The insurance industry is changing fundamentally. Market pressures from the rapidly growing group of digitally native consumers crossing over into adulthood, are driving carriers to make changes in how they go to market, what products they provide, and how they look at leadership.

That’s why this year, In addition to our traditional WIL program, Digital Insurance launched Women in Insurance Leadership: NEXT this year. We asked senior executives at insurers to nominate leaders they’ve identified, under the age of 40, who have the confidence of their organizations that they will be able to steward the company through insurance’s evolution. Then we asked them to talk about their young careers, and to look forward at what’s to come.

That’s because the book on these women is still unwritten. NEXT honorees are at the outset of a journey that is equal parts uncertain and exciting; a path that they will forge in part by drawing on both the wisdom and institutional knowledge of WIL trailblazers and on their own instincts.

WIL NEXT winners share several characteristics. They are solidly members of the Millennial generation; members of a cohort that has been courted since coming of age in the years following the 2008 economic meltdown. That means their adeptness in working in a digital environment is of major value to the insurers trying to adapt. “Even the value proposition of an insurance company has the potential to shift from risk taking to risk prevention – this means that we as young leaders have the opportunity to question the status quo with credibility,” says Kassie Bryan of Swiss Re.

They also feel a duty to challenge established views of the industry. “I had no idea what insurance was beyond a ‘good idea’ for those who could afford it,” says Bestow’s Julie Yang. “We believe strongly in the moral obligation we have to correctly underwrite the consumer and protect their data, and I hope that this discussion leads us to a future where data is not a dreaded word, but a welcome One that is used to make all our lives better.”

WIL NEXT honorees, like many of their peers, represent the first executive in their industry to have digital strategy at the forefront of their careers from day one.

“Having the opportunity to participate as the industry evolves in the digital age and the risks continue to change has been really rewarding,” says Travelers’ Heather Cavallaro. “It’s changing trends like these that make the industry so exciting, because a decade ago, leveraging design-led thinking, customer feedback and behavioral metrics was not as commonly discussed. And I know in less than five years, I will be talking about a new topic that’s imperative to our future success.”
Kassie Bryan; Head of solutions for P&C, Americas; Swiss Re
Kassie Bryan, Head Solutions North America, Swiss Re
Kassie Bryan leads the team at Swiss Re responsible for defining Swiss Re’s insurtech partnership strategy. This included developing a road map to help interested startups navigate large, complex organizations like Swiss Re and other insurers. She and her group also has developed analytics offerings for Swiss Re’s insurance clients; one in particular incorporated behavioral economics to help reduce policy lapse. Nominated by Keith Wolfe, president of U.S. P&C, Bryan was previously part of Swiss Re’s M&A team.

What is your favorite part of working in insurance? What do you think the industry could do better?
Knowing that I am helping make the world more resilient. It keeps me motivated to know that the work I do enables entrepreneurs to take risks and families to get back on their feet after catastrophes. I think this is an aspect of insurance that resonates with many people, and is one of the draws to working in this industry. On the other hand, I think insurance is viewed as outdated and cumbersome – particularly the policy forms we use and the paper trails that are frequently still relied on. This reputation means the excitement of insurance as an industry isn’t understood more broadly, and we are struggling to bring in young talent compared to other industries.

What personality trait do you see as helping you find success in your career thus far?
Curiosity and a love of learning new things have driven me to push myself to grow in new areas and dive into each job with an excitement for developing new skill sets. Each new job has had a steep learning curve. For example, when I began my role with Principal Investments & Acquisitions, I had no finance background — I was a political science major looking to become a lawyer — but found I loved the logic of balance sheets and strategic thinking of investing, and took outside accounting classes to strengthen my understanding of corporate finance. Now in Solutions, one of my favorite parts of my job is learning every day about emerging technologies and tracking the waves of change that are transforming the insurance industry.
Heather Cavallaro, second VP, Travelers
Heather Cavallaro, second VP, Travelers
Heather Cavallaro is recognized for her work in building an integrated customer experience across Travelers. As leader of the business insurance digital team, she and her team have partnered with technology and business leaders across the company to deliver increased self-service capabilities through online channels. Nominated by EVP Mojgan Lefebvre, Cavallaro is also known within Travelers for mentoring Travelers interns and Leadership Development Program participants.

How have role models and mentors helped you on your journey in insurance?
I have had the opportunity to work with and continue to work with so many admirable leaders and technologists. What stands out for me is one of our female Vice Presidents who encouraged me to bring my whole self to work. She modeled for me that it was always okay to stand firm on your principles and beliefs and that I did not need to conform (i.e., cut my long hair) to be an executive (14 years ago, I couldn’t find a senior female with long hair). She also taught me it was okay to be vulnerable, share authentic stories about who I am and helped me lose the fear of being judged by others.

What’s a myth about insurance you are hoping to challenge?
It’s not yet common knowledge that technology in the Insurance industry is super exciting. From a digital perspective, we have vast opportunities within Insurance, including leveraging digital ecosystems more in our distribution strategies, data and analytics to augment and expedite underwriting, and the use of Internet of Things and sensor-based insights to help prevent losses. Technology is becoming more ingrained in our business strategies rather than being treated as a separate organization that supports them.
Elizabeth Henderson, senior managing director, Aon
Elizabeth Henderson, Sr. managing director, Aon
A specialist in catastrophe risk, Elizabeth Henderson has become a leader in leveraging digital in her time at Aon. She was the business leader on Analytics Dashboards, identifying the tech partners to help develop a web-based, interactive reporting system that gives Aon clients access to a wide variety of insight. Henderson also invested in workflow automation for the catastrophe group, isolating bottlenecks that could be mitigated with technology. Nominated by Dan Dick, executive managing director, Henderson also sits on Aon’s Diversity & Inclusion Council.

How do you view your leadership strategy?
I have built a team of some of the most skilled catastrophe risk analysts in the industry and we are constantly finding new insights and analyses to share with our clients. The key to curating a successful analytics team, though, is keeping the focus on the practical applications of what we are presenting. How will a new product help our clients grow? Are we able to articulate the value of our work to our clients? Are we delivering our work in a way that will drive the most actionable insight for clients? Those types of questions help me to stay focused, and keep the team focused on delivering results.

Is there a mentor that helped you develop that strategy?
Kristi Wilts, the head of analytics operations for the U.S, is an operations superstar and a seriously brilliant woman. While I was an early proponent of investing in automation for cat modeling and had a strong vision of what a future cat modeling group would look like, I needed a partner like Kristi to figure out how we would actually accomplish it. She pushed me to spend more time in the initial phases of the project to build consensus within the team, and collect the data needed to set strong KPIs. She taught me that with the right focus and passion I can get the buy-in needed, even from people or teams who I thought would never get there.
Kelley Kage, senior director legal technology, Liberty Mutual
Kelley Kage, Sr. director, legal tech, Liberty Mutual
Kelley Kage has become a star at Liberty Mutual for her ability to manage big, complex digitalization projects. As director for third party services in global retail markets, she led an application integration initiative to streamline the combined Safeco and Liberty Mutual systems. Now in corporate functions technology — specifically, legal technology, she is in the midst of transitioning the group to Agile methodology, and has already delivered minimum-viable products leveraging data to power machine learning. She was nominated by group CIO Shelia Anderson.

How do you stay focused while in the midst of major projects?
Remaining calm and having a vision for myself and my team has been critical. There are fire drills every day, but being able to never lose sight of the important work that will really drive change in the organization is important. In one case, a vocal leader in the organization had drafted a solution, was soliciting feedback, and was ready to hit the ground running on implementation. We sat down, I expressed my concerns, and made some recommendations for how to proceed to enhance the value delivered. Initially this other leader was very resistant. By remaining calm, and communicating clearly the reasoning behind my recommendation, we were able to come together and develop a better solution that improved process, enhanced data quality, and simplified the way users thought about their work.

What do you like about working in insurance?
You can work for one company for 20 years, but it feels like you have worked at five different ones because when you move around the organization, the business is different, the customers are different — really, everything is different. Also, so many areas of insurance are ripe for technology enhancement, and I believe that the Insurance industry is on the cusp of major disruption. Insurance is a complex product, but innovation comes from taking something complex and making it awesomely easy.
Julie Yang, Product manager, Bestow
Julie Yang, Product manager, Bestow
Julie Yang’s official title is product manager, but according to Jackie Morales, the chief insurance officer of Bestow who nominated her, a better description is CEO — of the company’s enrollment platform, at least. Yang is described as a tenacious, optimistic presence in the company who has delivered the digital enrollment platform on which the company’s value proposition is placed. Since she joined Bestow and began guiding the project, the company’s daily sales are up 40%.

Can you talk about a crisis that helped you become a better leader?
I’ve certainly had my fair share of “learning curve” experiences. I inherited expectations and timelines, or sometimes lack thereof, on which I never signed off but could not change given the nature of the work and who I was at that point in time. The team was several months late in delivering a product, but we were finally about to launch, when I found a critical feature had not been built out. Through that period, I learned to ask for time, to voice what might be unpopular opinions, and most importantly, to walk around people or situations instead of letting them impede my progress. Resilience, to me, in other words is a mantra to “be better:” Identifying what went wrong and chasing down what can go better. It is not letting my ceiling become lower for fear of failing; it is cresting with the rising tide to experience the joy of ever greater success.

How have leaders in the company helped encourage you through rough times?
Jackie Morales, who nominated me for this award, dropped handwritten cards for me and the engineering manager who was running the launch of the new product with me. At that time, we were both surprised because we thought we had simply been doing our jobs, but this gesture made us take stock of what we were doing and feel recognized for our contributions. I realized that, at least for me, it had sometimes felt like a very lonely mental journey, and that echo from the dark was exactly what I needed to make it easier.