C-suite career advice: Ashish Gupta, Bugcrowd

What advice would you give to someone starting their career in IT? “To be successful in IT, you must possess a passion for technology and understand that not everyone is a technologist.”


Name: Ashish Gupta

Company: Bugcrowd

Job Title: CEO and President

Location: San Francisco

Ashish Gupta brings more than 25 years of general management experience and has had leadership roles in marketing, sales, business development and products. Prior to Bugcrowd, Gupta was Infoblox’s EVP and Chief Marketing Officer responsible for worldwide strategy and operations for global corporate and product marketing, including brand awareness, go-to-market programs, and demand generation initiatives. Gupta specialises in creating new markets and categories, positioning companies for growth, and developing differentiated business strategies in highly competitive industries. He has held leadership positions with other venture-backed and publicly traded technology companies, including Microsoft, Actian (acquired by HCL), Telera (acquired by Alcatel/Genesys), Vidyo (acquired by EngHouse), Deloitte Consulting and Hewlett-Packard.  

What was the most valuable piece of career advice that you received? The most valuable piece of advice I received was to build up a network of mentors as they can be a great source of situational advice, terrific confidants, and unbiased providers of feedback.  

One of my mentors once shared a quote from General Douglas MacArthur: “The history of failure in war, or in any other human endeavor, can almost be summed up in two words: Too late.” Those two words now have a profound impact on everything we do at Bugcrowd. It is an important reminder to carefully consider both speed and direction as you work to build momentum and critical mass. It also means you do not need to wait to get the perfect solution. Instead, focus on A/B testing to avoid being too late.  

What was the worst piece of business advice that you received? Someone once told me to always hire the smartest person you can find. While there is a lot of merit to getting the person with high intellectual horsepower, it is incredibly important to ensure the person is also a cultural fit and has the emotional horsepower for the role. When you combine these three qualities, you ensure the employee has the kind of grit and approach that leads to long term success.  

I have seen firsthand that the best employees have a combination of IQ, EQ, and grit. So, while this person told me to find the most intellectually sound person, the reality is that you need the emotional component to be a well-rounded and effective employee. 

What advice would you give to someone starting their career in IT? To be successful in IT, you must possess a passion for technology and understand that not everyone is a technologist. You need to be able to help people grasp how technology can make business processes easier and ensure better business outcomes. Be solution-oriented to make your internal or external customers successful in everything you do! 

Did you always want to work in IT? I wanted to start a car company when I was growing up in India. However, my outlook changed when I came to the U.S. to attend college and was introduced to computers for the first time. I became passionate about technology enablement and helping businesses understand how it can contribute to productivity in a way that is so powerful that it transforms processes, people, and socio-economic environments. I particularly love the intersection where technology transforms existing businesses and markets by creating operational inflection points.

What was your first job in IT? My first real job was within the IT organisation at Hewlett Packard. Interestingly, I came from a liberal arts background. Coming from liberal arts and working in IT at a highly technical company really allowed me to practice how technology can solve business challenges. It was here that I merged my passion for technology with my ability to write and communicate effectively to ensure the adoption of the technologies we were sponsoring. It was a fantastic learning experience for me under a great leader who taught me how to make technology understandable for the everyday person.  

What are some common misconceptions about working in IT? When I started, there was a common misconception that everyone ate a lot of peanut butter with M&Ms and drank a lot of Jolt cola. The other common misconception was that you had to be a technologist to be successful in IT, which is not true. My first boss was a history major with a keen ability to relate how technology can help make the world work better, which made her super successful at HP and an incredible mentor for me.  

What tips would you give to someone aiming for a c-level position? I would say that thinking about your career from a near-, mid- and long-term perspective is essential. It’s like taking a long putt in golf. Unless you are Tiger Woods, you break the 40-foot putt into a few shorter putts that get you to the ultimate goal. At the same time, it is important to learn from every experience, from every turn in the path, and find people who can provide real-time advice. Take the opportunity to learn everything you can because regardless of whether you are going for a C-level position or not, it’s essential to have a core understanding of how people, technology, processes and markets work so you can bring together a cross-functional group of people to drive success.  

What are your career ambitions, and have you reached them yet? I am continuing to aspire to new things. Remaining ambitious is important, and it is also crucial to routinely reevaluate the goals you have based on your experiences.  

As a mountaineer, I relate ambitions to an experience I had when climbing Mount Rainier.  After a full night of climbing through dangerous rock overhangs, snowfields and scree, you reach a point called Disappointment Cleaver. It’s called that because when you reach it, you are generally exhausted after a grueling climb.  It is a great achievement, but when you turn the corner, you see the rest of Mount Rainier ahead of you.  

Similarly, your achievements will lead you to even higher aspirations and serve as a springboard for the next, and possibly bigger, ambition. Keep learning, keep growing and your ambitions can be limitless.  

Do you have a good work/life balance in your current role? It depends on who you ask. Work/life balance has a very personal aspect to it that stems from the passion and the mission that someone is going after. Sometimes work becomes part of your life because you are so passionate about it. At that point, work-life and personal life start to blend to enable you to achieve your goals. I will say that it is vital to have a support system around you and not take it for granted. I have the benefit of having my wife and kids believe in what I do wholeheartedly. At the same time, it is my responsibility to disconnect and create meaningful experiences with them as well.

What, if anything, would you change about the route your career path has taken?  I would love to have taken a more direct route. If I had the chance to seek out mentors earlier, I would have been able to understand the ramifications of certain decisions faster. I came to America with one suitcase and intended to go back to India in four years after I finished college. Luckily, I was able to stay here and benefit from the system's abundant resources and openness which allowed me to learn on the job and collect experiences that have shaped me as a person.  

A great example of the impact of mentors in my life occurred during my time at HP. Our professional services team's general manager told me that I had done a fair amount in technology, and it was time for me to understand how business works more formally. He went so far as to introduce me to UCLA’s Anderson School of Business, where I ended up going for my MBA. The experience and learnings from my fellow students, who came from all walks of life, and my professors on real-life business topics was eye-opening for me. It also created an important pivot in my career from pure technology to a more hybrid tech-enabled business path.   

Which would you recommend: A coding bootcamp or a computer science degree? It really depends on where someone is in their career and learning cycle. There are definite advantages to both. In a boot-camp, the learnings will generally be pointed and topical, the opportunity cost may be lower, and by self-selecting on individual boot-camps, there could be a good fit for the person to match the content to their interests and inclinations. A computer science degree is great for someone who wants to build a foundation and get the tools required to evolve their knowledge faster with the evolution of technology. While taking the time to get a degree might feel like a large investment, it is a decision that can be balanced fairly easily between opportunity costs versus the long-run benefits of having a broad base of fundamentals. Net net, I don’t think you can go wrong if you plan and prioritise your learning curriculum in a way that suits you.  

How important are specific certifications? Certifications give you credibility within the community and can be bolstered with real-life experience in applying the learnings. The goal should be to solve problems and perform actions that make things better with the knowledge gained in a variety of modes. Our community is an excellent example of this. People can find vulnerabilities for customers even without a computer science degree or a certification. It comes down to what you are doing with that certification from a learning and credibility standpoint.  

What are the three skills or abilities you look for in prospective candidates? I believe in EIEIO, which stands for energy, intelligence, experience, integrity, and organisational fit.  

Energy, intelligence, and experience tie back to a person's IQ side, while integrity and organisational fit make up the EQ side. As I said before, you need to factor in both sides of a person to find the right candidate.  

What would put you off a candidate? What puts me off is someone who does not seem sincere. I like people who try to understand why they want to interview with us and can give insight into what about our company drives them to want to join. I also love it when candidates can provide SAR examples, which is another acronym I like that stands for situational, actions and results.  

What are the most common mistakes made by candidates in an interview? How can those mistakes be avoided?  Not coming prepared with knowledge about the company and not writing a thank you email are two common mistakes. 

Being a management consultant in the past, I am used to putting everything into 2x2 matrices to predict a candidate's performance and prevent hiring mistakes. Doing so allows me to examine the qualities of people I hired and did not hire to determine if a new candidate shows the potential for success in the role.  

You do not want to leave an interview having been placed in either of the “negative” quadrants within the matrix that show you are not a fit for the position or that you left the interview without the person understanding your talents fully.  

Candidates should also come prepared with questions and use some of the interview time to ensure the company is the right fit for their goals and aspirations.  

Do you think it is better to have technical or business skills – or a mix of both? It’s important to have both skills to be an effective leader. You need a deep understanding of the technology, its value to customers and the market opportunity. Equally important is an understanding of the operations, financial and people side of the business.