Chubb's Jennifer Riley, EVP, head of digital strategy and operations: WIL 2024

Jennifer Riley is the executive vice president, head of digital strategy and operations at Chubb. In her role within the insurer’s North America financial lines division, Riley is responsible for overall digital strategy and production of underwriting, operations, financial reporting and profit and loss performance. She continues to lead the division’s digital transformation by introducing new digital efficiencies and automation that enhance productivity.

Riley graduated with a degree in marketing and organizational behavior from Miami University in Ohio and had the opportunity to move into a Chubb training program upon graduation. 

“What drew me to the Chubb role at that point in time was that it was really a blend between an analytical role with a sales and marketing component,” said Riley. “I really started my career with Chubb from the very beginning, and I’ve been with the organization for over 27 years now.”

Prior to her current role, Riley found several opportunities to work in various offices throughout Chubb, including leadership positions in management liability underwriting, product management and distribution.

Riley was promoted to EVP and head of digital strategy and operations in December 2022. She successfully launched a new financial lines product, the ForeFront PortfolioSM on Chubb’s Marketplace digital platform, within the first year of her new role. After its launch in Marketplace, the product produced over 12,000 submissions. Riley and her team continued to improve the platform experience with new sales tools and other digital efficiencies. 

Riley also led the effort to drive the adoption of Chubb’s Cyber Central platform, a quoting platform for agents and brokers in cyber, technology errors and omissions (E&O) and standalone miscellaneous professional liability coverage. Along with other groups, she provided improvements to the platform based on external feedback. Chubb North America Digital awarded Riley with the 2023 Transformative Leader of the Year by her first full year in her role.

One of the biggest challenges she faces in her role is shifting the perception others have of using digital channels and platforms for insurance products. 

“The biggest hurdle that we continue to have to overcome is getting people to accept this channel as a viable option for their placements,” explained Riley. “How I’m viewing the digitization of our products is that we’re really entering into a new distribution channel. In order for agents and brokers to adopt to that channel, it takes a lot of change management.” 

She emphasizes that streamlining the process, like simplifying the question set, helps with overall digital adoption. 

“There’s a lot of education that we’ve been offering to our various agents and brokers to help them become more comfortable with placing their business digitally,” Riley said. “By providing a digital offering that is simple and easy to use, the whole concept of speed-to-market applies. Anything that we can do to simplify the process can also help them, I think, get over that hurdle.” 

Riley is involved with several mentorship programs. For two years, she was a formal mentor in Chubb’s Talent Champions program, a 12-month career development experience that pairs mentors with mentees for networking, skill and leadership development opportunities.

She is also a co-founder and board member of Chubb’s new North America Financial Lines (NAFL) Belong, established in October 2023, which is a DEI and belonging employee engagement initiative. 

Beyond her responsibilities with Chubb programs, Riley was a mentor for the Bridge Transcends, a not-for-profit program that supports female talent in financial lines and reinsurance, in fall 2022 and winter 2023. She was also an advisory board member with the Women Presidents Organization (WPO) from 2013 to 2019. The WPO is a professional development collective of women business leaders.

With her experience in working with young female insurance talent, Riley advises women in the industry to establish strong professional relationships. 

“My biggest advice is just to continue to work on expanding your network. Especially as you continue to advance from and move up in insurance, there are often times where you have opportunities to maybe move to different roles or areas that you may not have necessarily thought of when you first started,” Riley stated. “It really helps to have a wide network in place, not only to help you secure some of those positions, but also to give you advice and guidance on how you can continue to grow in your current career or when new opportunities come up.”

Additionally, Riley is an active executive level sponsor and participant with TechAssure, a global network of insurance brokers and experts dedicated to advancing insurance and risk management innovation. 

She encourages those in the industry to be open-minded and flexible to new opportunities, as she was when she first started her career in insurance.

“I think it’s important to recognize that you may not necessarily always know what’s ahead. That’s why it’s really important to make sure that as you move up, whatever your career path is, that you can continue to learn and advance and grow your skill sets,” Riley stated. “Take those opportunities that you have when they come.”