Accidentally in Love (With Sales)

Like most insurance sales representatives, I’ve dreamed of selling disability insurance my whole life!

OK, you caught me. That’s not exactly true. I was born in the “Insurance Capital of the World” — Hartford, Connecticut — before spending my childhood in Phoenix, Arizona. But the truth is, growing up, I would have never pictured myself in a “sales” position. I pictured “sales” as cold calling, pushy car salesmen, or the person at the mall kiosk who rubs lotion on you as you walk by. Not for me.

Now that I accidentally ended up in a sales position, it turns out my journey may have destined me for sales all along. I just needed to reshape my own mindset of what sales is and meet a few mentors who believed in me along the way.

So how does one end up as a disability insurance wholesaler, anyway? I like to think I learned a little in each job along the way:

  • High school: Grocery story bagger, take out restaurant cashier, nanny, day camp counselor.
  • College: When I originally enrolled at the University of Arizona, I thought about pre-med, teaching, or interior design, but graduating high school in a recession I ultimately settled on the safe choice — a business major in finance. I’m not a “math person” but figured if you’re a people person who can also explain the numbers, you could go far. I also worked in two customer service roles as the cashier at our athlete snack shop and at the student union information desk.
  • Actuarial internship: It was all fun and games until I was required to stare at Microsoft Excel and build financial models all day. Shout-out to our actuaries who make this look easy!
  • Postgraduate: Realizing I wasn’t cut out to be an actuary and with graduation around the corner ,I learned about the power of relationships. My summer nannying position before college was for a family with an amazing mother and woman in business who worked remotely for a great company called Principal. She recommended I apply for a job at Principal, so after graduation I blindly moved to Des Moines, Iowa.
  • The Principal Leadership Development Program (LDP): Principal’s corporate rotational program gave me the opportunity to meet so many amazing people while also figuring out what role might be a good fit for me. I rotated through Corporate Real Estate, our Group Benefits Sales training team, was lent to the United Way through their loaned executive program, spent time in recruiting, and ultimately placed out of the program as an associate account executive for group benefits in Omaha, Nebraska.
  • Group benefits account executive: As an account executive you are the liaison to Principal for broker relationships and their existing clients. These heroes do everything from educating and building broker relationships, solving client problems, retaining clients at a higher premium rate each year, and adding new lines of coverage to a group.

Throughout this journey I realized each of these roles had one thing in common. Whether you’re caring for children, selling the $3 hot dog and chili combo to athletes on game day, recruiting new talent to Principal, or retaining business, life is a game of sales. People will choose to work with people who care, people they like and people who provide great service. It only took 16 years to build up the confidence in myself and take the risk to move to a sales position.

Now I am an individual disability sales manager for Minnesota, the Dakotas and Western Wisconsin. I get to spend every day teaching financial representatives how to have one of the most important conversations they need to have with their clients — the income protection conversation! We get to impact lives when families and business owners need it most, which is a really rewarding career.

So maybe you are:

  • Positive
  • Passionate about our products and services
  • Passionate about helping people
  • Service oriented
  • A good listener
  • Someone who can explain complicated concepts
  • Creative
  • Collaborative
  • Relationship oriented
  • A process improvement specialist
  • A social media brand expert
  • A time management guru
  • A team player

Or maybe you have your own list of unique strengths! Maybe those strengths could make you the next future sales representative? You just don’t know it yet.

There is no right path and no one way to be successful in sales. The best salespeople I know find a way to capitalize on their strengths, stay true to themselves, love to help people and have a lot of fun along the way.

How can you learn more about a career in sales?

  • Join a local Women in Insurance and Financial Services (WIFS) chapter.
  • Join the Women in Sales mentoring program.
  •  Connect with women in sales you know.

Whether you’re a woman in sales like me or have a different experience, I’d love to hear from you. What experiences and which mentors, if any, helped shape your career path? Or if you want to talk about Disability Insurance, I’m always up for that as well!

Courtney Kastelic is Regional Vice President, Individual Disability Income at Principal Financial Group and a member of WIFS' Minnesota Twin Cities Chapter.

Originally posted on WIFS website on March 29, 2023

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