Young, Competitive, and Winning in Commercial Insurance | Livy Rayfield

Think insurance is just paperwork and premiums? We pull back the curtain with Livy, a finance grad who found her stride helping contractors grow through smarter risk and bonding. From graduating early to choosing a privately held firm over a public giant, she walks us through the moments that changed her view of sales and why this niche is a best‑kept career secret.

We get candid about the first 90 days: the pressure, the rejection, and why running a proven playbook beats reinventing the wheel. Livy explains how coachability and interpersonal trust fuel results, and how IGA’s leaders “get in the ditch” with new producers—modeling calls, debriefing losses, and accelerating the learning curve. Cold calling gets a reality check, too. When contractors need coverage and bonding to win work, outreach becomes service, not spam. The scripts are scaffolding for discovery, not theater, and hit rates rise with competence.

Livy also shares what it’s like to thrive as a young woman in a male‑dominated space. Competence earns respect, but presence and listening open real conversations—about cash flow, backlogs, WIP, bonding capacity, and safety—so you can fix root problems and help owners win jobs. We explore resilience as a daily practice: treat no as information, move with abundance, and spend time where you can truly help. For high‑achieving students or career changers drawn to income upside, autonomy, and impact, her advice is simple: take the grit assessment and be ready to trust the process.

If this story sparks something, follow the show, share it with a friend, and leave a quick review—then check out opportunities at IGA to see if your grit matches our playbook.

Learn more at www.igagrit.biz.

Transcript

Meet Libby And Early Impressions

SPEAKER_01 1:37

Welcome to the Grit Factor Podcast. I'm Drew Powell, and here we explore what it takes to succeed through the lens of guts, resilience, integrity, and tenacity. These are the values that drive high-performing leaders and shape the culture at the Insurance Group of America. Each episode we'll sit down with industry trailblazers, IGA team members, and inspiring professionals who have embraced grit to overcome challenges, seize opportunities, and create meaningful impact. Whether you're considered joining IGA or simply looking for the tools to take your career to the next level, you're in the right place. So buckle up. It's time to discover the grit factor. Libby, welcome to the podcast.

SPEAKER_00 2:21

Well, thanks for having me.

SPEAKER_01 2:23

We've got Zach and Booy in the background heckling us. They're the peanut gallery. So if you hear voices from the back, that's that's they're on your team, they're cheering you on. But glad you're here. Glad you're willing to talk about your experience at IGA. How long have you been a part of the company now, remind me?

SPEAKER_00 2:39

So I started in April, so about eight or nine months.

unknown 2:43

Yeah.

SPEAKER_01 2:43

Gosh, it feels like you've I'm new. I'm newer than you, but I feel like you've been here like forever. It's like one of those things where I'm like, oh, Livvy's just been here for a long time, but you're killing it.

SPEAKER_00 2:51

It really does. I feel like I've been here for forever, too. I mean, the relationships that I've built just within this company are so strong that I feel like I've known all of my co-workers and bosses and everything for so long.

College Path And First Sales Steps

SPEAKER_01 3:07

Yeah, that's awesome. Well, take us back. I want to hear a little bit of your story and just kind of your your college experience and kind of how you got into this, into this. So, what what were you planning on doing in your life? What were you studying in college? Like, how did you get to this point?

SPEAKER_00 3:20

Yeah, so like most 21-year-olds, I I graduated college at 21, and I really didn't know exactly what I wanted to do. Um, I went to MTSU, so Middle Tennessee State University, and I graduated a semester early with a degree in finance, and I always kind of knew I wanted to go into a sales role. Um I just didn't know exactly what I wanted to sell, and I did an internship at Brown and Brown Insurance, which is a big publicly traded firm, and I kind of got a surface level understanding of the insurance world and kind of how that works, and that was very intriguing. Um, but I also went into real estate while I was in college, got my license, sold a few houses, and um, you know, I just I knew I had good skill sets that would complement sales, and I knew the opportunity that that the sales world could provide. I just wasn't sure exactly what I wanted to sell, right? And and everything.

Internships And IGA Opportunity

SPEAKER_01 4:30

So Yeah, that's interesting. How so how did I GA get on your radar?

SPEAKER_00 4:34

Yeah, so kind of just through um my insurance professor in in college got me connected with Jamie. I took the grit test, I did an interview with him, and then I actually ended up working at Brown and Brown Insurance. Um, and then I was able to see kind of how a publicly traded firm operates. And then of course IGA is privately held. So then I kind of got reconnected after that internship and after I finished college with Jamie, and he explained the opportunity, which I was able to understand a lot better after my experience at Brown and Brown and and sales with real estate. And um, I was like, wow, there's some real opportunity here. I'm just gonna give it a shot.

SPEAKER_01 5:19

Yeah, I love that. I love it.

SPEAKER_00 5:21

And I didn't it was great.

SPEAKER_01 5:22

So be honest with me, what assumptions did you have about insurance before you stepped into this world?

SPEAKER_00 5:29

Yeah, so I mean, I definitely never would have pictured myself if you would have told me at 18 years old I was gonna go into insurance or or construction, right?

SPEAKER_01 5:41

Right.

SPEAKER_00 5:42

I would have been like, you have you lost your mind? Like construction, right? This little blonde girl, no. Right. Um, but um, yeah, I thought it was just boring. I was like insurance, and then definitely construction. I just I was it's so male-dominated, I didn't even really think about having a role in it. But here I am.

First 90 Days And Rejection

SPEAKER_01 6:04

Well, I want to I want to get into that a little bit more uh a little bit later because I do think that's an important part for those that are listening or watching right now. The fact that you're a woman in this world, and then also just the the challenges you have, but you've actually turned those and use them as advantages for you in this role. So I want people to hear that and see like, hey, don't count yourself out just because you think insurance, construction, there's no way. I love that you that wasn't on your radar at all, and now here you are thriving in this role. So talk talk us through your first like 90 days. You get reintroduced with IGA, you're getting kind of thrown into the deep in the pool. Your first 90 days, what was the what was the hardest part or the most challenging part of your first three months here?

SPEAKER_00 6:43

I think just getting kind of the hang of everything. You know, we are trained very, very well, and we have a roadmap and a proven process that works. Yeah. And so just sticking to that process. Don't do any more, don't do any less, just stick to that process and just getting the hang of everything. And, you know, because it is hard. You do you do deal with a lot of um pressure and rejection, especially in the beginning. And so you just have to have resilience and kind of get through that that hump.

Grit, Coaching, And Trusting The Playbook

SPEAKER_01 7:18

Yep. Yep. Well, you you're kind of hitting on a little bit of of and this this is a cheat code here, but you know, one thing we look for in people in this role is that interpersonal trust, which we were talking before we started recording with uh Zach and Bowie. Just like it's hard sometimes to find the people that have the resilience part, the intensity, like you said, the ability to take rejection, but also at the same time be humble enough to receive coaching and to work the play. Like you said, it like for those that'll come in and just work our playbook, they're gonna be successful. But there's people, and honestly, like me, it's why I didn't pass the test that want to recreate the wheel all the time. Yeah. And that just isn't that doesn't it's not successful in this role. So you being high on resilience, high on intensity, but also you've got high interpersonal trust. Can you just talk a little bit about how those things come together for you to be successful in this role?

SPEAKER_00 8:09

Yeah. So like I said, it kind of just hits back on to the the point I made. There's a proven process that works here. Yeah. And so you just have to stick to it because they are a lot our sales trainers. Yep. And and Jamie is a lot older and wiser than you.

SPEAKER_01 8:31

And so um he's gonna take offense that you just called him old.

SPEAKER_00 8:35

I'm sorry. Um, and so you just have to trust the process, and and that's where the interpersonal trust really comes into play. Like, you know, you are gonna have rejection and you are gonna have high pressure and you are gonna have to have resilience, but you have to trust the process and keep going. And because it is a roadmap to success, truly.

SPEAKER_01 8:57

That's right. And our our leadership here has done a lot of hard work in looking at the data and looking at even, you know, I get to talk to a lot of potential candidates, and candidly, not very many pass through the the grid assessment, and that's because they've done so much work on really finding like who's gonna be successful in this role and who's gonna actually work. And then when they do find someone, you know, and and I'd love to hear your take on this, but it seems like once they find someone who fits that profile, then it's like we go all in. Like we're gonna really invest in this person and and help set them up to win and succeed. Has that been your experience?

SPEAKER_00 9:34

Oh, absolutely. They will get in the ditch and do whatever it takes to help you succeed.

Investment In Talent At IGA

SPEAKER_01 9:41

Yeah, I love that. I love that about the company. All right, I gotta ask you about this because I like I said, I get to have conversations with a lot of candidates, and one thing that comes up a lot is the elephant in the room of cold calling. Okay. And so I want you to just talk through like your experience on that. What is that actually like? How did you push through it? How is that different for for some people who are like, listen, I love the business side, I love the analytics, I want to get in, I love the finance side, I'm a finance major, but I'm scared about the cold calling part. I'm not know if I want to do the sales. Tell me your experience on that. How what is that the actual like day-to-day of that in this role?

SPEAKER_00 10:18

Yeah, so that's a great question. Um, cold calling can be you know intimidating to a lot of people, and it it honestly scares people away from you know, a job in sales.

SPEAKER_01 10:31

Right.

Cold Calling Myths And Reality

SPEAKER_00 10:32

But with this job in particular, it's so hyper focused. The people that we are calling need our help. Honestly, some of them desperately need our help.

SPEAKER_01 10:46

They're grateful you're calling.

SPEAKER_00 10:47

So once you get your scripts down and the training down and your understanding of bonding and and you know insurance, and you know kind of what you're talking about, yeah. Um, you start seeing those hit ratios because these people truly need right our help. So it doesn't necessarily feel like a cold call, even though technically, yeah, it is a cold call, but it really just doesn't feel like that. It's very much different than your typical cold call.

SPEAKER_01 11:20

Well, and it's it's why we feel like this industry is one of the best kept secrets, is because the the companies we get to partner with, like you said, they're actually required by law to have what we're offering. So, like you said, when you're calling them, it's not like you're trying to sell them something they don't need. Right. We're actually helping improve their business. And when you guys get to build your book of business with these companies, you know, we we like to think of ourselves as as one of their most important external partners because we are literally getting in and helping them grow their business, grow their company. Could you have any examples that come to mind of of people that you're working with and just kind of like what's some of the work that you're doing with them that is rewarding for you where you're like, man, I get to actually come in and help this this company grow?

Serving Contractors As Business Partners

SPEAKER_00 12:03

Yeah, no, it's all it's all the time.

SPEAKER_01 12:05

Yeah.

SPEAKER_00 12:06

Um, so these companies, you know, there's there's tons of examples, but you're right, we do work as external business partners, um, not just as insurance agents by protecting their business or bonding agents by helping them get these jobs, but even we get them connected with construction CPAs, you know, contract CFOs. Yeah. Um, so there's there's so many different avenues where we work as a business external business partner, essentially.

Women Thriving In A Male Space

SPEAKER_01 12:36

Yeah, I love that. All right, I want to pivot for a second, and you mentioned this earlier, and I don't I want to go there. I want to talk about working as a woman in this space because it is, as you said, pretty male dominated. Um, so I'm curious, um, what has your been your experience been like just stepping into this role as a young woman?

SPEAKER_00 12:56

Yeah, so so there is a certain level as you know, a young blonde girl walking in talking about construction. Um but at the end of the day, if you're able to walk in and and communicate, articulate, and differentiate yourself to these business owners, then it doesn't matter, you know, if you're a girl, boy, you know, whatever the case is, if you're able to do those things and you can help them, right, then you'll be successful.

SPEAKER_01 13:40

Yeah, I love that. And like I mentioned earlier, you've you've actually turned it into an advantage. So w what do you think, if if any, what do you think the advantages are that a woman could bring to this role that maybe don't get talked about enough?

Turning Differences Into Advantages

SPEAKER_00 13:53

Yeah, um, honestly, I think that as a woman, um like when I'm talking to these business owners, I feel like there's um a sense of like they're able to kind of just like break down and like and explain their problems. They they feel more comfortable. I think you know, girls just naturally and women just naturally have more of a caretaker. Um you know, do you know what I'm trying to say?

SPEAKER_01 14:23

Absolutely. I feel I feel like the being more receptive. Right. I think sometimes in the room, when guys come in, not always, but there can be a competitive alpha male, whatever. But I know when when a strong, powerful woman comes to the room that's competent, um, you know, it can diffuse the situation. It can help open up to where you don't feel that competitive streak or whatever. And you've set a great example of how to like use that to your advantage, where they come in and immediately because of your competency, they respect you, but they're also their guard is down and they're able to listen and receive and all that kind of stuff. And I think that's that's part of your success. Wouldn't you say? I mean, I'm I don't want to put words in your mouth.

SPEAKER_00 15:02

No, you said it better than I did. Yeah, they're just they can be more in in certain scenarios, they could be more receptive for sure.

Resilience And Handling No

SPEAKER_01 15:08

Yep. All right. So you've been doing really well early on. What do you think would separate you and the others on the team who are succeeding um from those who who might struggle?

SPEAKER_00 15:20

Um, I think just resilience at the end of the day, you know, not letting rejection set you back and being able to get back up because you will have have times where you you are in spots where you're like struggling. Yeah. Um, you know, and and you just have to get back up. You have to be resilient, you have to have grit. Yeah. And so if you if you're not coachable and competitive and gritty, then you're gonna struggle.

SPEAKER_01 15:50

Yeah. Is that just does that come naturally for you, or like how do you handle rejection without letting it like completely crush your confidence? Well, I don't know that I would do so well. I'd take it real personal, but it seems like for you you're able to just kind of like let it roll off your back and like on to the next.

SPEAKER_00 16:08

Is that is that something you is that a learned behavior or um I think honestly, some of it does come naturally, but um, I mean, you just can't take it personally. You just gotta be resilient and just keep going. I mean, on to the next. There's honestly, at the end of the day in this industry, there are so many people that need your help. If they don't want to take your help, yeah. I mean, I kind of look at it like it's your loss.

SPEAKER_01 16:38

Yeah, no, that's true.

Matching Solutions To Real Needs

SPEAKER_00 16:39

And maybe that's not exactly how you should look at it. I don't know, but that kind of helps me get through it. I'm like, look, I'm trying to help you. That's I've done all I can do. If you're not willing to accept that, then roll on. I gotta spend my time somewhere else with somebody that you know somebody else needs my help.

Advice To High-Achieving Seniors

SPEAKER_01 16:55

That's so true. We don't have to have a scarcity mindset around who we can help and who we can serve. And I think it's why going back to the sales conversation, I think it's why it becomes easier to sell because, like you said earlier, this is helping solve a problem for them. Like it's a real need. Now, if they don't have the problem, they don't have a need, then we'll on to the next person who does. But when you get matched with that person, I mean, you're you're really solving major problems for their business. I love the stories of people who have come back around and said, Man, we wouldn't be where we are today in our business if it wasn't for how you helped us get there. And that's the stuff that's so rewarding. Oh, yeah, we feed off that stuff for sure. All right. Last question for you, unless you've got anything else you want to say. This has been awesome, super helpful. Um, what would you say to someone who maybe is like a high achieving college senior who wants this income potential, the autonomy and the growth, and is just unsure if this might be the right, right path for them?

SPEAKER_00 17:54

Well, I would say the first step is to just take the grit test. Um take the test and see if see if we're a good fit and and just just take that first step.

Closing And How To Learn More

SPEAKER_01 18:07

Yeah. And I tell people all the time that assessment is there really to serve them as much as us because we don't want anyone getting into this role that, you know, three months down the road or however long they've realized this isn't for me. So that assessment really does serve them for them to know, hey, if this is a a spot they want to be. Right. Well, Libby, thanks for jumping on. Guys that are in the room, any other questions, any comments from the peanut gallery? You guys have been quiet. I thought you'd be heckling us a little bit more. Oh, she did great. You guys are a great team. Yeah, awesome.

SPEAKER_00 18:37

Thanks, brother.

SPEAKER_01 18:41

Well, thanks for joining us on the Grit Factor Podcast. We hope you're leaving inspired, equipped, and ready to embrace the grit values in your own life and career. If you enjoyed today's episode, be sure to subscribe, leave us a review, and share it with someone who's ready to level up their leadership. And if you're interested in learning more about the culture and opportunities at the Insurance Group of America, visit us at Iga.vis forward slash careers. Remember, success isn't about avoiding challenges, it's about facing them with grit. Until next time, stay bold, stay resilient, and keep pursuing excellence.