How to Thwart Terrorist Attacks and Help Save Countless Lives, with Jay Kaplan, CEO and Co-Founder of Synack

Jay started his career at the NSA and brought his love of uncovering cyber vulnerabilities to the private sector through Synack. In this interview, Jay gives his perspective on how to find product-market fit in cyber security, how early customers shape the product, and how to balance the sales and leadership responsibilities of being a CEO.

Jay Kaplan is the CEO and Co-Founder of Synack, the hacker-powered security platform for the enterprise. Prior to founding Synack, Jay served in a number of cyber-related positions at the Department of Defense and NSA, as a member of the DoD’s Incident Response and Red Team and as a Senior Computer Network Exploitation and Vulnerability Analyst at the National Security Agency. He received multiple accolades for classified work conducted while at the NSA, where his focus was supporting counterterrorism-related intelligence operations. Jay was a former member of the Commission on Cyber Security for the 44th President. He received a BS in Computer Science with a focus on Information Assurance and a MS in Engineering Management from George Washington University while studying under a DoD/NSA-sponsored fellowship.

Highlights from the episode: 4:02 How do you go from the NSA to building a hacking company? 6:21 How did you find your cofounder? 9:33 How did you find product-market fit? 11:03 How did you launch your go-to-market strategy and break into a new geography? 13:01 Why did you choose to launch your business in SF? 13:45 How did you win your first customers? 16:33 How did early customers change what you are building? Did you change certain things you weren’t expecting to in those early days? 17:46 How have you thought about building your team and what’s important when you’re hiring somebody new? What’s worked well for you and what are some pitfalls to avoid? 20:27 How do you balance the job of selling the product with the other responsibilities of being a CEO? 22:05 When building your team, how did you decide it was the right time to bring on execs? 24:07 How did you generate demand around a new product? 26:35 What’s the worst moment you’ve had in a meeting? 27:55 Tell us about your hiring philosophy 29:18 What’s the best thing you’ve done to maintain the spirit and culture of your company? 30:59 What is the best book that you’ve read recently?