April 18, 2017

One on One with Corey Thomas, CEO of Rapid7: His Career, Leadership Style, & Boston's Thriving Security Cluster

Growing up in a working class family, Corey Thomas was first introduced to the tech industry by his mother. She showed him a computer and quickly, he was inspired by its infinite possibilities.

“Sports and computers both have endless limits, but sports have fixed rules, while computers have no rules,” says Thomas. “I gravitated towards technology for that reason. It was an expansive creative zone for me.”

Thomas went on to study computer science and electrical engineering at Vanderbilt University. He originally started his career in the tech industry by working at AT&T, but it was his time at Deloitte Consulting that was a turning point in his career.

“I became obsessed with the business side of technology,” said Thomas. “I wanted to understand the concepts of how people make decisions, as it dawned on me that the best technologies didn’t always win. People would adopt inferior technology.”

Corey Thomas, Rapid7 CEO
Corey Thomas, President & CEO at Rapid7

After earning his MBA from Harvard Business School, Thomas spent almost 5 years working in Redmond, WA, at Microsoft in a variety of roles. It was at Microsoft where he learned how things worked at scale within different technology ecosystems. He also learned the skill of product management and led one of the largest releases of SQL Server in the company’s history.

At that point, he was interested in doing something new and started talking to companies about CEO opportunities. However, it was a specific reference call which set up the course for his future.

Back in 2008, Rapid7 had roughly 50 employees, about $7M in trailing revenue, and had just received financing from Bain Capital Ventures. Thomas was listed as a reference for its incoming COO, Mike Tuchen. It was during this conversation, when an idea was proposed to Thomas about potentially joining Rapid7 to help build out their operations.

“I was really impressed with Rapid7’s progress to that point and its culture focused on continuous learning,” said Thomas. “But, what really brought me in was how the founders and investors were closely aligned and on the same page.”

The rest, you could say, is history as Thomas worked his way up the ranks at Rapid7 to his current position of CEO. As the leader of a publicly traded tech company in Boston, I was interested in learning more about his leadership style.

Growing up, he didn’t feel like his knowledge around leadership was any different from others, but his appreciation for leadership has grown over time. It has also continued to evolve, as it is very different than what it was even five years ago.

“Some people view leadership as being the captain of the sports team and telling people what to do,” says Thomas. “However, I try to create an environment where people can thrive and achieve greater outcomes.”

A big part of Thomas’ role these days is recruiting and developing talent, as Rapid7 has a promote-from-within mentality. There’s a skills shortage in the security industry and he credits Christina Luconi, Rapid7’s Chief People Officer, as someone who has helped the company accomplish its goals. “The security industry is highly competitive. You need to attract the right talent to compete and the right culture to execute on the company’s vision,” said Thomas.

Not only does Thomas need to think about his leadership style internally, but he also must consider his outward facing style too. As the CEO of a publicly traded company, he states the need  to communicate effectively with customers, investors, partners, etc. “I’ve learned to adapt my leadership style over time,” says Thomas.

Today, Rapid7 has over 800 employees and market cap of over $655M. The security industry is certainly known for its complexity of solutions and five years ago, Rapid7 made a massive investment to make its technology simpler. “The investment has been paying off for our customers,” said Thomas. “We are keeping them protected, while we continue to innovate.”

Another topic that we discussed during our interview was the strength and rapid growth of the security ecosystem in the Boston area. “Most great things form in clusters and the security cluster in Boston is awesome,” said Thomas. “You have Carbon Black that has scaled, Veracode recently sold, and there’s lots of up and coming companies. It’s healthy for all the companies in this cluster.”

Keith Cline is the Founder of VentureFizz.  Follow him on Twitter: @kcline6.​  

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