Interview with Jeremiah Grossman, CTO of WhiteHat Security
by Mirko Zorz - Monday, 24 September 2007.
Lessons Learned:
  • IDS says everyone is attacking you with everything they got all the time.
  • A hacker, who just has to find a single vulnerability, has it easier than a security professional, who has to defend against all vulnerabilities all the time.
  • Everyone with a website gets a “vulnerability assessment,” probably several per day. Whether you pay for the results or not is another matter.
  • Use security obscurity to your advantage.
  • Security solutions that work for smaller websites don’t necessarily scale for the larger ones.
This year you've been selected as one of the Top 25 CTO's according to InfoWorld. How does it feel to have your work recognized and being put head to head with other well known industry giants?

It’s an honor. “Surreal” is the best word I can use to describe being listed next to names from top companies like VeriSign, 3Com, Motorola, and Credit Suisse. And while I’m receiving a lot of the credit recently, which I appreciate, it’s really the result of years of tireless effort from many amazing people at WhiteHat Security and around the webappsec community. I was always fond of the quote by Sir Isaac Newton, “If I have been able to see further, it was only because I stood on the shoulders of giants.”

Has the award put a spotlight on WhiteHat Security?

It’s funny, I was just getting used to seeing our name in the press about every week or so, then this happened. Now it’s almost every day we’re mentioned and it’s actually been difficult for us to keep up with all the inbound interest in WhiteHat Sentinel. Part of the build up is of course press generated. But, most of the increase is simply due to the complexity and difficulty of Web application security and the need for easy-to-use vulnerability management services. We’re really excited about the future and we seem to be at the right spot at the right time.

With the constant evolution of threats, what kind of technology challenges does WhiteHat Security face?

It’s interesting. It’s not so much the new attacks or techniques that keep us on our toes, but the adoption of new Web development technologies such as Ajax, Flash, Java, etc. Websites using these technologies are really no more or less secure. But, what is more difficult is scanning for the vulnerabilities within them. Today’s Web pages share more similarities with running applications instead of traditional HTML documents. This makes “crawling” the website that much harder. By extension, the attack surface is more difficult to define, and as a result black box “fuzzing” is constantly challenged.

In your opinion, how has the Web security scene evolved in the last few years?

It might sound odd, but one big difference for me is that only a few years ago people barely knew that “Web application security” existed or that firewalls and SSL didn’t protect a website. Today, almost everyone I talk to, from coast to coast and country to country, has that figured out. Now everyone wants to know what the latest trends and best practices are. The other big difference is the availability of knowledge. Before, the information people needed to secure a website really wasn’t documented. Now, people have access to websites with hundreds of white papers, presentations, and books right at their fingertips. If you want to secure a website, the information to do so is out there.

Have new development techniques brought more problems?

Some experts like to say that Ajax or Web 2.0 is the harbinger of new attacks. I’m not one of them. Fundamentally, we’re dealing with the same problems in the same locations. The challenges that Ajax brings land more on the security vendor than on the enterprise. We have to find vulnerabilities in these custom Web applications and Ajax-enabled applications are much more difficult to do so. Read any of Network Computing’s scanner product reviews and you’ll see what I mean.

What are the security tools/services that you use on a daily basis and couldn't live without?

I’ve blogged about the speed hack contests we hold at the office. This is where we race to find the first and the best vulnerability in a never-before-seen-website. For speed, nothing beats Firefox, the Web Developer Toolbar, and having the Paros or Burp proxy handy. If I happen to get stuck on an XSS filter, call up RSnake’s XSS cheat sheet, use the encoders at the bottom, and that usually does the trick.

If I woke up tomorrow back at Yahoo!, or was responsible for the security of any website, (I know I’m biased here) the honest answer is I’d get the Sentinel Service deployed immediately. The service is easy and complete, but most of all a security professional’s time is precious. Sure they could do the vulnerability assessment work themselves with each site update, but it’s a poor use of their time and expertise. Their time and expertise is better spent focusing on strategic solutions and big picture thinking, rather than trying to identify, prioritize and weeding through the next hundred Cross-Site Scripting, SQL Injection, or whatever other vulnerabilities there might be.


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