Women in Insurance Leadership 2020

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The global pandemic doesn't have to claim all our traditions. Digital Insurance is happy to announce the 2020 class of our Women in Insurance Leadership recognition program.

Digital Insurance will celebrate the 2020 Women in Insurance Leadership at this year’s DIGIN virtual event. It’s a special opportunity to hear from the transformative women leaders who are bringing the industry into the connected future.

Join us for a world-class digital experience Nov. 30 - Dec. 4.


This year's list includes some of our first entries from the insurtech sector, with upstart carriers like Hippo and Pie Insurance represented alongside Liberty Mutual and AIG. We will be releasing their profiles in stages, linking them back to this page. But let's learn a little about each winner now.

Sarah Bennett
VP of marketing, Legal & General America
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In just two years Bennett has helped the Frederick, Md.-headquartered traditional life insurer accelerate its journey to becoming a customer-centric, forward-thinking, digitally focused insurtech and view itself primarily through this new lens. Among other accomplishments, this has included retooling the traditional carrier’s direct-to-consumer channel, accelerating the business to achieve a 55% year-over-year growth rate. See full profile
Maria Cantu
VP, property claims, USAA
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Maria Cantu, VP of property claims for USAA, is not one to settle for the status quo. In fact, she’s always pushing to innovate in ways that increase empathy in customer service, say her colleagues. Her recognition comes as San Antonio, Texas-based USAA—the third largest personal lines homeowner insurer and fifth largest auto insurer in the country—will turn 100 next year. Cantu helped develop a brand slogan for the historic event, “Excellence at 100,” to combine with the goal of providing “the most empathetic claims experience on earth.” See full profile
Melissa Eaton
VP, customer success, Pie Insurance
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A natural leader her whole life, Melissa Eaton, VP of Customer Success at worker's compensation insurtech Pie Insurance, is drawn to being very vocal, expressing her opinion, advocating for others and focused on delivering results. She says a strong work ethic and focus on relationships has opened many doors in her career. “I took every opportunity in front of me, and I was always willing to say yes,” Melissa says. “I’m driven by people, passion and purpose, and they all converge here at Pie.” See full profile
Elena Edwards
CEO, Allianz Partners USA
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Serendipity introduced Elena Edwards to insurance 18 years ago and she’s never looked back. Educated as a mechanical engineer, Edwards held several leadership positions in GE’s Aerospace and Plastics industrial divisions until she was tapped by the corporation’s financial division to pilot various insurance-related units. See full profile
Brenda Hall
EVP, Commercial Lines COO, Selective
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Life is about constantly learning, says Brenda Hall, EVP and COO of commercial lines at Charlotte, N.C.-based Selective Insurance Company of America. This constant opportunity for learning is what Hall says has contributed to her growth as an executive over her 28-year career in the insurance industry. “Every experience or opportunity I’ve had has influenced and shaped who I am as an employee, a leader and a colleague, and has helped me to be better prepared for future opportunities or challenges,” she says. See full profile
Wesley Hyatt
SVP & Manager, Workers Compensation Claims and Managed Care, Liberty Mutual
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Growing up in Massachusetts -- the state the sport was invented -- Wesley Hyatt played basketball her entire life up through and including college. When she graduated and her life took her from East Coast to West, she still expected that coaching, or perhaps law school, would be her career path. But that changed when she got a job at a California office for Liberty Mutual. See full profile
Kym McCleerey
COO, North America General Insurance, AIG
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When Kym McCleerey came to AIG in mid-2019, she brought with her a can-do, collaborative attitude and an array of diverse roles and companies within the insurance industry. Her previous experience gave her a rich knowledge of the insurance domain, and a unique ability to understand and work with cross-functional teams. Throughout her insurance industry career, she’s taken on new and challenging roles, beginning on the business side at One Beacon Insurance, leaving the carrier side for a software startup, and finally winding up in her current position as COO or AIG North America General Insurance. See full profile
Nicole Perrault
Chief risk officer, Hippo
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Today, Nicole Perrault is chief risk officer for Hippo -- the home insurance insurtech that is one of only a few billion-dollar “unicorns” in the sector, especially on the P&C side. But her ability to stand up new concepts to meet coverage needs was honed a decade ago, at the recently launched Narragansett Bay Insurance Company, which entered an underserved market of coastal homeowners to deliver coverage capacity that hadn’t been available before. See full profile
Denese Ross
Chief underwriting officer, Motion Auto
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Denese Ross’s insurance career covered a lot of the typical nuts and bolts of insurance during stints at Commerce Insurance and CSAA, among others. But it was in her second stint at the latter that she had an “a-ha” moment that set off the chain of events bringing her to usage-based insurance MGA Motion Auto, where she is chief underwriting officer today. See full profile
Tawana Scott
VP, Commercial Insurance Product, SageSure
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With more than 30 years under her belt in the insurance industry, Tawana Scott’s professionalism and skill has brought her to the position of VP for Commercial Insurance Product at SageSure. Her colleagues say the can-do attitude she brings to the table helps facilitate positive change and growth within a fast-paced, quickly expanding company. See full profile