Ashley White Reveals Why Black Pros Should Look at Insurance

Most people stumble into the insurance industry. Ashley White is the first to admit he did too.

After building a career as an executive in Fortune 50 retail companies, a layoff forced him to reconsider his path. The transferable skills he had built  strategy, storytelling, partnerships, big business operations turned out to be exactly what the National African American Insurance Association needed. Two years into his role as Chief of Staff, he has no plans to leave.  He is building the pipes for NAAIA’s next 30 years

NAAIA, which most of its members simply call Naya, was founded nearly 30 years ago by a Black insurance agent who walked into a room and recognized a representation problem. That founding moment has since grown into an organization with more than 3,500 members and 33 chapters nationwide. Now, as the organization prepares to celebrate its 30th anniversary and host its 2026 Rooted to Rise National Conference in Charlotte, North Carolina from September 22 through 24, White sat down to talk about what the industry gets wrong, what it takes to rise into leadership, and why the work is far from finished.

For viewers learning about NAAIA for the first time, what is the organization all about?

Our founder walked into a room almost 30 years ago and recognized a representation problem in the insurance industry. As an agent and business owner, he understood that insurance is about protecting families, building assets, and creating generational wealth  and he wanted to bring those opportunities into the communities he served. That founding mission has since expanded to include professionals across all business functions: corporate employees, lawyers, learning and development professionals, and entrepreneurs. In short, we build the toolset for experienced executives, mid-level managers, and recent college graduates who need to see insurance as a viable career path.

What does the Chief of Staff role actually look like on a daily basis?

The Chief of Staff role looks different depending on the organization. Here at NAAIA, I am a jack of all trades. Strategy execution, talent support, partnerships  I have a hand in all of those things. Designing the future is where I believe I am most utilized. As we approach our 30th anniversary, my role is to take the vision from our CEO, serve as his proxy when needed, and make sure our team is driving in the right direction to build the processes and pipelines needed for the next 30 years.

NAAIA has grown from a single founding moment to 33 chapters and 3,500 members. What does that growth tell you?

The growth confirms that the need for this work is real  not just for agency owners, but for the large corporations whose names appear on stadiums and in commercials. Progress has happened. However, the data also shows us clearly that the work is not finished. There are still individuals in this space who may not look like us or who carry other dimensions of difference that this industry was not historically designed for. By breaking down those barriers, we help others beyond our immediate community. We celebrate the chapters and the membership, but we cannot stand on those laurels for too long. The work continues.

People hear “insurance career” and immediately think of selling policies. What are they missing?

Most insurance professionals will tell you they tripped into this industry. They did not start as agents or brokers. Many came with transferable skills from finance, law, communications, marketing, or human resources and discovered that all of those skills translate directly. Every major insurance carrier running national commercials has marketing professionals building those campaigns. HR executives are still leading people inside this industry. Technology professionals are reshaping underwriting and claims. Finance operators are central to how this business runs.

Furthermore, insurance is global. Coverage touches everything from the device protection a cashier offers you at checkout to international business risk. The industry is far larger than most people realize on a daily basis. We tell people: you already have the skills, and we are open for you to bring them into this space.

You mentioned tripping into the industry yourself. What is your story?

I grew up in retail and became an executive at Fortune 50 companies. After a layoff, I had to think differently about where my skills could land. Retail felt uncertain given the macro environment, so I started making new connections. The strategy experience, public speaking, partnership development, and big business operations I had built over the years turned out to fit perfectly with the Chief of Staff role at NAAIA. All of our partners are large corporations, and being able to speak their language and bring them into meaningful conversations was something I was already versed in. I have been here two years and have no plans on leaving.

What does it actually take to build a lasting career and rise into a leadership seat?

I think about this in three groups. First, there is the talent acquisition side  getting people in the door. Second, there is keeping people long enough to grow and earn promotion. Third, there is the extension into executive leadership. NAAIA has specific academies for each of those groups: emerging leaders, mid-managers, and executives sharpening their skills.

On the individual level, performance is only the admission ticket. Getting to the next level requires sponsors, not just mentors. Many professionals in our community have mentors but lack sponsors who will put their name behind an opportunity. Additionally, the projects that come to us are often the hardest ones in the company, where failure rates are high. Failing in those spaces can close doors if the right relationships are not in place. Learning to fail and recover is one of the most critical skills any executive needs. Nobody is born with that skill  you build it through experience. The people around you have to give you the space to develop it. That is a big part of what our programming is designed to provide.

What important work is happening behind the scenes at NAAIA that the public rarely sees?

The most important work is building the pipes for the future. Celebrating milestones matters, but the harder work is identifying what skill sets and building blocks are needed to get us to the next 30 years  whether that is technology, leadership development, or expanding the pipeline to receive and grow talent. Members might attend one webinar and see the output, but the team is constantly running in the background asking what comes next. Our members have real, evolving needs. Serving them now and anticipating what they will need in the next 30 years requires work that does not always generate excitement, but it is absolutely necessary.

Let’s talk about the 2026 Rooted to Rise National Conference in Charlotte. What conversations need to happen in that room?

This is what I am most excited about. The conference brings together multiple tracks designed for different career stages. Emerging leaders get programming that tools them up for their next steps and keeps them engaged. Agent and broker sessions focus on writing more business, because strong businesses build strong communities and strong communities build strong cities. Executive sessions address what leadership still looks like at the top and how those leaders can reach back down to elevate others.

Beyond the sessions, we are committed to investing in Charlotte while we are there. We are directing members to local businesses, restaurants, and cultural experiences. We want to make sure our economic presence in the city benefits the community, not just the conference hotel. The history of Charlotte  post-slavery, arts, culture, sports, economics  is something we want to honor and engage with while we are there. We will have a party, but we will also be doing meaningful work and genuine community investment the entire time.

There is also a career fair with more than 60 employers, open to the public. What should attendees do before they arrive?

Be ready. We have done our part by putting the right players in the room. Over 60 employers will be there. Attendees need to come hungry. Come ready to have real conversations, not just collect business cards. Come ready to build business, build community, and invest in yourself. The relationships you build in that room are the ones that can change the trajectory of your career. We will facilitate the engagement, but what people leave with will depend on how prepared and present they are when they walk through the door.

Why was Charlotte the right city for this conference?

Charlotte checks every box. Some of the largest players in the insurance industry have headquarters there. The city has rich culture, food, music, and arts. It is ready to receive us. When we look at the cities where we can do meaningful work and also invest in the community around us, Charlotte rises to the top. We are excited to be there, and I believe I speak for the entire NAAIA membership and leadership when I say we cannot wait.

As NAAIA approaches its 30th anniversary, what must the organization remain rooted in — and what must it be willing to change?

What we cannot lose is our members. Inside our membership are decades of experience, landmark agency owners who are fourth and fifth generation, and brand-new graduates starting their first careers. Staying aligned to the full range of those needs is how we remain successful. The roots are our people and the trust they place in us.

At the same time, the rising part of our theme requires us to evolve. Artificial intelligence is reshaping this industry. Our leaders need the tools to navigate that shift. Underwriters, HR executives, and technology professionals all need to be ready to lead regardless of what comes next. Rooted to Rise means honoring where we came from while building aggressively toward where we are going.

The NAAIA 2026 Rooted to Rise National Conference takes place September 22 through 24 in Charlotte, North Carolina. The career fair and marketplace are open to the public on September 22.

Visit naaia.org for the full agenda, conference registration, and membership information. Find NAAIA on LinkedIn by searching the national organization directly.