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Wisdom, Wit and Women: Insurance Leaders Share Experiences 

It’s the feel-good hit of the summer, at least for business conferences. For the past ten years, the Women in Insurance Leadership conference has offered an opportunity for some of the best and brightest industry leaders, like The Hanover’s Cilsy Harris, who won in ’16, to share their insights and experiences with their peers, as well as with up-and-comers.

The fact that WIL continues to grow — more than 50 women out of some 300 identified themselves as first-time attendees — is a testament to the pent-up demand for inspiration, mentoring, and maybe most of all, visibility among high-achieving professionals who just happen to be women.

SMA's Deb Smallwood hosts a panel of 2017 WIL Winners
SMA’s Deb Smallwood hosts a panel of 2017 WIL Winners

After the introductions and awards ceremony, President and CEO of Strategy Meets Action (SMA) Deb Smallwood got the event moving, hosting a panel with 2017 WIL winners: Linda Roubinek, Executive Vice President and Chief Customer Interactions Officer at Grange Insurance, Dawn Sly-Terpstra, Assistant Vice President of Marketing and User Experience at Grinnell Mutual, and Michaele James, Chief Technology Officer at CSAA Insurance Group.

In a lively discussion, these accomplished insurance industry executives opened up to offer advice, and the benefit of their experience, to the crowd, including:

  • Look for that “stretch assignment,” and don’t wait until you’re 90 percent qualified. Go for it, even at 20 to 30-percent qualified. Act as if you are in that role, and you’ll become it.
  • When problem-solving, use the right tool for the job. Hint: It shouldn’t be a jackhammer every time.
  • During any tough conversation, make sure that the other person also “wins.”
  • Get involved in your community, network, and seek mentors both inside and outside your company. These suggestions become more important the higher you climb.
  • On management style: Read “Level 5 Leader,” and focus on results while you nurture your team. Contrast this with the old way: “Be just like the men: be a bull.” Instead, be a “servant leader” – meaning be present, accepting, vulnerable, and useful.
  • The more senior you become, the less stock you should put in your title.

The panel also discussed digital transformation and the fact that it is both exciting and terrifying. They seemed to agree that culture may be the single biggest challenge, in part because so many top leaders in the insurance industry have so little experience in other industries. This is an important point that several women echoed, most notably Susan Sachatello, who previously was a marketer at Victoria’s Secret and brought direct-to-consumer expertise to her role as Senior Vice President at CUNA Mutual Group.

Melanie Henderson, Executive Director at E&Y, asked some hard questions, including:

  • Why are so few women leading insurtech startups? The truth, she said, is that there’s no good answer to the question.
  • How will legacy carriers, with their old, hierarchical cultures, adapt to digital imperatives? Willingly or not, they will have to, because the old way just won’t work any longer.
Marisa Buckley spoke from hurricane-hit Florida
Marissa Buckley spoke from hurricane-hit Florida

In a day packed with strong, accomplished, and eloquent speakers, Marissa Buckley, the keynote speaker and Vice President of Marketing at Florida’s Security First Insurance, was especially compelling. In the wake of Hurricane Irma’s devastation, Buckley wasn’t able to attend in person and presented “What it takes to Transform Digitally” via Skype.

Fully 37 percent of claims were coming in electronically, she said, compared with 20 percent for previous storms. The company’s transformation enabled it to move its claims team to Atlanta. They hired 1,000 temporary workers, sourced via social media, to process an expected 4,000 storm-related claims per day. The transformation and integrations work that they had done helped big time, she said.

With so much press and valid criticism about the challenges women face in the workplace, like “Why Do Women Bully Each Other at Work?” and “Why Is Silicon Valley So Awful to Women?” both of which recently appeared in The Atlantic, it’s genuinely refreshing to see so much positivity.

While we all hope to see more female insurtech leaders, as well as their contributions toward insurance’s digital future, women can — and do — reach senior leadership levels in the insurance industry, and our numbers are only increasing. Mentoring is common and encouraged. We are visible and successful, and looking forward to an even greater turnout next year.

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