Triple-I Blog | From Start-Up to Industry Leader: Casey Kempton’s Trailblazing Career – Go Health Pro

By Michaela Platt, Communications Coordinator, Triple-I

As businesses started incorporating Internet strategies into their operations, Casey Kempton had just begun her graduate studies in cognitive anthropology and was working for a tech startup. A Connecticut native, Kempton had always been aware of insurance giants based in her state.

So, when the startup she worked for went out of business, a career with their insurance partner, The Hartford, seemed a natural fit. She applied for a position in their e-business ventures unit and has worked in roles across the insurance industry ever since.

“When I first came into the industry, learning about exactly what our product does and how it benefits consumers, I had this sense that both agents and consumers could expect more from their carriers,” said Kempton, who is now president of personal lines at Nationwide.

To Kempton, this meant thinking about preventing or minimizing claims, in addition to optimizing the end-to-end experience with the product. The curiosity and drive for innovation that marked Kempton’s early career propelled her to patent two home insurance risk rating solutions.

“A small group of us wanted to take the concept of early telematics and figure out – if and when the internet was pervasive and everything was connected, as they were predicting,” Kempton said. “In this future model, how could it impact real-time rating, monitoring, and response?”

Kempton leads all aspects of the business, including product, underwriting, sales and distribution, claims and services. She previously was executive vice president and digital business officer at Chubb and spent time with ACE Group, accountable for global personal and commercial lines and leading operations and information technology for Latin America.

The result was a product Kempton helped create while still in her early twenties :a closed-loop system that senses, underwrites, and prices risk in real time while also offering remediation services. The system has now been patented for nearly 20 years.

Despite this promising start, Kempton faced obstacles in this traditionally male-dominated field. Even as she rose into leadership roles, some challenges persisted.

“There are times where I may have traveled to visit agents or partners in different parts of the country and realized that expectations on the roles that women could hold versus men were quite different,” she said. “I had several experiences where it was assumed I was the note-taker for the meeting when, in fact, I was the boss or the most senior person there.”

Despite the challenges, Kempton has found her career as a woman in leadership to be incredibly rewarding and is thankful for the mentorship and sponsorship along the way.

“I had two really important mentor-sponsors in my career, both of whom were men, both of whom created opportunities for me that, on my own, I might have struggled to have,” she said.

Kempton has worked to form alliances and a support structure with both men and women in the industry. She has also found herself in stages of her career where she was without a mentor and had to network and build new relationships. She emphasizes the importance of leaning into common ground and building bonds with coworkers while also establishing practices that amplify all voices at the table.

“If you contribute something and then one of your male counterparts takes credit for it five minutes later, nobody says anything,” she said. “Everybody heard you and they know you said it, but we don’t have a practice of saying, ‘Right, that’s the idea Casey just shared. Thank you for pointing that out.’”

Kempton said a lot of bright, capable, driven women assert themselves – only to be  labeled “difficult”, “aggressive”, and “hard to work with”. That is something she has coached a lot of women on through her career.

Kempton also addressed the pay gap, and the unspoken penalties women face for taking time off to have children.

“I still have these stress dreams,” she said. “I know I’m stressed about something when I have this dream, and it’s that I’m pregnant again. And my goodness, what is that going to do to the rest of my career? How am I going to manage that? To me, this correlates to the pay challenge because my career paused with the birth of each of my children.”

Kempton is passionate about addressing the pay gap in the insurance industry, but recognizes that there is no easy answer.

“Each manager must make a personal commitment to say, ‘I can’t tell them how underpaid they are, but I can work to fix it over time,’” she said. “We need to work to fix it every year until men and women are on par. We need to create awareness with managers, that they have some control over how we address that pay gap.”

Meanwhile, women executives like Casey Kempton continue to break barriers. Her journey highlights the power of innovation, perseverance, and the importance of mentorship and allyship. From her early days at The Hartford to her leadership role at Nationwide, Kempton’s story is a testament to the impact one person can have.

“For me, leadership has been incredibly rewarding,” said Kempton. “The best advice I can give to young women starting out is to be curious. Expose yourself early on to as much as you can contextually and then become an expert in something. Being more intentional about how you navigate where you want to go, that’s when you’ll go far.”

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