How women in insurtech can maximize mentoring

In almost every discussion about how best to elevate more women into leadership positions or empower women founders, the topic of mentoring comes up. In her bestseller Lean In, even Sheryl Sandberg said women should be mentoring other women (among many other interesting tidbits of advice). But, it’s been my experience that mentoring very rarely works for a multitude of reasons.

Recognition of Women’s History Month, International Women’s Day, and promoting diversity in leadership is especially important in insurance considering the relatively low numbers of women leaders in the industry. It’s even more important among tech companies where women leaders make up less than 10 percent of today’s founders and CEOs. One might think this makes insurtech the perfect environment for perpetuating a male-dominated leadership structure, but women in insurtech are actually holding their own, so to speak.

While mentoring is by far the most popular mechanism for accelerating women into the C-suite, there are other ways to do it. Unfortunately, those opportunities are not always immediately obvious or available. This leaves many companies implementing mentoring programs with ineffective weekly meeting requirements and blanket program goals. I recently asked some women leaders and friends about their experiences coming up through the ranks in insurance and technology, with mentoring in particular, and how they are “paying it forward” today.

All that said, the journey to success, and the degree to which mentoring plays a role, is different for every woman founder or leader.

“I believe hard work and luck are responsible for success, and likely in equal portions,” said Jennifer Linton, founder and CEO of Fenris, an insurtech that uses APIs to deliver front-end insurance data through alternative data and machine learning (ML) to insurance and financial services companies. “But, in the end, it comes down to people taking a chance on you, your company, and your product. No one person is ever a success without the help of all the other people involved along the way.

Jennifer Linton, Fenris

“My greatest mentor has been Larry Rosenberger, former CEO of Fair Isaac who oversaw the adoption of the FICO score in the 90s,” Linton continues. “We speak regularly and he takes on a variety of roles as advisor, challenger, and helps me hold myself accountable. He has believed in me at times when I felt battered and felt my belief in myself wavering, and that bolstered me up and propelled me through. Because of his experience, he was able to help me identify blind spots and he shares his frameworks before stepping back to let me decide and act. I’ve become a better leader through his example.”

Linton’s success has launched three startups, including DriveFactor (now CCC Drive), Elephant Auto Insurance, and Fenris. With the help of mentors like Rosenberger, she is leading the Fenris team to be an industry leader in data, scoring, and technology to support sustainable, customer-centric growth in insurance and financial services.

Amy Nebons, founder of Blink Events and BOCS DSM, shares Linton’s sentiments about hard work, luck, and the value of mentorship.

“Mentoring has been monumental in my business journey,” said Nebons. “I have always been keenly aware of the areas where I need guidance and I actively seek out people who can help me hone the skills I am lacking. No entrepreneur can do the job alone. We need other people to help point out our blind spots, provide a different perspective, and sometimes even provide emotional support.”

Having been the sole proprietor of an event planning and event management company when the pandemic really hit its stride in early 2020, Nebons is no stranger to asking for feedback on business trends and her latest ideas. She launched BOCS DSM, a boutique custom corporate gifting company which curates and delivers elegant gifts for employees or customers in order to create positive brand experiences and promote engagement in a time when it’s become difficult to engage face-to-face, and is working hard today to scale the business in downtown Des Moines.

For Wendy Aarons-Corman, CEO of OWIT Global, a startup microservices firm focused on the property and casualty (P&C) space, success has always been about cultivating a “growth mindset” through continuous learning and the transformation of the advice and support of mentors into action. Her career has been an interesting mix which ranges from founder and SVP of Business Development for Duck Creek Technologies and president of edgeIPK to founder of her own consulting company, Corman Consulting.

Wendy Aarons-Corman

“My mom was my first mentor,” said Aarons-Corman. “She was easily the most intelligent, insightful and supportive person in my life. She went to college and had a great career, opening her own business late in life. In my work life, I mainly had men as mentors. These men saw my potential and provided me with opportunities and challenges that helped me grow.”

Because her mentors helped her never feel different or “subpar,” Aarons-Corman is equally comfortable today in startups and large corporate environments and is putting her lessons learned from mom and mentors alike to work on a day-to-day basis.

“I learned early on that it is important to ask questions and to not draw conclusions,” said Aarons-Corman. “This exercise helps in promoting patience and learning to work with others. The other factor is being comfortable with your weaknesses and learning from your mistakes.”

As opposed to Nebons, Linton, and Aarons-Corman, Sandy Dougherty, director, insurance, for digital payments company, Exactuals, didn’t necessarily have strong mentors as she climbed the corporate ladder, but always internalized guidance from friends and colleagues when possible.

“A direct supervisor, very early in my career, gave me the most valuable piece of advice,” said Dougherty. “He said to me ‘never bring me a problem without bringing me a solution.’ This one phrase has shaped my entire life. Additionally, I always try to be true to who I am and I have a strong desire to always understand the ‘why’ of things. That doesn’t always make me popular with those that like the status quo.”

Sandy Dougherty, Exactuals

Dougherty held leadership positions with a mid-size BGA and One America Financial Partners before starting her own consulting company and taking charge of the insurance practice and development of corporate accounts at Exactuals. Because of her unique leadership journey, for Dougherty, it’s not important whether you put a formal label on mentorship or not.

“I try to be a ‘quiet’ mentor to all my teams,” said Dougherty. “Knowing where you want to go and having a solid plan to achieve your goals will bring you success. I truly enjoy watching my employees succeed by giving them the opportunity and tools to achieve their goals.”
Kerry Crockett just recently came to the insurance industry from a position in medical resonance imaging as the current CEO of IASA (formerly the Insurance Accounting & Systems Association), a membership-based, not-for-profit association focused on education and networking within the insurance space. In moving from one industry to another, Crockett is rediscovering mentorship and believes it can be a success factor when done right.

“Things can change quickly and you have to stay on top of what’s happening so that you can be proactive vs reactive,” said Crockett. “Staying current in the latest technologies and trends also be to be better positioned to respond. Mentoring is most effective when both parties are actively engaged in the process. It’s definitely a give and take and both have to be willing to be vulnerable for growth.”

While the world absolutely needs more diversity in leadership, the experience of women with mentorship as a means of accelerating the journey to the C-suite is far from uniform. Perhaps the best bit of advice any young woman aspiring to leadership in the insurance industry can take from the expertise of Aarons-Corman, Crockett, Dougherty, Linton, and Nebons is to be an active participant in your own career. Ask people you respect to mentor you instead of waiting to be “assigned” to someone you don’t know. Proactively identify learning opportunities along the way. Recognize and reward those around you for their skills, achievements, and efforts as you build your own tribe. Choose your own adventure.