long we wanted it to take, what continued mentorship would look like. I bought into the agency October of last year, so I am 49% owner now. My father-in-law, CEO Steve Bain, is still 51% owner. He is continuing to transfer more and more responsibilities over to me and letting me lead in different areas, learn and grow.

Role models/mentors?

My father worked countless hours, overnight jobs, two jobs, three jobs, to support the family and give us the opportunity and life we had. That work ethic alone taught me you can’t just sit back and expect things to be given to you.

My father-in-law would be the other one, because he’s done the same here at the agency. And not only that—he’s trusted me. You better believe I don’t want to fail because of that. His name’s on the agency and it’s going to stay on the agency, and that makes me want to do better. My whole goal is to leave the agency better than when I came. Long term, I want to have 20 locations. We have one right now. Will I reach my goal? Who knows, but I sure as heck am going to try.

Industry’s biggest challenge?

I often hear from other millennials that they aren’t being empowered. There are a lot of young agents within the industry—we just aren’t being utilized properly. It’s one thing to have a problem attracting young agents in the first place, but when we do get the young agents in here, I think we have a failure of training and mentoring. 

JohnBorjaJohn Borja

Account Executive
Teague Insurance
La Mesa, California

Age: 34
iPhone or Android? iPhone
Favorite streaming service? Spotify
What’s in your earbuds currently? 2Pac

Most annoying millennial stereotype?

That we’re lazy. We’re ambitious and driven. I’ve pretty much built my career from ground zero, and I don’t believe I’m an anomaly. Millennials aren’t going to sit on the sidelines. You either get them involved early and often, or they’re going to move on to another organization and contribute there. We have an opinion and we’re going share it, whether it’s unsolicited or solicited.

Millennial stereotype that fits you?

We don’t believe in the status quo. We’re challenging the establishment. We’re saying, “Wait a minute—I know it’s been going on since long before I was born, but is this the proper way of doing it? Is there a way to make this better for the industry?”

Next generation of consumers?

With millennial business owners, you have to pinpoint something that’s going to make them think. “How are you addressing minimum wage in California? How many harassment lawsuits have been filed against you?” All of a sudden you got their attention—they’re like, “Oh wow, we just had a lawsuit on that stuff.” And you tell them, “Look, it’s very common, we see it all the time, so I’m just letting you know that this is what it does to a person or a business. I’m not trying to give you a magic wand for everything. I’m just telling you how you can adjust some procedure internally to reduce your exposure.”

The industry’s always grinding people to sell, sell, sell, sell. And yeah, we know that’s how we survive, but that’s not going to help attract clients or improve our standing. Sometimes it feels like it’s sales before advising the client, or commission before duty of care. We have to condition the millennials, but at the same time we have to bring value to them. We have to show love. The money will come with that. 


Ashley Fitzsimmons

Insurance Specialist
Fitzsimmons Insurance Agency, Inc.
Forest City, Pennsylvania

Age: 28
iPhone or Android? iPhone all the way
Favorite streaming service? Netflix
What’s in your earbuds currently? Billy Joel’s Greatest Hits. Just saw him in concert—so good!

Why insurance?

One instance that sticks out to me is when somebody’s cabin burned down. It was a secondary residence, but I knew the guy pretty well—I knew his kids, they came in all the time. I took Dunkin’ Donuts coffee and donuts up there when the adjuster was going to meet them—it was pouring rain that morning.

Two years later, he still thanks me. I get teared up just thinking about it because I know that was traumatizing and I felt so bad—I just wanted to be there for them. I don’t ever want to look in a file and say, “Hmm, I don’t know who this person is.” I want to be able to say, “How’s your kid doing? How was his baseball game? How’s your dog?” 

Millennial stereotype that fits you?

We’re not necessarily focused on making a ton of money. Trust me, I want to have the funding and the ability to do whatever I want, whenever I want. But instead of taking a raise, maybe I’d rather put that money toward attending more conferences and making more connections. I would rather go out and experience things.

Industry’s biggest challenge?

It’s a challenge to keep everybody from jumping ship. When you have a problem,
you could call an 800 number and talk to five different people, or you could call Fitzsimmons Insurance and talk to me. But it’s hard to sell an intangible product. You don’t want to have to convince them after the fact. You don’t want them to ever come to you and say, “Oh man, I wish I listened.” You need to be passionate enough about it upfront that they realize, “You know what, you’re right—I do need this to protect my family and my future.” 


Jaime Hopkins

Insurance Agent
Hopkins Insurance, Inc.
Pocahontas, Iowa

Age: 25
iPhone or Android? iPhone
Favorite streaming service? Spotify
What’s in your earbuds currently? Eric Church

Why insurance?

My mom started the agency when I was young, so throughout high school, I would go in and do little things for her. I went to college and came back almost every summer and worked for her. I got licensed when I was a junior. I majored in animal science and agriculture—a lot of our clients are farmers, so I have knowledge of what they do.

Industry’s biggest challenge?

I do mainly crop insurance, and there is a lot going on there that’s always kind of up in the air. Right now they’re trying to push something called the Acreage Crop Reporting Streamlining Initiative (ACRSI). A farmer will usually certify their acres at the Farm Service Agency (FSA) office, and then they’ll bring us the FSA forms and we insure their acres based on what they reported to the government. ACRSI is trying to eliminate the steps where they go to the FSA office so that instead they just report their acres directly to us, because they’re afraid the FSA is going to try to take over the crop insurance agent part. But I just don’t see how that works. It’s a whole other step and process, and it’s already super busy during acreage reporting time. I can’t imagine adding that step to it. And I don’t think it’s wise for us to try to take their jobs too, because that would prove that just one person could do this.

Role model/mentor?

Definitely my mom. I feel like friends and family never really want to sit and talk about insurance or things that we find dramatic or interesting, but we have that in common. I like listening to her insurance stories. We can go back and forth. 


Corbin Jackson

Oklahoma City

Age: 24
iPhone or Android? iPhone
Favorite streaming service? Spotify
What’s in your earbuds currently? Lecrae

Why insurance?

My father’s been in the industry for 35 years as a Farmers agency owner, so I grew up in the agency system and in the industry in general. At the beginning of college, after really analyzing the industry and the potential there, I decided it was a good direction to go with my skills and the relationships I had within the industry already. I majored in insurance and risk management at ­University of Central Oklahoma and was chapter president at Gamma Iota Sigma, the collegiate fraternity for risk management, insurance and actuarial science. I went to work for a ­broker out of college for a couple years and then started my own independent agency.

Why go it alone?

It comes down to my entrepreneurial spirit, being that competitive person and wanting to not necessarily reinvent the wheel, but add a different flavor to it than some of the older models. In Oklahoma, I sensed an opportunity with the smaller and middle-market commercial accounts to have a more high-touch service type of model. You’ll probably hear from a lot of millennials that we want to do the technology thing and automate a lot of processes. And I think that’s good in some areas, but depending­ on the types of clients you work with, I think it’s equally good to be hands-on and understand their goals short- and long-term, and then reverse-engineer that to create an insurance program that accomplishes their goals in business.

Industry’s biggest challenge?

A lot of investment and venture capital money is going into these InsurTech startups, which brings new challenges and opportunities. It’s actually a great thing from a capitalist point of view—if we become obsolete, that means we didn’t do our jobs, right? Now more than ever, independent agents need to identify what they’re really good at and double down on it. Forget about the rest. Be the best at what you do.


Owen Thomas

Agent and Senior Account Executive
Dial Insurance Agency
Pembroke, North Carolina

Age: 29
iPhone or Android? Team iPhone
Favorite streaming service? Pandora
What’s in your earbuds currently? Today’s Country Radio

Why insurance?

I finished up graduate school with the thought of either being in some sort of sales/marketing position or going to get my doctorate. I decided to go the sales route and started working for a publication firm that did professional relocation guides and membership directories. After about four projects moving hotel to hotel, I got tired of getting into a community and having to leave immediately without creating relationships.

I’m actually the president now, but at the time I was a member of the University of North Carolina at Pembroke Alumni Association board of directors. One of my fellow board members had the largest agency in the county, and he said, “If you’re thinking about a career change, let me talk to you about insurance.”

Role model/mentor?

Definitely my boss, Jarette Sampson. For a month straight when I first got here, he would take me on all his sales, and if I had sales he would come and sit down and help me out if the client had any questions I didn’t know how to answer. He kind of put me in his pocket.

Next generation of consumers?

I teach management and marketing classes part time at the university, and something I’ve learned there is that students aren’t learning how to create relationships or create the opportunities necessary for them to become successful. A lot of times in college, students aren’t surrounding themselves with the right people. Maybe they’ll have mentors, but understanding how to connect with different generations, different people, diverse groups—it’s kind of going downhill a little bit. If I could give any advice to someone coming up, a young star, you’ve just got to keep continuing to build relationships and sell yourself. Show people how you can become valuable to them. 


Aislyn Vaughan

Commercial Lines Account Manager
St. Albans City, Vermont

Age: 26
iPhone or Android? iPhone
Favorite streaming service? Spotify or Netflix
What’s in your earbuds currently? “Bring Your Love to Me” by The Avett Brothers

What do you love about insurance?

Vermont is made of small businesses. It’s buy local, shop local. We don’t even allow Target in our state. So many people have more than one job. I’m a yoga instructor and a dance teacher as well—it’s just part of our community. It’s the way we function here. I go from contractors to waffle stands at farmers markets to boat washes to dance teachers to nurses. My book of business is all over the place.

Millennial stereotype that fits you?

Have you ever heard the Ralph Emerson quote, “What lies behind us and what lies before us are tiny matters compared to what lies within us”? I think that’s so us. We’re made of something else. We’re willing to get the work done to make our customers or clients happy—we’re just not willing to give up who we are as a person. My parents immigrated here from Ireland in their early 20s to give us greater opportunities. They made things happen for us just by moving here and supporting us, no matter what the dream was. Why wouldn’t we want to take advantage of that?

Industry’s biggest challenge?

We have a lot of people retiring at a very fast rate, and we don’t have people filling those positions. If you’re only willing to hire people with three to four years of experience, you’re going to find yourself without a staff. Agencies need to put the work in to recruit people who will want to make this a life career. Millennials want to feel challenged and inspired. We want to know our work is fulfilling and has a purpose and makes a difference in someone else’s life. We don’t want to sit there and feel like we’re just a cog in a machine. 

RachelVela2Rachel Vela

Insurance Consultant
Vela Insurance Agency
Lakewood, Colorado

Age: 26
iPhone or Android? Android
Favorite streaming service? Spotify and Netflix
What’s in your earbuds currently? Spotify’s Badass Women playlist

Why insurance?

It definitely wasn’t my dream career when I was younger. I never even wanted a desk job, actually. I did a year at University of Northern Colorado in Greeley and I didn’t really know what I wanted to do, so I was like, “I’ll just take a break, and if I want to come back, I’ll come back.” Then I had some odd jobs, restaurants mainly, and it just felt like a dead end.

This is my mom’s agency and she kept telling me, “Come try it, just for a year.” I was really hesitant because when I was younger she’d always bring me and my sister into the office, and we hated the office. But I was like, “All right, fine. I’ll give the desk job a chance.” That was about five years ago, and I’m still here.

What keeps you in it?

With some of the jobs I had before, I found myself counting down the hours. It would get so boring, being at a restaurant where it’s not busy and you’re literally doing nothing for probably hours. Insurance is challenging. It’s not what I thought it was going to be.

Role model/mentor?

Definitely my mom. She’s been doing this for 20–25 years, so she knows the ins and outs of insurance and life. And everyone in the office, we’re always talking to each other and learning from each other. We try to bring more fun things into the work environment, too. All those big places like Google, they have all these cool things they have going on at work to help you de-stress. We always have little birthday celebrations, or we’ll go bowling after work, and we did an Easter egg hunt recently with some games. It’s a big team effort we’ve got going on. We all know we all count. •

Jacquelyn Connelly is IA senior editor.