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How to advance in your insurance career: Advice from 6 Arrowhead women leaders

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Having an adept workplace mentor is invaluable - not only to coach you through sticky situations, but also to help you seek new opportunities and strengthen your insurance career path. In the spirit of International Women’s Day earlier this month, we’ve gathered some great advice from female leaders across the Arrowhead family to help you be a better co-worker, supervisor and leader. Their tips just may help propel you into the next stage in your insurance career.

First, let’s meet these ladies. Stacie Pirrone is ACM’s director of operations and wanted to be in theater when she grew up. Jamie Cox, commercial lines service manager of Auto Aftermarket in Overland Park, dreamed of being a princess and a lawyer. Cheryl Haas, underwriter 1 for Workers’ Compensation, also wanted to be a lawyer. Becky Pinto, president of Workers’ Compensation and Colleen Miller, underwriting manager in Carlsbad, both wanted to be teachers. Deirdre Gonzalez, president of ACM’s Workers’ Compensation division, wanted to be a singer, fancying herself as the next Olivia Newton-John.

Ironically, none of them ever said, “I want to be in insurance when I grow up.”

Here are two questions we asked them and their replies:

Who was a mentor or was extremely helpful along the way for you? What did they teach you?

“A previous supervisor taught me to work hard, work smart and it will pay off,” said Colleen Miller.

“I’ve had some great mentors and some not-so-great bosses, but I learned from all of them,” said Jamie Cox. “They helped me learn what kind of leader I DO want to be – and DON’T want to be. One mentor at Farmers helped me network and often played devil’s advocate to stretch me (‘Why did you choose this course of action, what was your thought process?’). One other tip I learned early on: Always have your resume up-to-date and periodically send it out to see what you’re worth.”

“My father taught me from an early age to work hard for the things I want, never take responsibility lightly and to present myself in a way that clearly demonstrates my desire to advance,” said Becky Pinto.

“Deirdre Gonzalez interviewed me many moons ago and since then she has never left my side,” said Stacie Pirrone. “She has taught me many things but one that I keep as my mantra as of late is – be smart, be kind, show grace and be brave.”


What lessons have you learned along the way that you can pass along as advice for career advancement?
  • Purposefully plan your career path. Don’t stay in the same spot because it’s comfortable – it can become a rut. Be willing to learn and not be scared to take chances. Step outside your comfort zone, says Jamie Cox.
  • Happiness starts with yourself. You choose it; don’t allow the day and its circumstances to choose it for you. “If you get discouraged, don’t give up, sometimes you just have to step away for minute,” says Colleen Miller. “Show up as you are, do the very best you can with no apologies, and leave with a smile on your face. Lean into the situation and then escape with your integrity… and your skin still intact,” added Stacie Pirrone.
  • Set priorities and non-negotiables. Jamie Cox says she always tries to focus on her team: are her decisions and actions helping or hurting? “My job is to look at the bigger picture, to ensure my team has everything they need to do their jobs, that communication is flowing and transparency is evident. As my team becomes increasingly busy, am I taking care of them?”
  • Being a leader doesn’t necessarily mean becoming hardened and calloused. Yes, leaders must make the tough calls. Yes, that often means someone isn’t happy (perhaps the entire team). However, “when I learned that the vulnerable and compassionate side of my personality could be a strength instead of a weakness, I became more comfortable in my own skin,” said Becky Pinto. “This helped me to begin to understand others’ needs, their strengths and areas where they could grow and improve. We all have inherent traits that we often consider to be a weakness, when in truth they could be your greatest strength.”
  • Get into the trenches with your team – consistently – to earn respect. They need to see you in the trenches, when times are tough and everyone else is getting fired upon, says Jamie Cox. No armchair quarterbacking. Take more than your share of the blame and take less of the credit.
  • Take advantage of learning opportunities. Cheryl Haas readily admits that when she started at Arrowhead, she had zero knowledge of insurance, except for her own personal coverage. Jumpstarting her insurance education with the Insurance 123 class, she moved from a personal lines data processor to a commercial lines CSR (customer service representative). To further her career, she took two AU classes, received her AU designation and was promoted first to the submissions team and next to the auxiliary team, working in compliance and classification assignments, and now as an underwriter 1. “Honestly, my on-the-job training taught me just as much or more as the classes – and that made studying for and passing them a lot easier,” she added. “Arrowhead has given me so many great opportunities, not only by being able to take classes, but also with such great mentors.”
  • Be real and transparent. “I am not the best, I am not the smartest, I do not have all the answers and I am a fully flawed human being who makes a lot of mistakes,” says Deirdre Gonzalez. “I am, however, strong, confident and have the ability to influence, inspire and motivate people by being vulnerable and authentic. I believe that is why I am trusted with the honor of helping others through leadership.”
  • Pay it forward. “Women, it’s imperative that we support and encourage each other to be authentic and steadfast in our determination to elevate commendable, qualified women into influential roles,” said Becky Pinto. “None of us made it to where we are without the help of others; it’s our turn to mentor and support younger women entering the workforce. They’re bringing new ideas and great technological advancements – let’s embrace them.”
Now it’s your turn: How have you launched yourself out of a career rut, or broken through the glass ceiling? What advice can you share?

Topics: Leadership