Rapid7 CEO Corey Thomas

Corey Thomas’ impressive background includes stints at Parallels, Microsoft, AT&T, and Deloitte Consulting as well as degrees from Vanderbilt and Harvard. This experience led him to become CEO of Rapid7 in 2012 and take it public in 2015, with stellar results. As he explained to me, in a world where lack of IT management leads to security compromises, Rapid7 provides the data, visibility, and automation to address it. The company serves more than 7,000 organizations, including over half of the Fortune 100, across 125+ countries.

Like many, including myself, he transitioned from being an engineer to focusing on business/marketing and finally to CEO. I appreciated hearing about the thoughtful way that he approaches the CEO job, especially as a first timer. The self-awareness he demonstrates, which led him to deftly address some challenges early on in the job, is notable. You can read more about this in my latest article for Inc.: 3 Soft Skills CEOs Can’t Ignore

He also brought up an important leadership topic. As I’ve written about before, often throughout our careers we are judged almost solely on our individual contributions. However, when we get to management and leadership positions, we’re evaluated on our ability to build and manage a team. Many aren’t ready for this. This disconnect is why most CEOs, including Corey, value leadership potential so much. Enjoy the interview! 

You got an engineering degree at Vanderbilt. What did you plan to do with it?  

I thought I was going to be a creator and builder of products and technology. I’ve always loved technology and what you could actually do with it. Shortly after I got to college I got my dream internship at AT&T. I discovered that you could have great technical genius, but it is not necessarily correlated with product success. That was startling to me at an early age.

Was there a moment or event that caused you to flip from engineering to business?  

When I was at AT&T (Lucent/Bell Labs era), a company I loved, I got to spend time with some crazy geniuses. In my young mind I could not fathom that they were not the rulers of the world, although you could argue that they were. It was clear that they felt like they were losing ground, of all the people I was aspiring to be. It started the journey of me trying to figure out why technical genius isn’t enough. It quickly morphed into me trying to learn more about the business world. In my last couple of years at school I studied economics along with engineering.

Why did you get your MBA?

AT&T sold my division to IBM. Then I became a consultant at Deloitte Consulting. After working there for two years I went back to get my MBA.

When did the idea hit you that you might be a CEO someday?

It was the tail end when I was at AT&T, leading into becoming a consultant. As I mentioned, I became very interested in leadership and what was happening in business. In the early and mid-90s lots of stuff was going on in the telecom industry, with companies getting bought and sold and startups happening. I was intrigued by the leadership aspects in that period.

You moved into a marketing role for a period of your career. How did that help you as a CEO?

Someone once advised me that you should think about the skills and experiences you are going to wish you had before you got the job. From my background I was comfortable with technology and got pretty good marks for understanding and envisioning it. I knew I needed to understand customers. I definitely needed to wrap my brain around the concept of “just because you build it doesn’t mean people will want it.” Marketing helped me with better understanding customers and their preferences. These pivotal learnings improved my chances of being successful today.

How did you get the CEO role at Rapid7?

I had worked with the prior CEO/founder and the primary investors at the time. I had done a fairly good job at Rapid7, and they were grooming me to be CEO of some venture someday. I just ended up getting the role at the company I had already worked for and knew well.

When you got the CEO job, were there more surprises or differences than you anticipated?

There were not a lot of surprises, but the magnitude of the work was a surprise. When you go from an operational role to being the CEO, you have to put different decision-making processes in place. It takes more time and work to do this transition.

You’ve now had experience going public. I once had a CEO tell me it felt like he had personally gone public. Describe that experience for CEOs.

First, it requires a huge level of transparency. Second, I am a borderline introvert/extrovert. I was brought up that you don’t talk about yourself that much. As a public company CEO you have to provide information and insights about yourself and how you think and operate. I was reluctant at first, but I had to represent the company.

I remember a mentor telling me at the time, “Your job is to educate and promote the company out in the community a lot. If you don’t want to do that then you shouldn’t do this job. If you’re going to do the job you should do it well.” I acknowledged this was right. I now find a way to focus on things like customers and our technology but also do the role as a champion for our employees and customers of the company itself. This was a pretty significant adjustment for me.

How do you think about balancing that? The internal role vs. the public company CEO?

What I think about is my energy and capacity correlated to time, but not perfectly: The number one thing I have to do is understand and act in the interest of our customers. The second thing is to set the culture for the team to provide a great place to work, otherwise it’s all for naught. If you don’t understand customers, you have a hard time building the right culture. The third item is to educate the world on our business and the problems we solve and what we’re doing. I had to let lots of stuff go, such as operations, and do an even better job of delegating. I make sure we have good operations processes in place, but I spend my time on how we think about the values, the culture and the systems of support for our culture and our beliefs.

How do you measure culture? As an engineer I assume you have some way you measure those pieces? 

What I mean by culture is really two things: 1) Are we all moving towards the same destination/direction? Do we have a shared set of assumptions about how we achieve our vision and direction? This is important, because if one group believes we should debate everything out and have tough discussions while another believes in highly collaborative planning with low friction, then you have a mismatch. It’s about having shared assumptions that create success.

2) What I’ve added over time is how do people, leaders, and the organization in general behave under stress? What you see is people say one thing, but when things don’t go well their behavior is different. My job is to reinforce assumptions about how we get there with the right frameworks, processes, and management to ensure our behaviors under stress are consistent with our values.

When it comes to measurement, we do surveys of the entire employee base fairly frequently. We have lots of town hall discussions where we disseminate information and smaller town halls where people share and get feedback. We also do a lot of interviewing of the employee base, both in the moment day-to-day and at regular intervals. We also do exit interviews to get both objective and subjective input.

Do you have any teams outside the U.S. or had M&A activity where you’ve had to integrate new cultures?

The running joke is I’ve never found a smart person I wouldn’t open an office for! Yes we have employees in 50 offices around the world.

Have you found that you have to do things differently from the U.S.?

Yes, we pay close attention to local cultures. But we still have to have a common core. We can’t have different foundational value systems. There are different ways we substantiate that value in different cultures though. My exec team and I spend a lot of time on the road for that reason. There is a fine balance between having a common value system and vision but the proper instantiation for the local context.

How do you find out what’s happening on the ground in your company when you can’t know everyone well?

I set a low threshold for engaging with me. People do so fairly frequently. They have to feel it’s safe and beneficial to engage. I actually try to make it as “cheap” as possible mentally and energetically for them. Also, in every office and group I try to have at least one personal relationship. It’s important to develop relationships with different levels. Every employee should feel comfortable talking to anyone in our organization, including the board. There should be total transparency. Also, I set up a series of one-on-ones when I travel to different offices. Employees are thoughtful about giving feedback. I assume it comes with a lens, but I learn a lot by engaging.

Is there anything you’re seeing that you think other CEOs should follow?

We’re all living in a world and landscape that’s evolving and changing. Because of that the requirements of what people look for in both themselves and their leaders is different. For example, I am valuing less and less people who can process and get to the answers themselves. I value more people who can help groups get through really hard things in ambiguous circumstances. It takes a different set of skills and is a harder way to judge and assess someone. But somebody who can take a group of people and organize them in ambiguous circumstances, even if they got a mediocre outcome, is priceless leadership.