7 Questions with Corey Thomas: President, CEO, Director of Rapid7

Corey E. Thomas

Infinite possibilities drew Corey Thomas, BE ’98, to technology. Infinite curiosity fueled his interest, obsession even, with organizational behavior and the business side of technology. Rapid7, a cybersecurity tech firm based in Boston, has benefited from the combination of the two since 2008, when the founders hired Corey as SVP of marketing and sales. He moved up to COO and, in 2012, CEO, taking the company public in 2015. Previous positions include VP of marketing at Parallels Inc., a visualization technology company; group project manager at Microsoft, launching the worldwide availability of SQL Server and steering product planning for Microsoft’s data platform; and a consultant at Deloitte Consulting. Corey, a member of the Vanderbilt Board of Trust, received a B.E. from Vanderbilt, majoring in electrical engineering and computer science, and an MBA from Harvard Business School. On Feb. 3, 2023, President Joe Biden announced his intent to appoint Corey as one of 14 new members of the President’s National Security Telecommunications Advisory Committee. Corey reads five or six books at a time, a habit he cannot break, and commits to reading two works of fiction for every book of non-fiction. During the pandemic Corey took up archery and learned just how difficult a sport it is—more on that later.

  1. Your early career was focused on figuring out “the recipe” for success. Where did that journey take you? I always wanted to know the best practice for how to be successful in the world. From early on in my career, I assumed there was a single answer to that question and that I could figure it out by learning enough: If I do these things, I will know how to be successful and make it easy. First, I thought it was organizational management and organizational behavior, which led to business school. Then in the first half of my career, I came up with different hypotheses and found career and learning opportunities to test them out: smart people, hardworking people, great strategy, great execution, great culture. But at some point, I learned that there isn’t a definitive recipe and success is a process of discovery, not a state of knowing.
  2. Thinking about your transition from middle to senior management, what was difficult about it? How did you know you were ready?  If you are confident that you are ready, you probably aren’t. You need to have confidence in who you are and what you bring to the table, but temper that with humility and a deep appreciation of all the things you have to learn. When Rapid7’s founders hired me (first as an EVP, then COO), I had expected that if I did a good job, they would back me in my own venture. Rapid7 was founded by serial entrepreneurs, and I had wanted them to support me in starting a company of my own. I was shocked when I got the CEO opportunity, and I was a bit unprepared. I had to be convinced to take it, and I’m thrilled I did.
  3. When it comes to workplace culture, you put a big emphasis on team building and interaction. How do you address the potential perils of “groupthink” against the potential contributions of an individual superstar? Few geniuses can deliver consistently. It does not happen as frequently as you think, and there may be only two or three true geniuses in a generation. We are not the geniuses who are going to get it right across all times and all contexts, so context and the support of a team become incredibly important. As Rapid7 scales out, we want people who have a high degree of self-confidence and humility. People who have high accountability, but a low need to control how exactly they deliver on that commitment with their team. If you think, “I was hired for my expertise in X,” and you expect to come in and just do some X, you are not the right person for us.
  4. How do your best hires demonstrate their intangibles? I want people who are comfortable with messy. Really high quality, good decisions are not necessarily predictable. I tend to seek out unsolved problems and try to solve them, and I am looking for people who have insatiable curiosity. If you are debating an issue you are likely to be uncomfortable a huge percentage of the time. When we are engaging things that matter and don’t know the outcomes, people are uncomfortable in the uncertainty. It should be a good experience, and nobody should be mean in the process, but there should be tension in not knowing and figuring it out. A great team pushes your assumptions about a problem and how to solve it.
  5. You have said you expanded your definition of company culture to include how people, leaders, and the organization behave under stress. How does that play out in the line of fire? I took Edgar Schein’s model of organizational culture and, wanting to be very intentional, focused on behavior under stress. At those times, we should be explorers— collecting data, developing actions, responding, and making adjustments when something doesn’t work. It is during these times of crisis and stress that a leader’s personal behavior is most important because their behavior is scrutinized and adopted by their team— good or bad. Employees understand what is happening, and they want a culture that encourages them to help solve the problem. That’s why under stress we don’t focus on certain aspects of accountability. When the dust settles, yes, talk about why it happened and how to prevent it in the future. But in the moment, you dig in. There’s meaningful, psychological importance to employees seeing that their boss is willing to do the dirtiest jobs to support the team and find creative solutions under stress. We call it “Grabbing a shovel,” and at Rapid7 we even have a rule that no one gets punished in the heart of the battle.
  6. What gives you energy? What do you find relaxing? What gives me energy is long walks, especially in nature. I describe myself as a, “Slow-burn introvert.” I can engage with people for a long time. I do get creative energy from working through a problem by brainstorming and designing with two or three people. I am not very good at relaxing, though I do get some level of relaxation by learning new things. Over the years that has included guitar and martial arts, and during the pandemic I started teaching myself archery. I bought a cheap bow-and-arrow set and watched a lot of YouTube videos. The first time I hit the target—not even the bullseye, just hit the target—three times in a row, I wanted to have a party.
  7. What would you tell one of your children who is a junior in college and stressing out about grades, internships, and social dynamics? I would say, first, never forget that the goal is learning first and foremost and not validation. Validation may be good, but learning is the most important. Second, mistakes, struggles, and screw ups are not personal failings, they’re part of becoming your best self if you learn from them.

*This interview originally appeared in the Spring 2021 issue of Solutions.