This is the Way: Kaylee Chappelow of RiskGenius

December 8, 2020

Kaylee Chappelow of RiskGenius has always been, as her friends say, obsessed with growth.

As a high school student growing up in Blue Springs, a Kansas City suburb, Kaylee was an over-achiever. Along with participation in numerous extra-curricular activities, she graduated high school fourth in her class with more than 44 hours of college credit. This allowed her to finish her degree in sales and marketing from Missouri State University in only three years.

Throughout her young adult life, Kaylee has had a focus on helping people. She wants to help other people who are focused on growth to achieve their goals, which is why she currently serves as the Missouri DECA State Director of Leadership. (DECA is a 6,000-member, co-curricular business, and marketing organization for high school students.)

Kaylee first opened the door to the insurance industry in college, when she interned at Croley Insurance as a licensed navigator. She walked people through the website and helped them enroll in health insurance. She loved how this industry can help people and wanted to be a broker at a bigger scale, so she interned next at Lockton Companies.

After two and a half years at Lockton, Kaylee was offered a position at start-up RiskGenius. The name felt prophetic appropriate to Kaylee because, at the time, she felt she was taking a risk to leave a good job at Lockton for a start-up insurtech company. She trusted her gut and accepted the position.

What might have felt like a risk before, now is a no-brainer. Kaylee feels she was born to work in sales at a start-up. She loves the entrepreneurial experience, and it fits her like a glove because she loves embracing new challenges. The most recent opportunity to continue her passion for growth came in October of this year when Bold Penguin acquired RiskGenius.

“The chance to grow with Bold Penguin and sell their newly released agency terminal product is really exciting to me.”

This is the way Kaylee Chappelow works.



  1. Location:

Kansas City, Missouri - Live on the Plaza.

  1. Current gig:

Manager of Business Development (sales) at RiskGenius. My company was recently acquired by Bold Penguin.

  1. One word that describes how you like to work:


  1. Current mobile device:

iPhone X (already feel like it is outdated).

  1. Current computer:

MacBook Pro.

  1. Project(s) you’re currently working on:

Closing out a couple of sales opportunities for 2020 and building my pipeline for 2021. Helping with the integration of Bold Penguin in terms of improving our sales processes and leveraging resources, it has been really fun to get to know the new team and work together to help our current and overlapping clients.

  1. Accomplishments you’re proud of:

Proving my value and what I brought to the table to be put in a sales role. They were looking for someone more experienced. I had to show that I had the grit and drive to work extremely hard, was dedicated to learning and open to feedback, and had the people and critical thinking skills necessary to succeed in the role.

  1. What are your goals for the next 12 months?

My goals are to get more comfortable with the sales process, help implement our software at several p&c insurance companies who have a need to understand the language that exists in their policies and be more confident in my role and execution. I would also like to finish 21 books in 2021 and continue to get to know myself, and have personal growth, particularly around patience and listening.

  1. What are your biggest professional challenges?

Working independently because sales is all about experience, and there is a lot I have not seen or navigated, sometimes I can be quick to want others’ opinions instead of trusting my instincts. Every insurance company operates differently in terms of how they partner with vendors, so it is a challenge to get to know each organization and their internal processes.

  1. What do you like most about your job?

I LOVE that I really create my own opportunity and can see the direct impact I am having on our start-up. It is really fulfilling.

  1. What technology, apps, or tools can’t you live without?

Hmmm, Grammarly/spell check is huge for me. It is an app that corrects spelling because I am the WORST speller ever. Google snoozes are huge. I like that I can set an email to re-pop back into my mailbox. It keeps me organized and timely on my follow-ups. Slack is huge for collaboration, and obviously, with all that is going on, Zoom has been pivotal to keep meeting with my clients and prospects.

  1. Describe your workspace.

Well, right now it is at home, so I have my MacBook, my extra monitor, a picture of my best friends, a sign that says “Boss Babe,” Never split the difference is a book that sits on my desk, I reference it often. I have some positive quotes I have heard or read on sticky notes/in a spiral notecard book. One says, “be relentless.” Another says, “it is the union between belief and action that brings about a life of integrity.”

  1. How do you manage your to-do list?

I set intentions and my tasks at the end of the day for the next day. I start with the hardest or tasks I am looking forward to doing the least. I set meetings if I need to update someone on a project first, so I create a deadline for myself from the get-go.

  1. What’s your best time-saving tip or hack?

I actually got this from our current COO, but scheduling meetings, scheduling them back to back as a block rather than doing one 30-minute meeting in the morning and another two hours later. The idea is that you want to create blocks of time that do not include meetings so you can focus and get things done, rather than having 30-minute windows to work on tasks in between meetings because, by the time you really get into a groove, you have to stop and hop to another meeting.

  1. What’s the first thing you do when you get in the office?

Since I work from home now, I get to my desk at 7:30 and go through my spiral notecard book of inspiring quotes and bible verses to start the day off in a positive way, then I read the Morning Brew, it is a quick newsletter that covers high level what is going on in the world - political, sports, pop-culture, stock markets, tech. 

  1. What do you listen to while working?

I listen to music - Taylor Swift, Drake, Maverick City Music, Justin Bieber. I love podcasts, but I cannot focus on work and listen to them simultaneously.

  1. What are you currently reading?

Invisible Man - by Ralph Ellison. It addresses the social and intellectual issues faced by African American people in the early 1900s and frankly are still facing today. Also going through the book of Jonah with my small group at church, supplemented by the Prodigal’s Prophet by Timothy Keller.


  1. Coffee or tea?

Coffee - has to be decaf though because I am caffeine sensitive.

  1. Night owl or morning person?

Night owl that forces herself to be a morning person.

  1. What are you watching on Netflix right now?

Sister Sister is my background show if I am cleaning or answering emails at night. The past few nights I have been watching the new Netflix Christmas movies like Midnight at Magnolia and Operation Christmas Drop. Netflix Christmas movies never disappoint.

  1. What does a typical day look like for you?

Wake up, get some water, spend time reading/going through my spiral notecard book, work, eat lunch - typically a vegetable power bowl, work, do a workout class, and on to whatever evening activity I have - time with friends, small group, volunteer, or watch a show with a glass of wine and a home-cooked meal.

  1. Who are your business idols and why?

Jeremy Smith - President and COO of RiskGenius - he is honest, fair, and makes people feel valued. Plus, he is so positive and doesn’t spell ill of anyone. Sheryl Sandberg, COO of Facebook. She wrote Lean In, one of my favorite books, and is setting the stage for women in business. Brene Brown - she focuses on vulnerability and being transparent, which is so vital.

  1. What’s the best advice you’ve ever received?

Work hard as if no one is looking. My mom taught me that, and it is true that if you work hard with integrity, you will be successful in what you do.

  1. If you could switch jobs with someone, who would it be?

I would switch jobs with my friend, a nurse, to see what it is like because her stories are always wild, but I would need to magically not be queasy at the sight of blood.

  1. Who would you like to see in a future This is the Way post?

Chris Cheatham.


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