Our Lead(H)er series features impressive women leaders in the Tech Industry. In this Q&A, we are featuring Cindy Stanton, VP, VRM Practice Leader at Rapid7.
Where did you grow up and how would you describe yourself as a child?
I grew up outside of Boston in Boxford, MA with my parents and my younger sister. I was quite curious as a child and always interested in nature. I would collect a bucket of seashells and then study what had lived in each shell, creating shoebox displays with my view on how they should be classified.
I wanted to try almost anything in my youth. I enjoyed playing sports (both individual and team), playing musical instruments (the flute, oboe, and piano), and participating in school activities (plays, every academic team, German club, and an environmental club). I think that my propensity to stay busy and being part of teams are traits that have stayed with me throughout my life and career.
What did you study in college and what was your first job out of school?
At Dartmouth College, I studied biology modified with environmental science. And I continued my penchant for being engaged outside the classroom. I served as Vice President of my sorority and captain of the college’s rugby team. I also worked in a local start-up bookstore. At that job, we started a business creating copyright-approved packets that professors wanted their students to read (i.e., articles) beyond the textbooks that we stocked. It was an amazing experience. I was involved in creating an expo for other businesses that wanted to access the student market during our back to school rush and designed a database and workflows to support our business processes. That taste of entrepreneurship influenced me greatly. Indeed, it shifted my path from medical school to business. I participated in on-campus recruiting and took my first post-college job as an account rep for a paper mill. You know the television show “The Office”? We sold to companies like Dunder Mifflin. I was told by several people that I would never regret the sales experience. They were correct. It was extremely beneficial and fascinating to meet the needs of different types of companies ranging from a school that needed copy paper to the retail company trying to minimize shipping costs for catalogs to the largest publishers in New York City. There was also a bit of a wow factor working on deals that would take fifty truckloads to deliver.
Can you share the details on your career path and what were the critical moments that got you to where you are today?
I never viewed my career path as having definitive milestones and/or a linear progression. Rather, I have always looked for a team of people I can enjoy and learn from and a challenge that I find interesting.
One obvious key moment in my career was switching from a paper mill to an Internet start-up focused on the paper industry. At its core, this was a move from manufacturing to technology (where I have stayed ever since). With respect to the security industry—where I have spent almost twenty years—it was more luck than long-term planning. I took a job in security initially, because it would give me some time in London, while I applied to graduate school. Instead I found that I really loved the security space and have since been able to partner with all sorts of companies to help them protect their businesses.
I would say most of my critical moments were the result of managers believing in me and trusting me to take on more projects and responsibility. When I have lost track of that truth, I have made decisions to work in situations that did not necessarily propel me forward and in fact were detrimental. It is something I have promised myself to be mindful of going forward.
What is your current role and responsibilities?
I am responsible for the Vulnerability Risk Management Practice at Rapid7, which includes our vulnerability management, application security, and offensive security products and services. Rapid7 is structured into practices that are devoted to focusing on particular customer problems in the security space. By bringing together product management, user experience, engineering, product marketing, and team members that help us map back to key cross-practice functions like Sales Engineering and Support, we are able to be highly focused on our customers getting the most value out of the solutions in each practice area. In my role, I am responsible for our products and services meeting our promises to customers and working with my team to set our roadmap and plans to continue to evolve and delight our customers. I have an amazing team, and it is a real delight to work with them, as we set ambitious goals to improve the way customers consume our products and strive to meet them.
Looking back, is this where you thought you’d be professionally? Was it always your goal to be in this position?
A person can only foresee so far into the future. Cybersecurity was not on my radar, when I was in college and applying for jobs. Once I did find this market I enjoyed, I have looked for ways to explore new facets like moving to a company focused on securing Public Cloud, because I wanted to understand how that IT trend was going to impact my area. Some of my decisions worked out, some were not as positive. However, I am so grateful for all of those experiences. I certainly am happy where I am today and am excited about what the future may bring.
For people who are looking to be in a similar position, what advice would you give to others in terms of helping them achieve their career goals?
My advice would be to look for opportunities to work cross-functionally to solve problems. I have spent most of my career in product management, which is grounded in understanding customer problems and working across teams to help solve them. It is of critical importance to develop deep partnerships within your organization to deliver results. I sought out a product management role out of graduate school to gain that perspective, and I found much satisfaction in those roles.
I would also advise being open to taking customer facing roles that are opportunities for impact. These roles can help build perspective invaluable to developing the right solution and working with your peers to get that solution to customers. And being open to opportunities to drive impact that are outside your comfort zone is always a plus. Be comfortable taking risks and be okay with admitting when those risks have not delivered your desired result, so you can change your course and get in a better situation. Broad experiences and perspectives provide the experience to tackle a cross-functional role like the one I enjoy.
What are the most important skills that you need to do your job well?
I think the most important skills for my job are systems thinking, being data driven, and having empathy. System thinking allows me to look at each part of our work to build and market our products and think about how it impacts the overall customer experience. Then using data to understand those experiences, solve problems, and develop the right metrics to track our progress is critical to how we stay on track and help influence others to support our mission. And I don’t think I can overstate how crucial empathy is to helping not only to understand what our customers need from us to get value and meet their needs, but also to be better partners internally to drive a cohesive approach across all functions to support progress for customers.
What do you find most interesting/rewarding about your work? What’s most challenging?
What intrigued me about cybersecurity from the start was the need to evolve to meet the changing threats from human adversaries. Over time, it has become clear that easy to use and effective solutions are the best deterrents to the majority of threats. I have worked with many customers on the bleeding edge of technology and security, but at this stage in my career I am also really passionate about solving security problems for companies with fewer resources and skills. Often, we are working with customers as they navigate their worst day. Helping them respond, separate the initial fears from the reality of impact and supporting them as they plan to evolve to mitigate the threat in the future is really rewarding.
The challenge that I like to tackle is making navigating the complex world of cybersecurity simpler for our customers. Making security more attainable to every organization is a passion of mine and an exciting challenge to take on.
What is your proudest professional accomplishment?
I am proud of a number of moments in my career. One that was early on, but always stays with me is working to find a new home for my team, when my first cybersecurity company in London lost funding, due to a conflict with investors rather than health of the business. I am proud of staying focused in that turbulent time to build the case to be successfully acquired by a US based cybersecurity firm. Our office’s success following the acquisition allowed us to quickly become 25% of overall revenue, responsible for bringing in the top commercial clients and supporting that firm’s acquisition by a large telecom. Our team of wickedly smart penetration testers, experienced security consultants and sharp sales people came to work everyday believing we could slay dragons, and somehow we did. I am proud of our accomplishments and also the friendships that I still cherish today.
Are you involved with any professional organizations outside of the company? Volunteer work?
I genuinely do wish that I were involved in professional organizations, but there are only so many hours in a day. I do attend local events for women’s technology and product groups. I have two elementary school aged daughters and a 16-year-old stepson. I find myself thinking about life as seasons, and this is a season where my commitment to my children and our community has taken precedence over professional organizations. I am a board member of my children’s PTA, lead my oldest daughter’s girl scout troop, and manage my daughter’s sports teams (my husband serves as the coach). I am also involved in community service programs through our church.
What’s next for you and your career?
I have been at Rapid7 for almost a year. When I joined Rapid7, I felt like I was coming home. I love the culture, the people and the problems we are solving for customers. Hopefully, what is next in my career is to continue to contribute to our mission in a way that maximizes my impact for our team and my customers. I know it sounds corny, but when you find a place that lets you be your best, you want to just stay there and do just that.
Q&A
What do you enjoy doing in your free time?
Free time is such a lovely idea! I wish there were more of it! In my free time, I love to spend time with my family. Whether playing or watching sports (we live very close to a college, where we are big fans of their teams), walking in the woods, or just cuddling and watching a movie, they really are the focus of my free time these days.
How do you manage stress?
I should say exercise, and I have found particularly during the last month here at home, it has been a big help. I try to stay focused on all the things that I am grateful for. During the Coronavirus, I still have plenty of work to do. But there is no group of people I would rather be on lockdown with than my family.
I think for me the greatest stress relief is connecting with others. Before the lockdown, one of my best friends and I would connect for 15 minutes in the morning on our commutes. I also have friends from my children's school that share the frustrations and help see the funny side of things. Sharing my worries, helping someone else with theirs and trying to find humor in this crazy journey we are all on is something that helps me to manage my stress.
How many cups of coffee do you have in a day?
Zero. I am one of those strange people that does not drink coffee. Everyone told me it would happen in college, first job, living in Europe, graduate school, first baby, and I just never liked the taste. I have a terrible habit of grabbing a Coke Zero in the mid-afternoon for a little jolt. If you see me in the morning, please excuse my uncaffienated self.
What's one of your favorite places in the Boston area?
I grew up in Boston and one of the things I have loved about joining Rapid7 is getting back to Boston regularly. Spending time in Boxford at my parents’ house with my kids is probably my favorite thing. Having two little city kids from DC getting to roam the woods and enjoy lots of space to play has brought me a lot of joy.
Any book or podcast recommendations?
I do not read nearly as much as I did when I was younger. But I do listen to podcasts, while commuting and exercising. My favorite podcasts are SaaStr, Darknet Diaries, and Armchair Expert with Dax Shepherd.
What advice do you have for recent college graduates?
Every role in a company is important. Being a great team member is about not only your skill and hard work, but about how you work to make everyone on the team better and meet your shared goals. Trust that a focus on being part of and contributing to a great team will deliver opportunity. And remember that careers are long. You are not in a race and oftentimes your progression is not linear, so be patient and maximize where you are versus always looking to what is next.
