C-suite career advice: Chris DeRamus, Rapid7

What are the three skills or abilities you look for in prospective candidates?  "A prospective candidate must have a deep passion for technology."

DivvyCloud by Rapid7

Name: Chris DeRamus

Company: DivvyCloud by Rapid7

Job Title: VP of Technology, Cloud Security Practice

Location: Arlington, Virginia

Chris DeRamus is Rapid7's VP of Technology, Cloud Security Practice, where he leads the engineering teams while driving new innovation. He is a technical pioneer whose passion is finding innovative and elegant new ways to deliver security, compliance and governance to customers running at scale in hybrid cloud environments. He remains deeply technical, writing code, and diving into the latest technologies and services being deployed by partners like Amazon, Microsoft, Google, VMware, and OpenStack. Previously, DeRamus was the co-founder and CTO of DivvyCloud before the company’s acquisition by Rapid7 in May 2020.

What was the most valuable piece of career advice that you received? The most valuable piece of career advice that I have received is to continuously work both harder and smarter in one’s professional role. In my experience, in order for an employee to solidify themselves as a central figure of high value to a company, they must showcase intelligent results and work twice as hard as others. As an example, early on in my career, I would devote 60-70 hours of work per week to advance in my career. Acknowledging that perseverance is equal to aspiration is crucial and will empower one to ascend up the career ladder at an accelerated pace.

It is also important to understand that passion is critical for success and for personal fulfillment. I made the decision to enter the workforce right out of high school instead of taking the traditional route and attending college straight away. This forced me to find my passion early on, motivating me to continue to increase my IT knowledge and make new discoveries, all while working harder than any of my counterparts, in order to gain credibility. 

What was the worst piece of business advice that you received? Shortly after founding DivvyCloud, one of the first investors we met with expressed much doubt over our business model. The investor advised us to pivot our focus specifically to AWS services rather than a multi-cloud approach.

However, we stuck with our gut, even in the face of adversity. Now, 89% of organisations have or plan to adopt a multi-cloud approach. From early on, we trusted our instincts that multi-cloud environments would rapidly become a highly common and highly complex undertaking for businesses. The complexity and frequency of the problem has ultimately reaffirmed our multi-cloud strategy and elevated our product’s value.

This interaction taught me to trust my instincts and my experience. This also reinforced my practice of focusing on the bigger picture and solving for challenges 5-10 plus years out – not just the immediate issues at hand. 

What advice would you give to someone starting their career in IT/tech? For someone starting their career in the technology sector, it is crucial that they are cognizant of the ever-increasing rate of change of technology environment and are able to embrace a constant stream of new challenges. Massive shifts in IT happen every day, and tech and security professionals must constantly refresh their skill set and become experts on new trends. Different types of cybersecurity threats and attack vectors are continuously emerging, and one’s security strategy must evolve to stay ahead of malicious actors.

With this in mind, one should look for extracurricular opportunities within their focus areas to strengthen their knowledge beyond just their daily tasks. For example, during my first career role, I was responsible for manually managing remote access. However, I was aware of different, innovative ways to complete this task more efficiently. I presented a new system for remote access management, and my employer embraced it.

By keeping an open mind, challenging your knowledge set, and never accepting the status quo of your role, you can set yourself apart from others.

Did you always want to work in IT/tech? I knew very early on that technology was my passion. From the first time I played a video game, I was certain I wanted to work with computers. Every spare moment was spent on computers. In high school, I began reconfiguring my own computers and attending local networking parties to learn more about networking, security, computing, and ethernet. At such networking events, not only was I exposed to the task of fixing and tweaking systems, I also had the opportunity to build and maintain networks of 1,000s of computers. This experience was an accelerator for my career, exposing me to technology that I wouldn't have been able to be hands-on with until college. However, it was not until my experience with DivvyCloud that I began to focus more on programming. 

What was your first job in IT/tech? My first job in the technology industry was at a temp-agency, ManPower. I spent 90 days as a contractor at SAIC as a remote access administrator before being offered a full-time position. This was not the “IT job” I had imagined and was very process-heavy and focused on data entry. Thus, I focused on finding ways to automate manual processes, so that I was able to explore additional job functions by spending less time on data entry which in turn also benefited the company. This allowed me to showcase to my employer that I was capable of going beyond what was asked of me and that I was devoted to amplifying my role.

Overall, my career path was anything but traditional. It was not until after working for three years in the field that I decided to go to college and get a degree while still working remotely. Even though this was not a standard path, it proved to be successful in my case, and I believe that anyone interested in a technological career should choose a path that works for them, even if it is more untraditional.

What are some common misconceptions about working in IT/tech? One of the most common misconceptions is that a career in technology comes with a low chance of promotions and that the only way to move up is to move to another company. Because there is not a clear structure of moving up, it is crucial that one stands out and proves themselves useful to the company even beyond their responsibilities and the specific role for which they were hired. 

When working in the technology space, do not succumb to the assumption that there is little room for promotion. Instead, be loyal to your employer and keep growing with them. Furthermore, do not believe that you are effectively forced and compartmentalised to only work on specific assigned tasks. Take a step further and find ways to be beneficial to the employer outside of your explicit duties. Showcasing how your skills can benefit an employer in more ways can drive career acceleration, because an employer will become more willing to consider different career paths as a result.

What tips would you give to someone aiming for a c-level position? For anyone aiming for a c-level position, they must have a broad set of knowledge and skills. A c-level executive does not have to be the absolute best of a specific focus area, yet it is critical that they have knowledge around business concepts and understand how technology, innovations, and investments strategically move a company forward over time. As an example, one does not have to be the best engineer to become a Chief Technology Office, but they must understand the business and be a customer-minded individual. Every successful organisation is customer-first in its mission and mindset and always does what is best in the eyes of the customer.

Additionally, a C-level executive must have the ability to work well with others and lead by example. One must embrace and promote professional debate, and not confuse productive or challenging conversations with conflict. The best business decisions come from collaboration and at times, debate. As an executive, it is important to create a culture where people feel comfortable with challenging one another for the better – at all levels, if it is a technological or a business matter. No employee should be too afraid to ask the manager questions.

Furthermore, if someone is aiming for a c-level position, it is important that they showcase that they are not afraid to get into the trenches and work alongside lower level employees and collaborate directly with the team. One must understand that they are only as good as the team of people that they lead.

What are your career ambitions and have you reached them yet? A huge ambition of mine is to rapidly grow a successful startup in its first year: to develop a great idea, build a company, receive the capital to make it successful and grow, and have the end result be a successful exit. 

I am very fortunate to say that the dream of co-founding a successful startup and leading it through to acquisition has now been met. DivvyCloud was acquired by Rapid7 in May 2020. With this acquisition, DivvyCloud is now able to expand worldwide and given the nature of Rapid7’s pre-existing relationships, DivvyCloud can build in new ways and more quickly. I am excited that I reached this goal and am able to provide our customers the most complete, best-in-class cloud security platform available and drive even greater innovation in cloud security.

Thus far, I have reached many of my career ambitions, but I will always have further aspirations beyond my work at DivvyCloud and I am thrilled to see what the future has in store.

Do you have a good work life balance in your current role? Unfortunately, it is very difficult for me to have a healthy work-life balance. Given that I am hyper-sensitive to customer growth and success as well as loss, it can be difficult to shut off the “work” side of myself.

However, when you are passionate about your work, happiness is evident. I am a big believer in the old saying, “if you love what you do, you’ll never work a day in your life.” One must always remain passionate about the opportunity to work in their role and for their employer. Work should not be accomplished solely for the reward of a paycheck. It is crucial that one wakes up excited to work – that is what it all boils down to. 

What, if anything, would you change about the route your career path has taken? Since I worked for the public sector very early on in my career, I often had to work with outdated, old technology. This environment temporarily halted my exploration of new technologies and innovative trends in the industry. If I had joined the private sector earlier, I believe it would have accelerated my career. 

My first job in technology within the private sector allowed me to experiment with new technology and taught me how to do so much more with less, increasing productivity and efficiency. Time for research and development is crucial for innovation and any company should allot 10-15 percent of time for this. Focusing on a career path that allows for an evolving skill set in technology will result in success.

Which would you recommend: A coding bootcamp or a computer science degree? I would recommend a computer information systems degree over a computer science degree and over coding bootcamp. A computer science degree is hyper-focused and is not as broad as a computer information systems degree. The technology stack is vast and encompasses much more than just writing code. Thus, a degree should provide a broad set of skills and fundamental knowledge across multiple areas of technology. Thereafter, bootcamps and certifications can be useful as an add-on, providing further depth to one’s curriculum and can help build a more focused skill set for a particular career route.

Overall, it’s important to note that education must be coupled with real life experience. Getting involved with ambitious entrepreneurs in the field and working alongside technologists at a successful startup is the best education. 

How important are specific certifications? Certifications in the cloud computing industry are increasingly important and are becoming a necessity. For someone starting a career in IT, certifications can help get a foot in the door. Hyper-focused certifications that hone in on relevant skills that an employer is seeking right away can be extremely useful for an employer and increase an employee’s value to the company.

Additionally, because of the rate of change in the IT landscape, it’s also important to continue education and seek new certifications over time to remain relevant in the field and desirable to employers.

What are the three skills or abilities you look for in prospective candidates? A prospective candidate must have a deep passion for technology. A candidate should be able to differentiate themselves and prove how their passion for technology shapes their everyday life, even outside of work. Being receptive to problem solving, having an open mind, and showcasing intellectual curiosity helps reveal one’s passion for technology to an employer. Specifically, intellectual curiosity is a key trait. It should be clear that a prospective candidate is curious about the industry and is devoted to expanding their knowledge set. Devotion to solving a problem and understanding the root of the issue is crucial, and no candidate should portray that they only are interested in seeking the fastest answer.

Also, a candidate must enjoy working with others in a team setting, and look forward to collaboration.

1 2 Page 1
Page 1 of 2