Alicia Calhoun

I attribute my success to several defining influences, starting with the people who gave me my first chance in the insurance industry. Jim Watson ultimately hired me, but it was his office manager, Tammy Sherwin-Hanna, who first saw something in me and pushed for the interview to happen. She was the one who advocated for me when I had no experience, and without her belief, I never would have made it in the room.

Jim wasn’t the most polished person, he was a good old boy by every definition, but he believed in people. When he finally interviewed me, it meant running late for horse races in New Jersey, and that decision changed the course of my life. Jim taught me the importance of relationships, sales, and showing up consistently. Most importantly, he instilled a responsibility to give back. Throughout my career, I’ve tried to extend that same opportunity to others, because I know firsthand how powerful one person’s belief can be. I've reciprocated that same opportunity to others throughout my career because he taught me to always give back. Beyond that, my success comes from my background as an immigrant and the work ethic my parents instilled in me. I was born in Mexico City, and my parents brought my older brother and me to the United States when I was young. Both of my parents worked multiple jobs, and growing up, all I knew was work. Early on, I faced additional challenges. I was held back in second grade because I didn’t speak English, couldn’t read, and was diagnosed with dyslexia. Through a literacy program at my elementary school, I learned both English and how to read, an opportunity that changed the trajectory of my life and one for which I remain deeply grateful. Today, organizations like the Barbara Bush Literacy Foundation provide that same life‑changing support to thousands of children, opening doors and creating opportunities that make long‑term success possible. Throughout my 27 years in the industry, I've been a continuous learner. After getting my P&C license, I kept asking what's next and got my CIC, MLIS, CRIS, and CRM. I read a lot of industry content, pick up the phone to talk to underwriters about what's happening in the market, and stay hungry for knowledge. I have a passion for risk management and insurance, and I'm always looking for hazards and solutions. I also believe in betting on yourself and getting out of your comfort zone, because that's where the growth is. I show up for myself and I'm my own biggest cheerleader. Insurance is one of those industries where you can't be complacent. You have to stay current because it's affected by so many things, and if you don't reinvent yourself regularly, you're behind.

The best advice I’ve received is that hard work matters, but being intentional about how you position yourself matters just as much.

I would tell her, go for it. I promise that you will later say, I wish I had done it sooner. Don't be scared. It can be a very intimidating industry, and there's so many facets of it personal lines, property, casualty, retail, wholesale, the carrier side, the adjuster side, claims. It can be very intimidating for somebody that just doesn't know, they just know of insurance, but they don't really know what it is. But once you're in it and you get your feet a little bit under you, you start to identify either I am an underwriter, or I'm not. I am a wholesale broker, or I'm not. I think I want to do this, but I'm really better over here. And it takes all types. I've mentored people who grew from receptionist all the way to account manager, and some want to be pushed into marketing and production roles, while others are comfortable and great at being account managers. There's a path for everyone. Some people want to know how fast they can go from receptionist to account manager to account executive to inside broker to production, and there's a path for that too. My advice is, go for it. Just go for it. Be fearless, because nobody, including myself, woke up one day and said, I'm going to be in insurance, and that's going to be my career. We don't. It's not normal. But once you're in it, you'll find your place.

One of the biggest challenges in the insurance industry right now, particularly on the casualty side is that the risk environment is becoming more complex while the underlying cost of loss continues to rise. Social inflation, nuclear verdicts, expanding litigation funding, and aggressive plaintiff strategies are fundamentally changing how liability risk behaves, especially in sectors like Excess Liability and Auto Liability. Even in periods where pricing appears to stabilize or soften, severity remains a serious concern, and that disconnect creates pressure on carriers, brokers, and insureds alike.

At the same time, the market has splintered into micro‑markets. Capacity and appetite can look favorable in one segment and extremely constrained in another, even within the same account. That means program structure, storytelling, and risk differentiation matter more than ever. Clients can’t rely on “standard” solutions anymore, they need intentional, thoughtful placement strategies that reflect where the market really is, not where it used to be.

That challenge, however, creates one of the industry’s greatest opportunities. There has never been a greater need for brokers who truly understand risk, can communicate effectively with underwriters, and are willing to engage deeply in structure, contract analysis, and long‑term strategy. Insurance is no longer just about renewing a policy. It’s about helping clients make informed decisions about retention, limits, and risk financing in an evolving environment.

Another major opportunity lies in continuous learning and adaptability. The industry is influenced by economic shifts, regulation, litigation trends, and global events, which means complacency is a real risk. Those who stay curious, invest in education, and actively engage with underwriters and market intelligence position themselves and their clients far better than those who operate on autopilot.

Ultimately, the professionals who will thrive are the ones who are intentional about how they position themselves in the market. Hard work is a given, but the real differentiator is staying relevant, informed, and willing to evolve alongside the risks we insure.

The values most important to me are showing up for yourself, being your own advocate, cheerleader, and betting on yourself. I preach this all the time to the younger generation. No body is going show up for you, you have to show up for yourself, and then from that, you'll gain momentum. You have to bet on yourself, and that's what I've done my entire career. It's been scary at times, like when I reinvented the wheel this past year with CRC. Sometimes it was one foot in front of the other and I was scared, but I get out of my comfort zone because that's where the growth is. I also believe strongly in giving back and protecting your name. I say to my kids all the time, protect your name and always give back, because you never know when you're going be on the other side where you may need something or someone. I've extended opportunities to others the same way that Tammy Sherwin-Hanna and my mentor Jim Watson, gave me my first chance. Another core value is protecting my peace at all costs. What people think about me will not interrupt my peace. I tell people all the time, don't worry about what people think. Worry about how you feel about yourself. Don't let one person's opinion, or what you think they may think, interfere with your thought process or your peace. I also value being present for family while building my career. During COVID, when my brother was diagnosed with colon cancer at age 39, I was able to be present and take him to his treatments while still helping build relationships for the office I was working for at the time. I will forever be indebted to JIMCOR for their grace and understanding during this very difficult time. Even though I couldn't do a whole lot for my book of business because of several factors. I was able to connect them with a large Aggregator Group (at the time, made up for over 170 retail agents) and help develop business relationships for the company. My brother survived 9 months from diagnosis to burial, and although I didn't put a lot of dollars on the books during that time, it's the imprint, the footprint that I left that matters.