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Q&A with Ashley Stafford

Ashley Stafford, CPIA, is an Insurance Advisor with Williams Insurance Agency in Rehoboth Beach, DE. Stafford also serves on the IA&B Board of Directors and IA&B’s Delaware Government Relations Committee. In 2023, she was named an IA&B Young Agent Mover & Shaker.

Q. You’re a relative newcomer to the industry. Tell us how your insurance career unfolded!

A. My insurance career has been on the fast track from the beginning. I started as a front desk administrator at Williams Insurance Agency in June 2021. Shortly after, I was asked to start studying for my license, which I earned in October 2021. I quickly moved into an account manager role, and just two weeks later, I was promoted to supervisor, managing our high-value clients – a role I loved. Six months later, I was promoted to manager. After a year in management, I set my sights on becoming an advisor, officially stepping into that position in February 2024.

Q. What does your typical workday look like, and what is your favorite part?

A. My typical workday starts with checking emails, following up on any client inquiries, and making phone calls to prospective clients. Then I usually spend time reviewing policies or preparing quotes for prospects and meeting with them, whether in person or over the phone. I also work on reviewing renewing policies for my current clients to make sure their coverage still fits their needs.

My favorite part of the job is building relationships with my clients. I love the feeling of helping people find the right coverage for their needs, and it’s rewarding when clients trust me to guide them through important decisions. Every day brings something different, which keeps things interesting!

Q. What have you found most surprising about working as an independent agent?

A. One of the most surprising aspects has been the variety and flexibility the role offers. I’ve discovered that I’m able to work with a wide range of clients, each with unique needs and preferences, which keeps things interesting and allows me to continuously learn. Additionally, the freedom to choose the best products and solutions for each client has been rewarding, as it allows me to truly act in their best interest.

Q. You recently partnered with a local school district to introduce students to insurance agent careers. How did it go? And do you have any advice for fellow agents who are interested in volunteering for their local school’s career day?

A. Partnering with the local school district to introduce students to insurance agent careers was a fantastic experience! The students were very engaged, and it was refreshing to see their curiosity about the industry. I made sure to break down the concepts into relatable examples, like explaining how insurance helps protect things they care about—whether it’s a car, a home, or even their favorite tech gadgets. It also helped to show them that being an insurance agent isn’t just about selling policies but also about problem-solving and helping people in their times of need.

For fellow agents interested in volunteering for a school’s career day, I’d highly recommend it! My advice would be:

  1. Keep it simple and relatable: Use examples that students can connect with. They may not care about the technicalities of a policy, but they understand protecting something important to them.

  2. Be enthusiastic: Your passion can inspire them to consider the industry in a way they didn’t before.

  3. Bring visual aids or handouts: Something tangible can help keep their attention and leave a lasting impression.

  4. Engage in Q&A: Encourage students to ask questions. This often leads to fun, unexpected conversations and gives you insight into their concerns and thoughts about the future.

It’s a rewarding experience and a great way to give back to your community!

Q. You represented our Delaware members at last year’s Big “I” National Legislative Conference. What was the event like?

A. It was an incredible experience! The event brought together insurance professionals from across the country, all focused on advocating for the industry and addressing the challenges we face. It was a great opportunity to hear from key policymakers and discuss how legislation impacts our work and our clients. Being able to have face-to-face conversations with legislators and make our voices heard on issues like flood insurance reform, the Federal Crop Insurance Program, and permanent small business tax credits was truly empowering.

What stood out to me the most was the level of engagement from everyone involved. It wasn’t just about listening; it was about actively participating in the legislative process. It reminded me how important it is for us to advocate for our clients and the industry, ensuring that their interests are represented in Washington.

I’d highly recommend the experience to anyone interested in shaping the future of our industry. It’s both educational and empowering, and it reinforces the value of being involved beyond just day-to-day agency operations.

Q. This issue of Primary Agent will be published at year’s end – always a time for reflection and resolution. What has been your biggest professional accomplishment of 2024, and have you set any goals for 2025?

A. My biggest professional accomplishments of 2024 were becoming an insurance advisor and joining the IA&B Board of Directors! This milestone has not only been a significant step in my career but also an opportunity to contribute to the industry at a higher level.

I aim to continue building my clientele and fostering collaborations with fantastic organizations like IA&B. Additionally, I’m passionate about engaging with the younger generation to raise awareness of the diverse opportunities available in the insurance field, and I hope to remain actively involved in that effort. My primary goal for the upcoming year is to keep learning and growing every day, as I find that continuous development is the most fulfilling aspect of my professional journey.

Q. When you’re not working, how do you like to spend your time?

A. When I’m not working, I love spending time with my wonderful husband, Brad, our three sons –Kyler (18), Carter (13), and Kade (12) – along with our adorable dog, Rocco. We’re all about outdoor activities – beach days, fishing, nature walks, basketball – you name it!

With three teenage boys, I’ve even started playing Fortnite to spend as much time with them as possible. They think it makes me a cool mom, haha!

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