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Taking Over: Meet Millennial Agent Annie Wilson

Like many other millennials, Annie Wilson is a jack of all trades. "I do mostly personal lines, but I also work on IT, social media, marketing," she says. "The insurance space is a great industry with so many different opportunities, which is super exciting."
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Annie Wilson

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)

Spotify or Apple Music: Spotify

Netflix or Hulu: Hulu

Why insurance?

I’m a fourth-generation agent. My great-grandpa started the agency in the ’50s-’60s, my grandpa eventually took over and then my dad took over.

I had always refused to ever think about insurance my whole life. I was like, “Absolutely not—it’s so boring, stale, pale and male, I don’t want to do this.” When I first started at the agency, I didn’t know anything. I couldn’t even tell you what my car insurance was before. It’s been a huge learning curve, but every day I learn something new. It’s never boring, which is the exact opposite of what I thought it was going to be.

I just had my two-year mark with the agency. We’re a really small agency, so I work with my mom and my dad, and we have one part-time commercial lines account manager who’s worked for my dad for about 25 years. A lot of our insureds were written by my grandpa, so we’re really focusing on reaching younger individuals either with renters insurance or homeowners policies if they’re purchasing condos around here. Our office is in a high-rise in downtown San Diego, so it’s exciting to be a part of that growth.

Embracing change?

I think as millennials, a lot of us have so many well-rounded skills. The insurance space is a great industry with so many different opportunities, which is super exciting. I think I bring an energy that is contagious to our office and the clients we serve.

I’m a jack of all trades—I do mostly personal lines, but I also work on IT, social media, marketing. Social media is huge when reaching out to different markets and potential clients to get that exposure through social media. When people Google us, we want to be right there at the top, and we want people to see our pictures, our faces, what we do.

Marketing secrets?

You hear a lot of different carriers say stuff like, “We have this six-week Don’t Text And Drive program, and you can just set up your Facebook and Instagram and Twitter to post automatically.” We totally steer away from that. Obviously I’ll repost and share things I think are cool, but we focus on either things we do in the community or just little things we do 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. But if you see our faces, a picture of us saying, “Don’t text and drive”—maybe you’ll pay attention rather than scrolling right past it.

Reaching the next-gen consumer?

The GEICOs and Lemonades of the world do such a great job targeting the younger generations, because we want things fast and quick. Millennials don’t necessarily want to chat face to face or talk to you on the phone forever. But you can text me a picture of your new car and we’ll text you an ID card right back, or you can contact us on social media and we’ll get right back to you. I’m on my phone all weekend—I’m never not working or aware of what’s going on. As independent agents, we really need to prove that.

Work/life balance?

That is something that has been huge for me—the fact that I can do a workout class or run and hike before work, that I don’t have to clock in at 8 and leave at 5. I can come in, make sure I get all my work done and then leave, or take a lunch break and the timing doesn’t necessarily matter. That’s is something you don’t really think about until you’ve had a job where you do have strict hours, and it’s huge for our generation. We don’t necessarily care about all the perks at work anymore. The flexibility is what we want.

Perpetuation gap?

Right now, this is the perfect job for me and my life. It has great work/life balance, and I’m able to help people and do so much in the community, which is what I care about most.

But there’s so much talk right now about how are we going to bring the young people in? What are we going to do to keep this industry alive and afloat? And I don’t know, honestly. I try and talk to people I know, because 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 was going to do the exact opposite of what everyone wanted me to do. 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 don’t feel like we have to necessarily do something for our whole life. We have so many ideas, and yeah, 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?

I have made a ton of mistakes. 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.

Jacquelyn Connelly is IA senior editor.

This interview is the ninth in a series that profiles 10 millennials in the independent insurance industry, based on IA’s July cover story.

Tuesday, June 2, 2020
Perpetuation & Valuation