From Classroom to Clients: Teachers Pivoting to Insurance

It’s been nearly five years since Leader's Edge began the Falling Into It podcast.

Our purpose is to interview up-and-coming insurance talent to find out why they chose this industry. These professionals have pivoted to insurance from careers on the fields of Major League Baseball and sailing the seas for the U.S. Coast Guard, to name just two.

In this episode, we’re going back to school. We meet two former teachers who went from education to employee benefits. First up is Casey Allsbrooks, an elementary school teacher and librarian for 29 years who recently jumped to working as an account manager at the Marsh McLennan Agency. Next, we meet Julia Lacoste, who taught middle school for two years before pivoting to insurance, where she works as an account manager at CBIZ.

Both women share why they moved to the industry of risk. Their stories are a part of a larger narrative insurers may want to pay attention to: past educators being a great source of talent for the industry.

Read the Transcript 

Disclaimer: Podcast transcriptions are computer generated, please excuse errors. For the most accurate version of the conversation, please refer to audio. 

 
Casey Allsbrooks: And it’s also been a big shift going from being a leader in education where people turn to me to ask questions for answers because I’d been there for so long and then now I’m starting over almost like a rookie, and now I have to ask others for help.  

 
Julia Lacoste: Flexibility that this job is able to provide me is super nice. And it’s fun to solve client problems and to try something new. Nothing ever feels the same. And I think that’s something. Like I said, you don’t think about when you’re thinking of a dream job.  

 
Zach Ewell: Welcome to the Leaders Edge Podcast series Falling Into It this series shares stories and profiles from talent within the insurance industry. I’m Zach Ewell, content producer here at Leaders Edge. It’s been nearly five years since the series first began. The purpose of it to interview up and coming insurance talent to find out why they chose to work in this industry. The name of the series is reminiscent of the many stories I’ve heard of people who describe entering the insurance workforce by falling into it on accident or mistake. The hope of this podcast is that by interviewing new insurance professionals, we the industry can take these interviews, learn from them, and refine our outreach and marketing so that we can attract new talented individuals to work in the industry of risk. All while closing the talent gap.  

 
In the past, we’ve interviewed and learned from many individuals, from the fields of Major League Baseball to the seas where members of our US Coast Guard serve. Individuals with pasts such as these and more have shared their stories of pivoting careers to insurance. However, this episode of falling into it brings us back to school. We meet two past teachers who have both pivoted from careers in education to working in employee benefits. Casey Allsbrooks, a season pass teacher with 29 years of experience working in education teaching K through 4th grade, recently made the jump to working as an account manager at Marsh McLennan Agency. Secondly, we meet Julia Lacoste, who is still near the beginning of her career. She taught middle schoolers for two years before pivoting to insurance. Both women share why they decided to pivot to the industry of risk.  

 
Additionally, their stories are a part of a larger trend and link insurers may want to pay attention to past educators being a great source of talent to attract to their industry. We start our conversation with Casey’s background in history and education.  

 
Casey Allsbrooks: Well, I retired from the education field after doing it for 29 years and I spent 18 of those years teaching elementary school and I taught like grades. I taught K1, 2, 3 and 4 never got to the fifth grade. But about 15 years into my teaching career, I felt the desire to explore a different path but still stay in education. So I decided to get my master’s degree, pursue my master’s degree in library science so that I could be a librarian. So once I completed my degree, then I spent the last 11 years of my career as a librarian in the elementary schools and secondary schools. And as far as. Did I always want to be an educator or work in education when I grew up? Absolutely. Teaching was always my dream.  

 
I would always gather up my dolls and my friends, my sister and her friends, and teach them. And then they ended up. I. I joke now that they were the brightest kids on the block because they participated in. In all the endless lessons as I played the role of a teacher. And I was the kid that at the end of the school year when the teacher would pass out the leftover workbooks, or which I know those probably aren’t even in existence today, but she would pass out all the leftover workbooks. I would ask to take those home so that then I could play school with. With my friends. And then I very much enjoyed getting in my red pen and marking them up like I had seen my teachers do when I was young. You know, I didn’t think about content or anything.  

 
My teachers were a role model. And so I would watch them, you know, have command over the class, and they, you know, get to ride on the chalkboard, because chalkboards were in existence back then. Now we do whiteboards or not even Promethean boards now or whatever. So it was more of a role model thing and then I liked how, you know, she would. I remember specifically my teachers doing math lessons, and at the time, I was good at math, and so she would always do the, like, math races against somebody else on the chalkboard. And I just always wanted to be the one that got to do that as a teacher.  

 
And there’s something about the red pen that was very intriguing to me. I always wanted to grade papers. But as I got older, I became very passionate about reading and teaching reading and phonics and comprehension and fluency. So that was something that kind of drove me when it was time to go to college, that’s the path that I took, was to be able to teach reading.  

 
Zach Ewell: Similar to Casey, Julia also grew up with a passion of education. Her role models extended past teachers and her own mom, who is a teacher and later a principal.  

 
Julia Lacoste: I would say I have a pretty short history of working in education. I graduated college in 2021 and then I did a master’s program. And so I student taught for a year and I taught fourth grade. Then after that I moved across the country from Oregon to Charleston, South Carolina and taught sixth grade science. After that, which I’ll get into, is when I kind of made the switch to insurance and employee benefits. It was really only I’ve been in classrooms pretty much growing up and my whole life, my mom and family is in education, but definitely was a short history. And my mom was a teacher for her whole career and she’s been a principal in the education system for the last ten years or so.  

So like I said, I was always around it’s been in my family, but I just wanted to do something that I was super passionate about. Work with people was my main thing that I wanted to do. So I figured I was going to kind of do more of a service focused job. And then I kind of just switched into education. I took some education classes. It’s very service focused. You’re kind of working with kids across the board, families across the board. And I always loved school and just kind of thought I would switch my major to education. My mom told me not to. Which being in education, I think people get a lot. It’s obviously a very hard industry, especially right now. But I think in college, you know, I think you have to go through some of that yourself.  

 
And I think you don’t like 20 something year olds don’t like to take advice and have to learn a little bit on their own. I knew it was a tough career. I saw what my mom did, but I, I cared about it and wanted to be a benefit to society and all of those things. And not to say that what I’m doing now is not a benefit to society. It’s incredibly necessary. But you know, when you’re 21 and I had never been enrolled insurance myself, I did not even think of that. You’re not going to think about this career as helping others like you do with something like teaching. I guess it’s not as obvious.  

 
Zach Ewell: Next, both women discuss how they pivoted careers from teaching to insurance and what that pivot was like. As Julia mentioned, her mother was one of the reasons why she wanted to get into education. However, for Casey, it turns out her son was an influence in her joining the industry.  

 
Casey Allsbrooks: Okay, so I didn’t actively seek out a second career insurance. I knew that when I retired I wanted to do something to like supplement my retirement income. But my Son actually works in employee benefits, and he encouraged me to apply for an open position at his company. So I interviewed for the role, not at all expecting to get it, to get the job. But I was surprisingly hired despite having absolutely no insurance experience aside from a college job summer job where I worked in an auto insurance in the auto insurance industry. So when you ask if it was hard or not, transitioning to a new career at the age of 52 has been, it has presented its challenges. Most definitely because I’ve had to engage in extensive studying and so that I could expand my knowledge.  

 
I mean, yes, I’ve always had employee benefits because of my jobs, I would be offered employee benefits. So I kind of understood it, but I’ve had, I had to grasp it from looking at it like from an aerial view instead of just surface level. And so I also had to obtain my license for insurance. So I had to study for that. I had to pass that exam. But I did a pass first time and everybody was shocked. But so it’s been, and it’s also been a big shift going from being a leader in education where people turn to me to ask questions for answers because I’d been there for so long and then now I’m starting over almost like a rookie. And now I have to ask others for help.  

 
So that’s hard for me because I’ve been the one that always knew the answers. Now I’m having to ask for people to help me. But fortunately, I have a real, very supportive boss and very knowledgeable colleagues that understand where I’m coming from.  

 
Zach Ewell: And you said your son sold insurance or he worked insurance?  

 
Casey Allsbrooks: He works insurance. He works in employee benefits as well. And we work at the same company. Now.  

 
Zach Ewell: Guests, do you think attracted him to working insurance?  

 
Casey Allsbrooks: You know, I don’t know the answer to that question. He actually graduated from college with an education degree. And I kept telling him the whole time, I’m like, you know, education has been changing. I don’t think you want to go into that. But you know, I had to let him make his own decisions. And he taught for one year and he said, should have listened to you. He didn’t like it. He’s. And he said to me, he’s like, I don’t know how you’ve done this for as long as you’ve had as you have. And he and I actually were talking about this yesterday because he said, how did you stay in education that long? And I said, when I went to college, you got a degree.  

 
And that’s what you went to for your career, you didn’t get a degree in education so that you could go work in employee benefits. You went to school and got a degree in education so you could become a teacher. So I said, nowadays, as long as you have a degree, that seems appealing enough to a lot of companies, you know, that, hey, they’ve got a degree, they’ve got the study habits, they. They can do what it takes to get licensing done, that kind of thing. So he and I were talking about that, and he said that, you know, that’s a good point because he has a lot of friends who went into and got a college degree in something that they’re not even. It’s not even a related field to what they do now.  

So to answer that question, I’m sorry, kind of branched off that. No, he didn’t go looking for employee benefits either. He happened upon this job because a friend of a friend knew he was looking for something else. And kind of like I did. I mean, he. He introduced me just like someone introduced him to it.  

 
Zach Ewell: I was struck by what Casey said about generational change when it came to the attitudes and purpose of college degrees. Instead of a college degree just securing career longevity in a specific field, it could also be used to help pivot fields and career paths, something Casey’s son did and which Julia took advantage of early on in her career when her career mindset changed.  

 
Julia Lacoste: So I think my mindset just changed where I wasn’t scared to maybe take a career change. I had to deal with some hardships in schools, but it still was a really good experience. I just wanted to try something else. And I was like, I can always go back to teaching if it doesn’t work out. So I started applying to as many jobs as I could after the school year. Ended up just something business related. I wanted to do something completely different than in. Outside of education and something where I could use kind of like some project management skills. Organizational skills were some of my strengths. But at this point, I just had the mindset that I was willing to learn something new and I would figure it out.  

 
Zach Ewell 
Sure.  

 
Julia Lacoste: And I was like, if I don’t do this now, I don’t think I ever will. So it definitely was hard to learn new concepts. But like I said, I always loved school and I love learning, and this job is exactly that. I think insurance, there’s always something that you can learn about. I wasn’t going home and feeling like it was hard. I was more just excited to learn something new. The flexibility that this job is Able to provide me is super nice and it’s fun to solve client problems and to try something new. Nothing ever feels the same. And I think that’s something, like I said, you don’t think about when you’re kind of thinking of a dream job, but it really is different every day. So yeah, I don’t think this is something I ever would have gone into in college.  

 
But looking back, I’m incredibly happy that I did. For me, it’s being able to work my way up. Things are changing constantly as long you’re always a student in this industry. Flexibility. And then back to the part you said about the specific area of insurance.  

 
And why I chose that. Like I said, I kind of felt just fell into this job and applied and learned to love it as I got into it. I’m only about two years into this industry, so I can almost guarantee that I’m going to jump around to some different areas of insurance.  

 
Zach Ewell: After listening to both Casey and Julia’s answers, I was surprised by the similar reasons and themes for why they decided to both pivot careers to employee benefits. They both held strengths in learning new skills and expanding their knowledge. But what other strengths did they hold which made their pivot from education to.  

 
Julia Lacoste: Insurance work probably the biggest answer which I think can transfer to a lot of jobs, but would just be communication skills. I think it is incredibly useful in that I went from trying to teach, you know, 12 year olds photosynthesis, which can be incredibly hard when you have to bring content down to the level of developmentally a brain that is so many years behind your brain and make it make sense. I think teachers don’t get enough credit for that. But now it’s funny, a big part of my job is explaining benefits to employees and creating client deliverables to employees. And so I always think in a way it’s similar to teaching in that aspect. So I always think of myself at 21 and I knew nothing about insurance and I had to call my mom when I enrolled in benefits for the first time.  

 
And I was like, I don’t know what any of this means. And now basically I’m explaining benefits and a concept that I’ve spent two years studying to employees that they could just be starting their career. A lot of people, obviously they’re not going to know as much about it as the person working in the industry. And so just making it digestible and comprehendible to those people is very similar to teaching. And then I think like organization and task management and teaching, you’re handling a Million different things at one within a day. You’re constantly putting out problems, and the problems are going to be totally different. But I think just how I handle stress and how I can delegate tasks all applied to this role.  

 
Casey Allsbrooks: You know, diversity and inclusion is a huge thing. I always had to focus on promoting diversity and inclusion with students. You know, they come from all different walks of life. They all are different cultures, they’re all different learning styles. And employee benefits, I feel that’s kind of the same because I have to offer support for the different needs of employees and make sure that they’re getting what they need as far as the benefit package as a whole. And then this was one that I, I thought of policies. In education, there’s policies that you have to, you know, you have to. There’s certain regulations with the state, there’s certain regulations with educational standards. Just like there’s compliance in employee benefits, there’s labor laws. Yeah, that. I mean, I, I see a lot of comparisons there that I probably hadn’t.  

 
Wouldn’t have thought of had we not had this conversation. You know, in education, we teach that everybody makes mistakes. You know, you accept it and you learn from it. I have definitely had to follow that learning curve with employee benefits because I make mistakes and I have to learn from it. Communication skills is something else. You know, educators, as an educator, you all, you have to develop strong communication skills so that you can convey information in a way that students understand it, just as that skill is invaluable. And employee benefits, where clear communication about the benefits is essential, so they understand, you know, and this is something that I, as just an employee being offered benefits, see differently now. No one ever explained them to me like I want to explain to employees now.  

 
I just got a packet and, you know, were told to read it and pick what we wanted. Now, I am passionate about employees. Understanding empathy is huge. Working in education, you foster this deep sense of empathy and understanding of all the different needs. So it’s also crucial in employee benefits because it helps design programs that will cater to those varied needs of employees. You know, I wouldn’t be where I am without collaboration, teamwork, and employee benefits. Even as an educator. I mean, if you don’t have a team that you can rely on, that you can support each other in both sectors, then to grow, you don’t find yourself growing.  

 
Zach Ewell: Although there is no specific statistic that tracks the number of teachers who make a career pivot to insurance, there are many reasons, including those shared in this podcast, why past teachers make a great fit for future insurance talent. The industry of risk offers transferable skills, familiarity with customer service and collaboration, more flexible scheduling and opportunities for financial growth. Perhaps the insurance brokerage industry should focus more on this hard-working career demographic when recruiting talent and to end it.

Thanks for listening to this episode of Falling Into It. Find more episodes of this series at leadersedge.com or wherever you listen to podcasts.