My name is Jahmori Simmons and I’m in insurance.
Q: Tell us about your career background.
A: My career started in the music industry, but not just on stage or in the studio—I was involved both creatively and administratively. Creatively, I’ve always been a harpist, producer and songwriter. That part of me hasn’t changed; I still actively create and perform music. Administratively, however, I worked in areas like publishing, licensing and artist development. I studied harp performance and music business at the University of Georgia, interned at the Recording Academy during my junior year and secured my first job at a small music publishing company shortly after.
Q: What drew you to music production initially, and what did you enjoy most about it?
A: Music was always in my DNA. My grandmother was a gospel recording artist, and both of my parents are music educators and musicians. My mother holds a doctorate in music education and taught in Atlanta Public Schools for more than 30 years before becoming a professor at Spelman College. My father also introduced me to music production at a young age. With a background like that, it was only natural that I found my way into the music world. What drew me to music production specifically was the process of creating something meaningful from nothing—a few sounds or ideas evolving into something that moves people. I loved the storytelling, the collaboration and the challenge of turning a vision into a finished product.
Q: What motivated you to shift from music production to a career in insurance?
A: While I loved creating music, I started to feel limited in my administrative roles within the industry. Career growth was slow and uncertain, and I found myself looking for a more structured path that still aligned with my skills and passions. I began exploring new career options where I could grow professionally while applying what I had learned in the creative and business sides of music.
My girlfriend, my now fiancée, was a financial lines underwriter at the time, and she suggested I look into underwriting. I had no idea what underwriting really was, let alone that there were roles like media liability insurance that connected back to the creative world I knew so well. Once I dug deeper, I realized media liability underwriting was the perfect intersection of business, risk and media.
Q: How did you first learn about Skyward Specialty, and what attracted you to the company?
A: During my search for roles in media liability, I came across Skyward Specialty and was immediately drawn to its focus. It wasn’t trying to be everything to everyone. The Company had a thoughtful, specialized approach that resonated with me. Even from my first interaction during the internship application process, I could tell this was a place where people cared about doing meaningful work, while also fostering real relationships. That first impression proved to be 100% accurate.
Q: What challenges did you face moving from music production to insurance, and how did Skyward Specialty support you during this transition?
A: The biggest challenge in transitioning from music to insurance was simply the knowledge gap. I was walking into an entirely new industry with its own terminology, systems and ways of thinking. Everything from policy forms to underwriting guidelines was brand new to me. It was a steep learning curve, but one I embraced fully.
Skyward made all the difference. My managers provided consistent guidance, and the team embraced me with patience and support. I never felt like I was navigating things alone. They celebrated small wins with me and gave me space to learn from my mistakes. I was encouraged to ask questions and contribute early on, which really accelerated my development.
Q: Did you participate in any formal training and development programs at Skyward Specialty?
A: As part of the internship, I completed a formal onboarding and training program that provided a structured foundation. It helped me understand the technical aspects of underwriting while also exposing me to the company’s business philosophy. Beyond that, I’ve been encouraged to pursue professional development through industry webinars, continued education and mentorship.
Q: What skills from your music production background have been most transferable to your role in insurance?
A: Surprisingly, a lot! From the business side of music, I gained experience reviewing contracts, negotiating deals and managing stakeholders. From the creative side, I learned how to manage complex projects under pressure, communicate across teams and adapt quickly.
"Producing a record and underwriting a risk may seem worlds apart, but they both require strategy, attention to detail and clear execution."
Q: How have your previous experiences shaped your approach to your work in insurance?
My background has taught me to approach problems creatively, to ask questions that others might not, and to communicate with empathy. Coming from a different industry, I’ve learned to analyze situations from multiple perspectives—technical, operational and relational. It’s helped me better understand client needs and contribute in meaningful ways, even as I’m still early in my career.
Q: How has your career progressed since joining Skyward Specialty?
A: I started as an intern and have since transitioned into a full-time underwriting associate role. The journey has been challenging in the best way—each step has helped me grow more confident and capable. I’ve taken on additional responsibilities and become more involved in strategic conversations. I’ve also started building relationships with brokers and learning how to underwrite more complex risks.
Q: What opportunities for growth and development have been most impactful for you?
A: Being given ownership of real work early on was huge. I wasn’t just doing busy work—I was actively contributing. That trust helped me grow quickly. I also appreciated how accessible leadership is at Skyward. Being able to learn directly from experienced underwriters and executives has been incredibly valuable.
Q: What accomplishments or projects are you proud of at Skyward Specialty?
A: One of my proudest accomplishments was having the opportunity to present to the Company’s Executive Leadership Team during the final presentations of our internship program. It was a big moment early in my career and gave me a chance to speak confidently about my work and perspective. More recently, I was honored to speak on the company’s Black History Forum this past February. Both of those experiences pushed me outside of my comfort zone and helped me grow as a communicator.
Q: How have these achievements been influenced by your diverse background?
A: My diverse background has played a big role in how I approach opportunities and challenges. Coming from the creative world, I’ve learned to communicate ideas clearly, adapt quickly, and connect with people from different walks of life. These skills have helped me navigate everything from high-stakes presentations to day-to-day conversations with brokers.
For example, speaking during the internship presentations and later at the Black History Forum gave me a chance to bring my perspective to the table in a meaningful way. My creative and cultural background made me comfortable thinking outside the box—and that’s helped me find my voice, whether I’m on stage, on a panel, or on a broker call. It’s made me more confident, more relatable, and more intentional in how I engage with others.
Q: What advice would you give to others considering a non-traditional career path into insurance?
To anyone considering a non-traditional path into insurance: your differences are your superpower. Don’t underestimate the value of your past experiences. Whether you come from the arts, education, hospitality, or anywhere else—there are transferable skills in all of it.
Q: How can others leverage diverse backgrounds to succeed in the insurance industry?
A: Be open-minded, do your research and be ready to learn. Most importantly, find a company that values your perspective and is committed to investing in your development. Skyward Specialty has shown me that the industry is wide open for people who are willing to grow.
Q: What do you like to do outside of work? Do you have any fun hobbies?
A: Outside of work, I still enjoy making and performing music, but I also appreciate other forms of entertainment. I’m a big sports fan and like catching games whenever I can. Additionally, I love going to concerts and traveling—whether it’s a weekend trip or something bigger, I’m always up for exploring new places and cultures.
I’m definitely a foodie. One of my favorite things to do is discover new restaurants, especially places that offer something unique or off the beaten path. Whether I’m traveling or staying local, I’m always on the lookout for great food spots to try with friends and family. And lately, I’ve been enjoying spending quality time with my fiancée, Kenza—we were recently engaged!
Q: What are your goals and aspirations for the future within Skyward Specialty and the insurance industry?
A: Looking ahead, my main focus is on continuing to build my knowledge and experience in underwriting. I want to deepen my technical expertise, expand my understanding of different lines of business, and continue growing as a professional within the industry. Long-term, I’m excited about the potential to take on greater responsibility and contribute to the company’s goals in a meaningful way.
My name is Jahmori Simmons and I’m in insurance.
This post is part of our "I'm in Insurance" blog series, where Skyward Specialty employees share their unique journeys and insights within the insurance sector. These stories provide lessons and inspiration, from career beginnings to becoming industry leaders. Stay tuned for more compelling accounts that highlight the diverse career opportunities available in insurance and what it takes to be successful.