How Facing a Challenge at Work Helped Me Advance into a Leadership Role That Didn’t Exist Before

The grass isn’t always greener on the other side — it’s green where you water it. At least that’s what Dana Kleen has found to be true. 

A Director of Sales Development at WP Engine, Kleen says: “If I ever feel that the grass at WP Engine is starting to yellow, I’ll work hard to find a way to bring it back to life. I know the more I invest in the company, the more they will invest in me.”

And that they have. In the four and a half years that she’s worked at WP Engine, Kleen’s needed to step out of her comfort zone, veer off the beaten path and test her limits beyond the imaginable. But she says: “In no way have I been on this journey alone. I have truly felt supported every step of the way.” 

The healthy challenges she experiences at the company, and the hard work required to succeed in her role, have generously contributed to her blossoming career. In one project that required her to manage a struggling team, she “was rewarded with new challenges, a different perspective and exposure to other departments.” And the project, which began as a 3-month commitment, transformed into what is now her full-time leadership role.

We recently spoke to Kleen about what excites her in her current role, what her career development looks like at WP Engine and the best piece of career advice she’s ever received — which helps her stay positive every day.

I’ve been with WP Engine for four and a half years now and I am still amazed that a company like this even exists. I was impressed by the diversity, the number of powerful women in leadership positions and the many awards it’s received such as “Best Places to Work.” 

I quickly realized in my interview that at WP Engine, a “top workplace” does not translate to meaning an “easy workplace,” and I was intrigued. I was craving a new challenge and an exhilarating career that was going to push me to new limits. When I signed the offer letter, I received just that. The journey has been far from easy, but it’s absolutely been worth it.  

Tell me about the roles that you’ve held at your company, as well as your current one. What about this role most excites you? 

I began my career at WP Engine as an individual contributor on the SMB Acquisition Sales team. Within 10 months, I was promoted to Team Lead and then to Manager shortly after. It was motivating to know that most leaders at WP Engine are homegrown and the business truly invests in their employees, looking to promote from our internal talent pool before all else. 

Within the next year, I was asked to help manage our struggling Sales Development team. This role was never part of my “plan,” but I stepped out of my comfort zone and was determined to make an impact. It was supposed to be a 3-month project, but three months has now morphed into two years. I took a risk by veering off the beaten path, but I was rewarded with new challenges, a different perspective and exposure to other departments. 

I was promoted to Senior Manager within a year and then to Director the following year. Celebrating a sales rep advance beyond my team is what excites me the most. It’s very humbling to know I can make a big difference in someone’s life and start their sales career off on the right foot. My personal goal is to get a rep set up for success and promoted within a year.

A lot of people believe that developing your career means changing companies, and not infrequently. What has enabled you to develop/advance your career without job hopping? 

I firmly believe that if you stick around anywhere long enough, opportunity will present itself — and it has. If you like what you do, and you’re good at it, I think you have it made. I don’t need to chase greener grass to find happiness. If I ever feel that the grass at WP Engine is starting to yellow, I’ll work hard to find a way to bring it back to life because I know the more I invest in the company, the more they will invest in me.

Ultimately, what has led you to stay at your company? 

I’ve stayed at WP Engine for the same reason I joined: the challenge. It’s gratifying to know my hard work doesn’t go unnoticed and I am not just a number! The business has continued to believe in me, providing new opportunities and new challenges to stretch me beyond imaginable. And in no way have I been on this journey alone. I have truly felt supported every step of the way.

What was the best quality of the best boss you’ve ever had? 

The best boss I ever had was a relator. He had an ability to form close, honest and trusting relationships with ease. Whether it was an employee of WP Engine, a barista or the dentist down the street, he knew everyone’s personal story. Our one on one meetings were to discuss life, and of course that included business, but our conversations went well beyond that. He helped me through all life milestones (wedding planning, buying a house, preparing for kids, etc.) and I can only hope to offer the same kindness to others. This skill doesn’t come naturally to me and I have to work hard to formulate those deep, personal bonds.

What’s the most memorable piece of career advice you’ve received? 

“Quit taking it personally!” I took a Dale Carnegie leadership course and Q-TIPs (get it?) were on the instructor’s desk. They were flung in the direction of anyone whom showed signs of taking something personally. He emphasized that it’s not about you, and the actions of others are not a reflection of our self-worth. I try to remind myself of this in the toughest of situations, personally and professionally.

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