Pamela Gupta (she/her)

Pamela Gupta (she/her) founded OutSecure, Inc, in 2000 and serves as its CEO. Every 2.5 hours a company is hacked; Ms. Gupta helps companies stay profitable and achieve resilience by identifying key cybersecurity and privacy risk strategy. She is also a member of Women in CyberSecurity (WiCyS).

1. What’s a piece of advice you’ve found especially useful?

In order to bring about systemic cybersecurity change, you have to understand human psychology. Cybersecurity is more than technology; it’s a mindset that involves changing how we think and function.

2. What’s a challenge you’ve faced, and how did you deal with it?

I am a woman entrepreneur in a male-dominated field. Having grown up and done my undergrad in India, I don’t have a strong support network here, which is critical for establishing a successful business.

I deal with it by working harder and smarter. I bootstrapped my company with self-funding, which made marketing more challenging than it already is. One way to market is to speak at events, but if you’re a vendor, you have to pay large sums of money to attend conferences. I didn’t have the resources to pay for presenting, so I devised a solution: given that my firm creates cybersecurity strategy, my client audience is companies in business management. I researched and found that there were no cybersecurity conferences targeted at business professionals and October is National Cybersecurity Awareness Month; so, I took these as an opportunity to start a business-focused cybersecurity conference.

It cost thousands of dollars to rent space, cater, and arrange speakers, so I had to be creative. I reached out to a local university, and after numerous meetings, I was able to convince them to partner with me and provide the venue and food. I then reached out to my network and arranged a whole-day schedule. It was an intense effort, but we held our first CT’s Annual Business Cybersecurity Summit in 2013. I even got a proclamation from the CT Governor declaring the day of the conference as CT’s Cybersecurity Awareness Day! By being agile, I overcame the hurdle of finding speaking (and marketing) opportunities.

3. What’s your favorite book?

The Paper Bag Christmas by Kevin Alan Milne made me laugh and cry.