As a teenager, Tyrone Jordan II earned the opportunity to fulfill a lifelong dream: playing football at the University of Michigan.
But during his junior year of college, when he realized he wasn’t headed to the NFL, Jordan’s goals changed. He teamed up with his father, who was with a large automotive company at the time, to start a company in business development and strategic planning for international suppliers.
Because of his father’s busy schedule, Jordan took on the role of CEO at the young age of 19-20. “I was doing these meetings, flying to Germany and Brazil—it gave me business experience that normal 20-year-olds don’t get,” says Jordan, 33.
When the automotive market went south in 2008, “we wanted to supplement our consulting fees, because a lot of the people we worked with had stopped producing for a while,” recalls Jordan, who says he “happened upon insurance” through retirement services, then group benefits, and then an agency that focused primarily on the public sector.
Today, Jordan is celebrating five years with Kapnick Insurance Group, a large family-owned agency based in his home state. “I’ve had plenty of other opportunities—I have a pretty large network, coming from the University Michigan and playing college football,” he points out. “But I love the insurance industry. The work I do for my clients and the joy I see out of them when we find a solution—that is extremely rewarding beyond the commission checks.”
Every day, millennial insurance agents like Jordan are finding plenty to love about insurance. What brought them here? What makes them tick? And why are they sticking around? Learn what 10 millennials have to say about where the industry is headed—and how they fit into it.
Vice President, Client Executive, Education & Public Entity Specialist
Kapnick Insurance Group
Ann Arbor, Michigan
Age: 33
Guilty pleasure TV show: ”Billions”
In your earbuds: The new Khalid album on repeat.
The app you can’t live without: Nike SNKRS app (I’m a big sneaker collector—I have 300+ personal pairs).
Work/life balance?
When I was growing up, my dad always stressed to me that there’s career time and there’s family time, but time in general is our most valuable asset. I live in Chicago, but my office is in Ann Arbor, so I’m doing the whole millennial remote work thing.
It works out really well because I get to be home with my family. I have a 10-month-old daughter, and my wife and I own a gym in Chicago—she started it a year before we met six years ago, and then we expanded it twice together.
When my wife and I first got married, we decided as a family that the gym was going to be something we were going to continue to grow. If Kapnick hadn’t been so flexible about letting me work remotely, I was going to have to consider something else, because I didn’t want to spend that much time away from my family.
The role of technology?
I don’t necessarily need to be face to face. Between Go-To meetings and Skype meetings, clients are really receptive to communicating via modern technology. People are comfortable texting, emailing, hopping on Facetime—whatever it may be. It’s crazy how I can get a prospect to respond to a text message faster than I can an email.
Role model?
My father. I’ve never seen anybody work harder than what he had to overcome. Both of his parents were deceased by the time he was 12, so he raised my family members, started off at GM as a security guard and ended up retiring as president of an automotive company. He went and got an executive MBA in aerospace at 53 years old. He’s always been my guidance if I’m having a tough time. He’s always the first call I make.
Commercial Account Executive
Briggs Agency, Inc.
Merrillville, Indiana
Age: 25
Guilty pleasure TV show: “Friends”
In your earbuds: A variety of podcasts and music
The app you can’t live without: Maps
Why insurance?
My great-grandfather started our agency in 1946, and then in the early ’80s, my dad joined the agency. I didn’t have any plans to be in insurance when I was younger, but I took one of those career tests when I was in high school, and one suggestion that came up was a claims adjuster.
My dad used to be a claims adjuster before he joined the agency—he lived in Jamaica for four years, and I remember I did a project on some of the hurricanes he worked on. I thought that was kind of cool, so that’s how I got interested in the insurance business originally.
I’ve also always had a passion for the fire department. I went to school at Eastern Kentucky University and got a bachelor’s degree in fire protection administration, and they had an insurance program there as well. I took several property-casualty classes in their insurance department and really liked it.
I’ve been working here at the agency since I graduated about two years ago, but I also work part-time in the fire department locally.
Finding balance?
The fire department is a big commitment, but I love doing it. We have meetings once a week, along with regular training. We’re a small fire department, but we’re busy. I live real close to the fire station, so usually I’m right there whenever we get calls, even if it’s two o’clock in the morning. I’ve been involved for about five years now.
All of it ties in well with my insurance role. I understand building hazards, and I’m also very familiar with our local buildings and codes. The people I’ve met—firefighters, police officers, first responders—some of those connections have been helpful and useful as far as regular business goes, too. There’s a lot of trust there.
Advisor, Innovation Risk
JJ Wade & Associates
Davidson, North Carolina
Age: 33
Guilty pleasure TV show: “Below Deck” is pretty awful but addictive.
In your earbuds: “Hip Hop BBQ” playlist on Spotify—it’s appropriate for any situation.
Netflix or Hulu: Still loyal to Netflix, but Hulu’s trash TV selection is strong!
Why independent?
My breaking point with my captive agency was in 2016. I had formed a relationship with a decent-sized medical device manufacturing company, and I was told, “It’s outside of the appetite guidelines.” I had to find some greener grass.
My agency is very niche-focused. I work in three main verticals—technology, life sciences and manufacturing. We’re not a volume-based agency. We’re looking for a certain class of business, and we’ve positioned ourselves to capture that.
Perpetuation gap?
Changing the culture is important. We’re not Google or anything, but we can bring our dogs to work, I can wear shorts to the office—I can do my job the way I see fit. There isn’t a mold at our agency of how the agent should look or what the sales approach should be.
Figuring out a different sales cycle, one that empowers the person who’s actually facilitating the insurance purchasing process, is really important. I’ve been empowered to not just pull X dates and make 100 cold calls a week. We enrich our knowledge through strategic partnerships and associations in the industries we are targeting, and we figure out a way to relate to the industries we serve.
Everyone sees insurance as the guy in khaki pants sitting at a desk waiting for the phone to ring. That’s not the model anymore.
Advice for a fellow young agent?
Develop a niche based on your personal interests. If you want to be a generalist, that’s fine—a lot of people have made a lot of money writing construction and retail and mercantile and habitational.
But where I’ve found success, as someone who was ready to leave the insurance industry because I was doing the same thing over and over again, was to find challenging verticals where the risks don’t fit the box of typical insurance.
Vice President
Garriques, Lloyd & Mcmahon Insurance
Richmond, Virginia
Age: 34
Guilty pleasure TV show: “Outlander”
In your earbuds: A little bit of country and today’s hits
The app you can’t live without: Toss-up between Facebook and Instagram
Why insurance?
My granddad started our agency in the 1960s, and when he retired, my dad took it over. I did not have any interest in working in insurance—I went to college and majored in advertising, so it was my dream to do something in that industry. My dad did offer me a position when I graduated, but I turned it down. I wanted to pave my own path.
I enjoyed working in advertising, but it’s a tough career—lots of long hours. My dad eventually came to me again because I needed something with more personal connection. About eight years ago, I ended up coming here to work at the agency. It was the best choice I ever made.
Embracing change?
When I started here, my dad didn’t even have a website. We weren’t on social media, and we had the same logo from the 1960s from when my granddad started the agency.
Now, we have a new website for the second time. We rank on top in a Google search, we’re on social media, and we’re gaining more online leads because of all that. Staying on top of those things has really helped us grow.
Millennial stereotypes?
The two that bother me the most are that we’re lazy and we’re entitled—that everything’s just given to us. Growing up, my parents always instilled in me that if I want something, I have to work hard for it.
I graduated college when the economy was at its worst. It was very hard to find a job, but when my dad offered me a position, I turned him down. I could have had an easy-access job, but I ended up working several part-time jobs to make ends meet because I wanted to do my own thing. I’ve always had a very strong work ethic.
Director of Production
Downey Insurance Agency, Inc.
Marlborough, Massachusetts
Age: 30
Guilty pleasure TV show: “The Blacklist” and “The Office”
The app you can’t live without: Zillow
Spotify or Apple Music: YouTube
What’s to love?
For me, what’s exciting about insurance is sales. I’ve always worked as a producer, so I never had a salary—just straight commission. I have all the flexibility I want, but I’m paid based on performance, so the more I sell, the more I make.
Early on, not having any connections, it was hard. I always had two or three different jobs at the same time.
Work/life balance?
I have a wife and a three-year-old daughter, and we have another baby on the way. When my daughter was born, that’s when I decided to take the risk to leave my salaried position as the environmental manager at a nursing home and be a producer full-time.
If you think about it, it wasn’t very smart—my wife wasn’t going to work, and here I was leaving my salaried job. But I pretty much took a leap of faith. I wanted the flexibility to spend more time with my family.
Before I took that leap of faith, with insurance, it was like I had a faucet that was leaking a little bit of water at a time, here and there. But the minute I went full-time, it was like the faucet fully opened. Everything just came together with God ahead of it all. It was worth the risk. I now have great people around me, and they offer strong support. My dad, Natan Da Silva, is my assistant, and without his help, I would not be where I am today.
Competing in personal lines?
Personal auto is my strongest line. I have very good relationships with different dealers. I don’t pay for those leads at all—they just love us because we’re right on the ball. I’m writing on average 50 new policies a month. Last month I hit 65.
Director of Client Services
Soderberg Insurance Services, Inc.
Lynnfield, Massachusetts
Age: 27
Guilty pleasure TV show: “Gotham”
The app you can’t live without: Disney Now (it keeps my child sane in the car)
Spotify or Apple Music: Pandora
Your competitive advantage?
I speak four languages—English, Spanish, French and Portuguese. It’s great for customer service, because I may have a customer who speaks a little English, but they just feel more comfortable speaking in their own language. They feel more confident that they’re asking the right questions and that nothing’s falling through the cracks.
People don’t really get that around here. We have customers whose agencies are really far away from their house. They’ll say, “My agency is an hour away, but it’s the only one I could find where someone speaks Spanish. Can you help me out? I’d love being able to come closer to my home rather than having to drive an hour to get something simple done.”
Millennial stereotypes?
When I first started, I would meet clients who thought I was too young. When I talked to them on the phone or via email it was fine, but when I met them in person, I could see them hesitate—“Does she really know what she’s doing?” So I got that pushback at first, but then once I got to talk to them and explain, they started trusting me more. Next time, they’d ask for me by name.
Biggest career mistake?
Going through school with just a retail job and not getting any professional experience. When I talk to my younger siblings, I tell them, “Make sure you do your internships.” It worked out for me, but I don’t want them to feel the way I felt. I felt like I was a failure because I graduated, and all I had was a degree. That’s it—I didn’t have anything else.
There are so many kids who are graduating. It’s not just good grades anymore. You have to set yourself apart.
Personal Lines Producer
Williams, Turner & Mathis, Inc.
Tucker, Georgia
Age: 29
Guilty pleasure TV show: “Game of Thrones” and “The Office”
In your earbuds: Probably something by Macklemore
The app you can’t live without: Weather App
Why insurance?
My mom owns the agency, but for the first 27 years of my life, I refused. I did not want to do it. I tried it one time for about three months, back in 2013, and I just was like, “I’m not meant to be behind a desk—this is not me.”
So I pursued my passion, which is wilderness therapy. I was an expedition leader for children with autism, Asperger’s, ADD, ADHD—it was a lot of working with special needs kids, where we would go on a three-week canoe expedition or a three-week hiking expedition.
After doing that for a couple years, I decided, “You know what, it would be really cool if I didn’t have to sleep outside in a tent 300 days of the year. I’m tired of drinking coffee with bugs in it—I’m ready to live inside a house.” So I gave insurance another go.
I worked for State Farm in Texas because that’s where we were living—my wife was the assistant director at the camp where we met, so I worked for the enemy for a while just to learn. I discovered that, much to my dismay, I liked it.
Advice for a fellow young agent?
A career in insurance is kind of like when everyone’s saying, “Oh, wow, this is a really good show,” and you watch the first two episodes and you’re like, “Ehh, I don’t think it’s for me.” You have to at least get to episode five. It’s not right away that you’re going to be like, “Ah, this is it! I understand!”
You’ve got to get through the licensing and learning, but once you’re able to kind of do it on your own and you get your footing, it’s really fun. It’s just not instant gratification. Give it a little time.
Account Executive
HN Insurance Services
Alpharetta, Georgia
Your age: 36
Guilty pleasure TV show: “The Chi” and “Big Little Lies”
The app you can’t live without: iPhone email app
Spotify or Apple Music: Apple Music
What’s to love?
I was an underwriter for almost eight years, so the drive for me is when I educate someone about something they didn’t know before—when I get to teach a continuing education course or speak at a meeting. That’s what I get my high from the most—seeing that lightbulb go off, where someone goes, “Oh! I hadn’t considered that.”
Perpetuation gap?
The perception of insurance agents just knocking on your door and being aggressive—that image has stayed, and unfortunately, it’s the older man in the tie. In order for us to continue, we have to push diversity in all forms. We have to get more women in higher positions, underwriting positions, agency ownership positions, and we have to attract minorities into the industry.
As a country, our demographic composition is changing. We have to read the landscape and realize we have this diverse pool of potential clients and talent—let’s go out and get qualified people who can fill those roles. That will not only allow for that perpetuation to continue, but also allow us to reach clients we never would have considered reaching.
Making it happen?
The focus needs to be on leadership positions, because that’s where the grand-scope vision changes are made. You need somebody in the C-Suite who can say, “Hey, maybe we can present this this way,” or, “Have we ever considered X?”
You can hire a bunch of people of color for lower- or mid-level management roles, but if everybody at the very top is of one particular gender, culture, background or race, you’re not going to create an environment where people can feel confident and comfortable sharing diverse views at all levels. You have to allow different perspectives to come into play. It has to be intentional.
Customer Service and Business Development Specialist
Wilson and Company Insurance Services, Inc.
San Diego
Age: 27
Guilty pleasure TV show: “Grey’s Anatomy” and “Jeopardy!”
In your earbuds: Usually a podcast (NPR or “Armchair Expert”), or the “Roots Revival” playlist on Spotify
The app you can’t live without: Instagram, Mint and NetCam (to spy on my dog)
Marketing secrets?
We totally steer away from the automatic posting programs offered by many carriers. We focus on what we do in the community or just little things around the office. It seems silly, but that helps make it a little bit more personal, because everyone’s seeing those same Don’t Text And Drive ads everywhere. If you see our faces, a picture of us saying, “Don’t text and drive”—you gain a deeper, more personal connection. Maybe you’ll pay attention rather than scrolling right past it.
Perpetuation gap?
It’s a great job—sure. But how do you tell 18-year-old Annie she should go into insurance? I wasn’t going to listen to my dad, I wasn’t going to listen to my grandpa, I wasn’t going to listen to my mom.
I think all the time about what to do to make it seem cool, but it’s just so ingrained in our heads—especially being a fourth-generation agent and picturing my dad, my grandpa, my great-grandpa, going to work in a suit and tie, meeting for lunch.
That’s not what we care about as a generation. We have so many ideas, and they may seem crazy and absurd and impossible, but we know what our generation wants. Whether we’re trying to write these cool funky commercial accounts or just a ton of renters insurance because our peers can’t afford to own, the higher-ups in the industry need to appreciate what we bring to the table.
Biggest career mistake?
At the beginning, I was making a mistake all the time. But hopefully, I’m never going to make those mistakes again, because yeah, I had to call the territory manager at 7 p.m. on a Friday because I messed up in a big, big way. I figured it out. That’s how you learn.
Account Executive
Copple Insurance Agency
Lincoln, Nebraska
Age: 25
In your earbuds: Foster the People, Breakbot, Private Island, OneRepublic
Spotify or Apple Music: Neither (I download all my music—maybe I’m older than I thought)
Netflix or Hulu: Both, but I use Netflix more. No cable, though!
Millennial stereotypes?
One of the things they peg us with is being too needy—needing constant validation. What I see is that I like to get some feedback on the status of my work. “Hey, did I do this right? Is there something I can improve on?” Just communicate with me a little bit, and with a little extra direction, I’ll do a better job next time.
I think that’s a generational difference. With the older generations, it seems like “no news is good news.”
Biggest career mistake?
During that first year or two, you’re out there trying to produce business, and you’ll take pretty much anything that comes through. I wasted so much time “practice-quoting” for accounts that I was never going to get, and it’s because I didn’t know the right questions to ask.
Over this past year, I’ve developed a system where I don’t really talk insurance during a first interaction with a prospect. I talk about all the tangentials—where you’re at, where you’re going, what you need, why you’re even talking to me.
It’s freed up a lot of time, and when I do have somebody that passes that test, I have a pretty high success ratio with writing their business. If only I would have had the courage to walk away in those early days, but you live and you learn.
Advice for fellow young agents?
Put people first. When you are in a sales profession and especially the insurance sales profession, everything comes down to your reputation and your integrity. Large or small, word’s going to get around if you’re not doing your job right—if you’re not acting ethically. There’s nothing more important than protecting your reputation and sticking to your convictions, even if it means losing a sale.
Jacquelyn Connelly is IA senior editor.
