Leadership Lab

Leadership Q&A with Corey Thomas, CEO, Rapid 7

Leadership Q&A is a monthly series that shares insight from leaders within Boston's startup community. This month, we spoke to Corey Thomas, Chief Executive Officer of Rapid 7.

INTELLIGENT.LY: What was your first job?

Corey: My very first job started when I was 12 and was the assistant janitor at a set of local churches in our community. I began my career in the tech industry working for AT&T, but it was my time at Deloitte Consulting that served as a turning point in my career. I initially gravitated towards this field as I recognized that computers have endless limits, and no rules, and this passion has carried throughout the entirety of my career.

INTELLIGENT.LY: Share some of your hidden talents?

Corey: I play the ukulele with my son, although I’m not very good at it, as well as the guitar. “Twinkle, Twinkle, Little Star” is our hit duet. I’m also a self-proclaimed Cards Against Humanity shark — my dark sense of humor is always big help.

INTELLIGENT.LY:  What are you most excited about in the Boston tech space?

Corey: It’s been really fun to watch the cyber-security ecosystem evolve here in Boston. Most great things form in clusters, and the growing security talent and expertise in Boston is remarkable. We’ve seen multiple, global security incidents in the past few weeks, and it has been an eye-opening sequence of events not only for individuals, but for organizations who are recognizing the need for better protection. Security organizations are popping up all over the map and Boston has become a hub for many of these emerging tech companies.

INTELLIGENT.LY:  Talk to us about the importance of mentors and coaches in your professional life. How did these relationships begin?

Corey: Whether it was old bosses or family members, there’s a few people in my life I credit a lot of my successes to. My mentors constantly challenged me as I progressed through the growing pains of management and various roles, asking me to truly think about whether or not I’d make a good CEO and leader. When asking, they didn’t want me to reflect on this from a selfish perspective for instance, whether I could handle the responsibilities, finances, things of that nature. Instead, they were referring to whether I could lead a company and hold the responsibility of hundreds of employees depending and trusting on me to move the company forward in a positive way. It’s a tough question to be asked at such a young age, but nobody said this was going to be an easy journey.

INTELLIGENT.LY:  What is the best leadership advice you ever received?

Corey: When I was beginning my career, I was extremely aggressive and wanted to advance at a very rapid pace (no pun intended). My boss at the time sat me down and said, “you’re going to get where you’re going; the question is, do you want to be good when you get there, or do you just want to get there fast”? I’m like, “of course I want to get there fast, and I want to be good.” He responded, “alright, in what ways can getting there fast make you not good when you get there?” That was a huge point in my development process that put things in perspective for me.

INTELLIGENT.LY:  What’s the most essential function of your job as a leader?

Corey: Honestly, one of the most crucial functions lies within recruiting and developing talent. How can you have a strong company if it’s not fortified with premier talent from the ground up? There’s a skills shortage in the security industry, as it’s a highly-competitive market, and adding key people to your company is a never-ending search. Finding the perfect balance between employees that allow us to compete in a saturated market and those that embody the company culture we foster here at Rapid7 is the ultimate goal.

INTELLIGENT.LY: If you could talk to your past self, when you first became a people leader, what advice would you give yourself?

Corey: Give everyone a chance for their moment in the spotlight. The littlest person at any company could end up having the biggest impact on any given day. You never know someone’s potential unless you give them the opportunity to live up to it.

INTELLIGENT.LY:  What advice would you give to first time managers?

Corey: Surround yourself with talent that does the job better than you. The biggest component to a successful company is every employee working together in a seamless manner towards one overarching goal. Alignment is exhausting work because it requires turning friction and discord into creativity and commitment. But this is the essential work of managers and leaders. Especially within small startups, if there’s one chink in the armor, it can be detrimental towards the growth and success of your organization.

INTELLIGENT.LY:  What was the hardest lesson you had to learn as a manager/leader?

Corey: I used to believe that the right thing was simple but I discovered that for many decisions the right thing is contextual. Right for which set of people in which timeframe. For example, when do you let individuals or teams struggle as part of their learning and when do you jump in to help and support. It’s easy say focus on the long term but frequently that means lots of pain in the short term for people that you care about. Big moral decisions are with a clear right and wrong are easy, it’s the everyday decisions that require judgement that are much harder than expected, especially when you are operating in multiple timeframes at once. Am I making decisions based on past experience, am I making decisions focused on what’s happening now, or am I am making decisions based on future impact. All are right and relevant but that requires judgement.