Learn what this next generation of agents has to say about what brought them to insurance, where the industry is headed—and how they fit into it.
Nineteen years old, with an associate degree in art and uncertainty over her career, Kristi Sizemore moved back to her hometown of Holgate, Ohio. Her parents told her about a local insurance agency—Frost Insurance—that was hiring a customer service representative (CSR).
“So, I was like, 'Why not?'" Sizemore, now owner and agent at Frost Insurance, recalls. “I was already familiar with insurance because, when I was getting my art degree, I worked at Nationwide Insurance during the day and UPS at night. I'm not sure how I juggled all that, but it did prepare me for being a mom and owning a business."
Sizemore started her career at the agency answering phones before becoming a licensed CSR. But when she hit her mid-twenties, she realized she wanted more out of the insurance industry.
“I went to my boss and said, 'I could see myself in this industry long-term—what can I do to be successful?' He transitioned me to the role of agent," Sizemore says. When she was offered an ownership position at Frost Insurance, which she part-owns alongside four others, “it was surprising and exciting to me since I came from a background of art," she says.
By becoming an agency owner, Sizemore joined a small club of women in leadership in insurance agencies. Only 26% of insurance agency owners or principals are women, according to Liberty Mutual and Safeco's 2024 Agent for the Future research—a decrease from 31% in 2022.
Sizemore's biggest piece of advice to other young women seeking leadership positions is to embrace authenticity. “Even though there are stereotypes within the insurance industry, I have never changed who I am or how I've conducted myself," she says. “That is true for everyone—we recently hired a young male agent, and the advice I gave him is, 'You need to find who you are and what type of salesperson you're going to be because I don't want you to mimic anyone. That's not who you are—and people are going to be able to tell.'"
She encourages women already in leadership to advocate for others, emphasizing the importance of mentorship and community. “Men can be roadblocks to including women in insurance—I've witnessed it, I've experienced it—but women can hold other women back too," she says. “We need to stand together and elevate each other. If we do that, I think we'd see a lot more women in insurance leadership positions."
Every day, young agents like Sizemore are making their mark on the insurance industry. What brought them here? What makes them tick? And why are they sticking around? Learn what this next generation of agents has to say about where the industry is headed—and how they fit into it.
Owner and Agent
Holgate, Ohio
Age: 35
Go-to drink order: Coffee in the morning, cabernet at night
No. 1 item on bucket list: Travel to Morocco
Favorite candy: Skittles
Art carryover?
I think my personality is fun and creative and spunky and different. I don't think in black and white. I think that's why I can relate to people on a different level than others, and that's why I've been successful. I'm also doing marketing for our agency. I did end up getting a business degree.
Role model or mentor?
My Aunt Judy, who is actually my husband's aunt, worked at Nationwide and got me that job when I was in college. I always admired her and her work ethic, and especially how she presented herself. She wasn't a woman trying to be in a man's position. She proved herself with her actions—from the way she walked and talked to the way she built her knowledge.
I struggled with finding a mentor early in my independent insurance agency career because I was so young. When I became an agent, I looked around the room; there weren't many other women around. As I've grown older and more comfortable networking, and as the amount of women agents has increased, I've found more of a community. I've also become very close to one of the partners that owns the agency with me, Rachel Moll. We can relate to obstacles that we deal with within the industry.
Work-life balance?
As a mom and a business owner, being a mom is No. 1. Work-life balance is huge, and something that's really important is that I have a husband who is supportive, and we can lean on each other. We're both in sales, and we understand that some days one of us may come home and be super spent and need a rest, and then the next day that person can pull their weight a little more.
Senior Vice President, Public Entity and Social Service
Meriden, Connecticut
Age: 31
Go-to drink order: Manhattan
No. 1 item on bucket list: Drive a lap on the Nürburgring
Favorite candy: Andes
Biggest industry challenges?
Being in the insurance industry, we see the good that the industry brings. It's an important function of our society. Internally, we see this as a noble profession. From the outside looking in, every other week it's someone posting on social media that insurance is a scam. I think it's incumbent upon us as agents and brokers to provide education and let people know, “Hey, this is why your auto premiums are increasing 30%-40%—here's really what's going on."
Role as chair of Big I Connecticut NextGen?
Working with the NextGen folks is an incredible experience because it's a body within the industry that's growing rapidly. There's this huge generational shift that's going to be occurring within the industry over the next 10 years. We're going to see a “silver tsunami" of folks in the industry looking to retire. We're going to have a huge wave of young talent coming into the industry, and that's exciting. To see it firsthand working with NextGen has been an awesome experience.
Future of the industry?
I'm really curious to see how artificial intelligence (AI) is going to interplay within the industry. I don't think that AI is necessarily going to replace roles within companies, but I think it will enhance underwriting, writing emails and things like that.
The other change I see in the future of the industry is that generational shift. I think it'll be good for the industry to give the younger generation an opportunity to take up the crown and push forward.
Megan Kempf
Agency Manager
New Athens, Illinois
Age: 29
Go-to drink order: Ice-cold diet Dr. Pepper
No. 1 item on bucket list: I'm a redhead, so my dream has been to travel to Ireland on St. Patrick's Day
Favorite candy: Hershey's bar with almonds
How did you get started in insurance?
I worked for a hospice company for many years. I was attending night school to be a nurse and I hated it. I wasn't happy. I was trying to pay my way through school, working and taking one or two classes each semester. I realized there was no way I was ever going to get done with school. I had an interview with Allstate but being a captive agent was not the route I wanted to go. I liked the flexibility of the independent agents. My uncle owned—and still owns—Matzenbacher Insurance Agency, and he mentioned he was looking for a new employee. I've been here ever since, and I now manage the agency. I really enjoy it.
Industry challenges?
We've been handed major challenges in the last two years—rates, restrictions and retention. It's more difficult to move business and retain customers and keep everybody happy.
Involvement in the Big I Illinois Young Agents Committee?
It's been so beneficial to be able to work with other young insurance professionals. I'm looking forward to connecting with others across the state. Being able to bounce ideas off of other young agents for marketing, retention and other business strategies is really nice.
Nnamdi Anene
Client Risk Advisor
Atlanta
Age: 25
Go-to drink order: Tequila and soda with a bunch of limes
No. 1 item on bucket list: Travel—I'd love to go to Switzerland or Nigeria
Favorite candy: Anything sour
Why did you choose insurance as a career?
At the University of Georgia, I took classes on various business types and I found the Intro to Risk Management class to be pretty intuitive. In my research, I saw there were many different avenues you can take in insurance and that flexibility was attractive.
Mentoring others on the state young agents committee?
One of my main mentors at our firm guided me in the direction of the Independent Insurance Agents of Georgia Young Agent Committee (IIAG YAC) and told me how important it was going to be to start getting involved at a young age. I have the opportunity to meet a lot of different people and mentor younger folks just getting into the industry—whether it's reaching out a couple of times a quarter or grabbing coffee and seeing where they're going. I also get the opportunity to meet older, more established people in the business and talk to them. My mom always told me to learn from other people's mistakes and not your own, so I make sure to ask what worked for them, what didn't, and how they paved their own path.
Goals for the future?
With Sterling being privately held, one of my main goals is to eventually become a shareholder and a partner there. I want to inspire the younger generations as they come up and to become a role model to others. I want to be able to support my family—they've always been a big supporter of me and my dreams, and I would love to give back to them one day on a bigger level.
Maggie Landry
Director of Personal Lines
Baton Rouge, Louisiana
Age: 35
Go-to drink order: Pepsi
No. 1 item on bucket list: Go to every single Disney park in the world
Favorite candy: A Snickers egg
What do you love about insurance?
You have knowledge about something that everyone needs to have, but something most people don't understand. You're able to explain things. You protect people's livelihoods. I also love that insurance is ever-changing. There's always something new to learn, there's always a challenge. It's super exciting for me.
Mentorship as chair-elect of the state young agent committee?
I am very excited about stepping into a mentorship role with the Independent Insurance Agents & Brokers of Louisiana Young Agents Committee (IIABL YAC). We have a lot of new people on our committee, and a lot of them are young women. We just had our IIABL board meeting, and two of the gentlemen who are on the state board have daughters coming into their agencies. They both asked about someone mentoring them, and I volunteered. I'm looking forward to meeting with them.
Biggest market challenges?
In Louisiana, it's hard to get the message out to consumers that agents are not the ones increasing their premiums by 50%. We're the people talking to customers, getting the phone calls. But we need our legislators to listen to us. We need our government to not be run by trial lawyers. A lot of it is consumer education because tensions and emotions are high. The Big “I" has been super helpful with the Hard Market Toolkit that provides resources to educate the public about what's going on, and IIABL has done such a great job of giving us tools to keep customers informed.
Tyler Ross
Agent
Portland, Oregon
Age: 32
Go-to drink order: Champagne
No. 1 item on bucket list: Watch a baseball game in Fenway Park
Favorite candy: Snickers
How did you get started in insurance?
I had just graduated college, just got engaged, and my fiancée had been working at an insurance agency. Her boss was our marriage counselor, and after a session, he told me that I'd be good at insurance. I had no clue what I was going to do out of college, so I was like, “Sure, sounds great!" Many years later, I'm still in it.
Millennial and Gen Z stereotypes?
I think millennials have a stereotype of taking the easy way out, just wanting to work from home or do the bare minimum. But our ability to multitask is a huge advantage. In terms of how we work, we're willing to change processes and make things easier and more seamless. I also think there's a better understanding of work-life balance with millennials and Gen Zers. Speaking as a father of two boys, I see more parents prioritizing being around their kids, taking them to school, going to activities and just being around. I think that's on the rise and that's super healthy.
Work-life balance?
I coach high school baseball in the spring, and that's almost a full-time job in itself. I'm also married and have two kids, a four-year-old and a four-month-old. In a commission-based business, you can burn out quickly. Having a hobby, like coaching baseball, keeps the burnout away.
There's a place now for people in the workplace who want to spend more time with their family versus pounding the pavement to get as much money as possible. We have more room for healthier work-life balance in a lot of different stages, including people who say, “I love my work, and I'm going to do my best, but I also care about other things outside of work."
Kasia Anderson
Vice President, Business Insurance
Eden Prairie, Minnesota
Age: 30
Go-to drink order: Hot water with lemon or Sauvignon Blanc
No. 1 item on bucket list: Visit all Seven Wonders of the World
Favorite candy: Not a candy person, but I can devour chips and dip any day of the week
How did you get started in insurance?
My dad is an insurance agent. When I was a kid in Girl Scouts, he made me go around and ask each individual person in the office if they wanted to order cookies. That's where my salesperson mentality started. When I joined the agency after college, all the people I had been selling Girl Scout cookies to since kindergarten ended up being my coworkers.
Goals for your term as president of Big I Minnesota Emerging Leaders?
I want to encourage more participation from other emerging leaders throughout Minnesota to provide opportunities to network and learn from experts in the industry.
Another objective is helping other women in this industry explore their opportunities and continue to build on their strengths. Traditionally, there are more women in service roles within their agencies and my objective is encouraging women to explore all roles, such as marketing, sales and leadership.
Encouraging more women to branch out in insurance?
I'd like to encourage a new wave of hybrid roles for women—whether it's trying out being a part-time agent or experimenting with another role. When entering the insurance world as a female producer, there were only two other female producers in the agency, and I want to help encourage other females to explore this avenue.
I want all agents to test the waters and get creative in embracing the hybrid opportunities this industry offers, because you never know until you try.
Weston DeFrisco
Sales Enablement Manager
San Luis Obispo, California
Age: 32
Go-to drink order: Diet Coke
No. 1 item on bucket list: Take six weeks off work and travel to the South Pacific
Favorite candy: Trader Joe's frozen mango cream bars
Best thing about being an independent agent?
It allows us to be true advisers and bring the best options to the table. Being an independent agent allows you to serve your clients in a more meaningful way because you're able to shop and put together a portfolio of coverage that truly fits their needs versus being boxed into one carrier.
Role with your state association?
I'm on the Independent Insurance Agents & Brokers of California (IIABCal) Independent Insurance Producer Service Corporation (IIPSC) board of directors. The IIPSC board develops programs and products for IIABCal members. It involves a lot of creative thinking as independent agents come together to think about products that could serve independent agents in the state. It involves looking for gaps in what's not currently available or needs to be improved. There's been a lot of great, creative brainstorming in those board meetings. It's nice to be in a room with people who are all focused on bettering our industry and expanding product availability to fix the insurance problems that we're having in our state.
Role model or mentor?
Our CEO, Brendan Morris. Ever since I started working here in 2014, he's been an amazing mentor to me. He truly cares about his clients and community involvement, and has a continued focus on the perpetuation of our agency and staying independent. I respect it a lot, and I am truly bought into the vision of what our firm is trying to build.
Jesica Hernandez
Commercial Lines Producer
Winston-Salem, North Carolina
Age: 26
Go-to drink order: Aperol spritz
No. 1 item on bucket list: Travel to Italy
Favorite candy: Airheads
How did you get started in insurance?
When I was 17, after working at Subway for two years, I found myself at a crossroads contemplating a return to education or the pursuit of a long-term career. My cousin works at Alliance Insurance and encouraged me to apply for a vacancy. I was hired the same day I interviewed and started a few days before my 18th birthday.
The following June, I earned my property & casualty license. The class was quite different from what I dealt with at work and the questions clients asked, so it was helpful that I was already working in an agency while studying for it. I'm not sure I would have passed the test the first time without that experience.
What do you love about insurance?
We're always learning something new. I specialize in commercial insurance, where the unique nature of each business necessitates ongoing adaption and learning. One thing I've always loved, even outside of work, is helping other people. The opportunity to help people protect what they've worked hard for is very fulfilling.
Goals for the future?
I've been at Alliance for nearly nine years, primarily working in service with some quoting and selling every so often. As of March, I officially transferred to a producer role, making a significant milestone in my career. I'm excited to grow my book of business and aspire to be as successful as our top-performing producers.
Cole Schanandore
Agent
Conway, Arkansas
Age: 31
Go-to drink order: Black coffee
No. 1 item on bucket list: Fly fishing in Alaska
Favorite candy: Reese's peanut butter cups
How did you get started in insurance?
I went to the University of Central Arkansas, which is in Conway where I grew up. I took an introductory class in risk management and insurance and really enjoyed it, so I ended up majoring in insurance and risk management. As soon as I graduated, I worked as an underwriter. After a few years, I made the jump to the agency side. As I understood the business more, I found the commercial side to be interesting. I appreciate the freedom of sales, and I like the thought that the harder you work, the more successful you're going to be.
What are some of the biggest challenges the industry is facing?
The industry is facing a hard market. It seems like new rules and underwriting changes are coming out fast. In Arkansas, companies have pulled out of the state and a few have gone into liquidation. Consumers need actual insurance advisers now more than ever before.
Pros and cons of multiple generations in the workplace?
The insurance industry is becoming increasingly technology-driven. Millennials and Gen Z have been raised with technology, so some changes are second nature to us, while it might be harder for more established generations to adapt to some of the technology changes. On the other hand, the relationship and personal touch aspect comes easier to Gen X and older. We're still in a relationship business—we're just trying to merge technology with it. At the end of the day, I think different perspectives are important in any organization. Every generation needs to be adaptable and learn to work together as a team.
AnneMarie McPherson Spears is IA news editor.
