Employee Q&A: Kelly Stapleton, Director of Sales

by Cristina Merrill

Kelly Stapleton doesn’t back down from a challenge. Guerrero’s director of sales, who also leads our Tier 3 content and advertising managers, grew up with three older brothers and spent her childhood playing competitive sports. She joined Guerrero’s ranks straight after college and worked full time while completing her master’s degree. More than four years after she joined us, she’s still got that fire. 

Where are you originally from and what is your background? 

I am from Downers Grove, Illinois. I have three older brothers: a twin brother who is nine minutes older, as well as two other brothers who are three and four years older. I would have to say being the youngest of four and the only female truly instilled a competitive nature in me that still stands today. Name a sport, I’ve probably played it, and I always had to be the best at it. I’ve played on men’s soccer and hockey teams (but mostly in women’s leagues), and any challenge that’s sent my way is one I’m prepared to overcome. At one point, I had the dream of being on the United States women’s national soccer team, wanting to be the next Mia Hamm, but figured third place in state back in high school was enough for my soccer career!

I did undergrad at DePaul University, where I got my bachelor’s degree in public relations and advertising with a minor in graphic design. I then received my MA in organizational and relational communication studies, also from DePaul. I completed my bachelor’s and master’s degrees in five-and-a-half years!

How did you first come to work for Guerrero? 

I started at Guerrero right out of undergrad in 2017, while still going to night class three days a week for my master’s degree. I started off as a content and advertising manager, completed my master’s, and was promoted to organizational effectiveness specialist, which allowed me to strategically partner with the sales leadership team to drive initiatives and outcomes for the sales floor.

What do you do at Guerrero today? 

Currently, I am a director of sales, leading Tier 3. The individuals on my team come directly out of onboarding and tend to be the “greenest” from a sales skill set and performance perspective. As such, I build out new workshops regularly and facilitate these development opportunities biweekly and even monthly, depending on current needs.

How would you describe your leadership style? 

I would have to say my leadership style is evolving. I aim to be a servant leader but find that phrase tends to mean something different based on who you’re speaking with, so let me explain.

My main focus is to be the expert resource and leader who removes obstacles and challenges that are keeping my team members from doing their jobs productively on a day-to-day basis and providing opportunities of professional development to my team members. This includes helping them find leads to reach out to, creating a new development workshop, implementing process changes and script adjustments, listening to calls and providing immediate feedback, fostering collaboration within the team to spark new perspectives, and more.

I work to create safe spaces that encourage vulnerability followed by growth for my people. Additionally, work and life are no longer two separate entities. Balance is key and it’s looking to be more fluid than we have ever thought and seen before. The pandemic is a great reflection of this conclusion.

With that in mind, I also take on the responsibility to ensure that my people are supported both at work and personally. I don’t care if you’re not working for two hours because a family member is sick. What I care more about is the family member that’s sick and how I can support the employee while they’re out of pocket.

How have you maintained a connection with your team during the pandemic? 

There’s power in using technology, especially in a remote world. Slack, daily phone conversations, weekly one-one-one meetings, and team meetings over Zoom have been the main platforms and methods that I’ve been using to stay engaged with my people and for my people to stay engaged with each other. I encourage transparent communication now more than ever as it allows flexibility and accommodation to be had when necessary. My team also does team and individual incentives, and we aim to celebrate any and all wins here.

How has Guerrero evolved over the years? What’s the most marked difference from when you started? 

I would say that our culture and product offerings have evolved most since starting here in 2017. Most recently, the pandemic has truly supported this evolution to its fullest. Our digital offerings have become more valuable now than ever. From virtual events to creating motion graphic-based covers for each of our issues to new websites for our brands, our content and offerings have been dramatically enhanced over the past few years! Additionally, the collaboration within teams and just professional relationships in general have grown more than ever expected while remote as we all had to create and navigate a new normal together.

What makes Guerrero such a great place to work?  

The people. Ever since starting here, it was obvious that the people culture here was unique from other corporate environments. Everyone knows each other, and the collaboration here is awesome. There’s a sense of freedom when it comes to being able to see an idea through to fruition and develop professionally in your own ways here. In the sales department especially, collaboration across sellers is expected and embraced, there’s no wrong question to ask here. Everyone is willing to share their best practices, templates, etc. with newer sellers to help them succeed in their role.

What do you like to do when you are not working?

In my free time, I’m either reading a book, enjoying the outside, or, if I have the time, painting and making art. Most of the artwork hanging up in my apartment was actually made by me and it’s just something I like to do whenever I have the free time to do so. Acrylic paint is my go-to.

What else would you like to share about yourself?

I’m also a really big plant person. I’ve got about ten different plant babies I care for on the regular and I somehow am always buying a new plant when the opportunity arises!