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Security clashes with cloud: Offensive Security CEO talks cultural mindsets, leadership challenges

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Ning Wang, Offensive Security CEO

Taking on the chief executive position at any company can be a daunting prospect. Every organization has a different culture, processes, and people, and in the world of cybersecurity, board leaders not only have to deal with internal management but also the ever-changing face of threats their customers face.

Offensive Security, known for the development of the Linux Kali penetration testing suite and security certification courses including OSCP Certified Professional, OSEE Exploitation Expert, and the new OSWE Web Expert qualification, became the responsibility of the new CEO Ning Wang three months ago.

Wang’s journey began in China, where she grew up. After studying physics at the University of California, Berkeley, she kickstarted her career at McKinsey & Company before making the shift to startups during the .com bubble, Lynda.com, and finally serving as chief financial officer (CFO) and chief operations officer (COO) of bug bounty platform HackerOne.

The executive then joined Offensive Security, founded in 2000, as its chief executive officer after the cybersecurity firm received a capital investment from Spectrum Equity. 

In an interview with ZDNet, Wang told us that her career has been based on problem-solving, whether practical or business-related, and this is an area of expertise which she has now brought to the table with her latest role at Offensive Security.

One of the first goals, Wang says, is to make sure that communication lines between board levels and general staff are improved and expanded upon, an ongoing trend which the executive has observed during her time in cybersecurity.

“Cybersecurity is no longer just the job of some security director in the company or an afterthought,” Wang says. “In fact, it is on the agenda of the CEO and on the mind of the CEO and board. At HackerOne, a lot of times those initiatives were [issued] directly from the CEO and the board.”

It is not just about making sure executives communicate and drive the company forward by involving staff at all levels — Wang believes that the heart of Offensive Security’s future success is also reliant on the implementation of a “try harder” mindset; not only for employees, but also for the cybersecurity industry and students at large.

Try harder, encourage, and communicate are therefore the recipe ingredients for Wang’s new role.

“When I first started there was a lot of anxiety around all the change that’s going to happen — is the company culture going to vanish? Is the company and the new leader only going to worry about financial numbers and not going to care about the culture and people?,” Wang explained. “But you can’t grow a company, you can’t grow a business, [when] you don’t have people who are really motivated and really are behind your mission.” 

“As a CEO I try to really communicate and listen, and and I don’t have the answers to all the questions but at least I can listen and facilitate more discussions.”

With any change in leadership, however, there will always be resistance to some ideas. In Offensive Security’s case, cloud computing has shown itself to be one such challenge.

See also: FireEye debuts Windows Commando VM as Linux Kali rival

Offensive Security, like many other organizations, relied mainly on in-house applications and systems hooked up to their own data centers. One change that Wang wanted to implement was the increased use of cloud-based services and resources. (There are still some times when on-premise solutions are most suitable than full cloud systems, however.)

“As a security company, this company has — in the past — hardly used any cloud-based tools,” the CEO said. “Any tool we use, whether it’s a conference call system, a ticketing system, or a chat system — it’s all either homegrown or it’s all on-premise where we host the software.”

Given the simplicity, ease of access, and resources available through cloud services such as Salesforce apps or AWS, Wang wanted to bring her new charge up to speed through modern technologies. The idea was originally “met with resistance,” Wang says, but eventually, her team came around to the idea.

TechRepublic: 90% of large tech companies vulnerable to email spoofing

“Initially the idea was, ‘What? no, that’s not how we do things — we are a security company,” Wang explained. “The change is happening and was met with some initial resistance and fear but now people are embracing it.”

Upon taking up the role, Wang says there was not a single full-time sales or marketing employee. Another personal mission was to make sure Offensive Security became well-known not just with practitioners but also the public at large.

In order to do so, the company has increased its focus on advertising and has expanded its range of online certificates including OSWE Web Expert. So far, the feedback has been positive from alumni testing out the new qualification.

CNET: Facial recognition is going to be everywhere

Three months in, there are many changes yet to be made in the organization, with a pivot to the cloud only one of many planned. However, Wang believes that modernization and getting the firm’s name out there is the key to future success. 

“[Linux Kali / OS certifications] are really well-known among the practitioners, whether it is penetration testers or hackers, [but] it is not yet as well-known among the people,” Wang added. “We are a very good brand when it comes to training security people so in order to do that we have to make sure we have the infrastructure in the company to be able to support that growth, and we have to make sure our products will be cutting edge.”

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Phish Fight: Securing Enterprise Communications

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Yes, much of the world may have moved on from email to social media and culturally dubious TikTok dances, yet traditional electronic mail remains a foundation of business communication. And sadly, it remains a prime vector for malware, data leakage, and phishing attacks that can undermine enterprise protections. It doesn’t have to be that way.

In a just released report titled “GigaOm Radar for Phishing Prevention and Detection,” GigaOm Analyst Simon Gibson surveyed more than a dozen enterprise-focused email security solutions. He found a range of approaches to securing communications that often can be fitted together to provide critical, defense-in-depth protection against even determined attackers.

Figure 1. GigaOm Radar for Email Phishing Prevention and Detection

“When evaluating these vendors and their solutions, it is important to consider your own business and workflow,” Gibson writes in the report, stressing the need to deploy solutions that best address your organization’s business workflow and email traffic. “For some it may be preferable to settle on one comprehensive solution, while for others building a best-of-breed architecture from multiple vendors may be preferable.”

In a field of competent solutions, Gibson found that Forcepoint, purchased recently by Raytheon, stood apart thanks to the layered protections provided by its Advanced Classification Engine. Area 1 and Zimperium, meanwhile, are both leaders that exhibit significant momentum, with Area 1 boosted by its recent solution partnership with Virtru, and Zimperium excelling in its deep commitment to mobile message security.

A mobile focus is timely, Gibson says in a video interview for GigaOm. He says companies are “tuning the spigot on” and enabling unprecedented access and reliance on mobile devices, which is creating an urgent need to get ahead of threats.

Gibson’s conclusion in the report? He singles out three things: Defense in depth, awareness of existing patterns and infrastructure, and a healthy respect for the “human factor” that can make security so hard to lock down.

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When Is a DevSecOps Vendor Not a DevSecOps Vendor?

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DevOps’ general aim is to enable a more efficient process for producing software and technology solutions and bringing stakeholders together to speed up delivery. But we know from experience that this inherently creative, outcome-driven approach often forgets about one thing until too late in the process—security. Too often, security is brought into the timeline just before deployment, risking last minute headaches and major delays. The security team is pushed into being the Greek chorus of the process, “ruining everyone’s fun” by demanding changes and slowing things down.

But as we know, in the complex, multi-cloud and containerized environment we find ourselves in, security is becoming more important and challenging than ever. And the costs of security failure are not only measured in slower deployment, but in compliance breaches and reputational damage.

The term “DevSecOps” has been coined to characterize how security needs to be at the heart of the DevOps process. This is in part principle and part tools. As a principle, DevSecOps fits with the concept of “shifting left,” that is, ensuring that security is treated as early as possible in the development process. So far, so simple.

From a tooling perspective, however, things get more complicated, not least because the market has seen a number of platforms marketing themselves as DevSecOps. As we have been writing our Key Criteria report on the subject, we have learned that not all DevSecOps vendors are necessarily DevSecOps vendors. Specifically, we have learned to distinguish capabilities that directly enable the goals of DevSecOps from a process perspective, from those designed to support DevSecOps practices. We could define them as: “Those that do, and those that help.”

This is how to tell the two types of vendor apart and how to use them.

Vendors Enabling DevSecOps: “Tools That Do”

A number of tools work to facilitate the DevSecOps process -– let’s bite the bullet and call them DevSecOps tools. They help teams set out each stage of software development, bringing siloed teams together behind a unified vision that allows fast, high-quality development, with security considerations at its core. DevSecOps tools work across the development process, for example:

  • Create: Help to set and implement policy
  • Develop: Apply guidance to the process and aid its implementation
  • Test: Facilitate and guide security testing procedures
  • Deploy: Provide reports to assure confidence to deploy the application

The key element that sets these tool sets apart is the ability to automate and reduce friction within the development process. They will prompt action, stop a team from moving from one stage to another if the process has not adequately addressed security concerns, and guide the roadmap for the development from start to finish.

Supporting DevSecOps: “Tools That Help”

In this category we place those tools which aid the execution, and monitoring, of good DevSecOps principles. Security scanning and application/infrastructure hardening tools are a key element of these processes: Software composition analysis (SCA) forms a part of the development stage, static/dynamic application security testing (SAST/DAST) is integral to the test stage and runtime app protection (RASP) is a key to the Deploy stage.

Tools like this are a vital part of the security layer of security tooling, especially just before deployment – and they often come with APIs so they can be plugged into the CI/CD process. However, while these capabilities are very important to DevSecOps, they can be seen in more of a supporting role, rather than being DevSecOps tools per se.

DevSecOps-washing is not a good idea for the enterprise

While one might argue that security should never have been shifted right, DevSecOps exists to ensure that security best practices take place across the development lifecycle. A corollary exists to the idea of “tools that help,” namely that organizations implementing these tools are not “doing DevSecOps,” any more than vendors providing these tools are DevSecOps vendors.

The only way to “do” DevSecOps is to fully embrace security at a process management and governance level: This means assessing risk, defining policy, setting review gates, and disallowing progress for insecure deliverables. Organizations that embrace DevSecOps can get help from what we are calling DevSecOps tools, as well as from scanning and hardening tools that help support its goals.

At the end of the day, all security and governance boils down to risk: If you buy a scanning tool so you can check a box that says “DevSecOps,” you are potentially adding to your risk posture, rather than mitigating it. So, get your DevSecOps strategy fixed first, then consider how you can add automation, visibility, and control using “tools that do,” as well as benefit from “tools that help.”

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High Performance Application Security Testing

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This free 1-hour webinar from GigaOm Research. It is hosted by an expert in Application and API testing, and GigaOm analyst, Jake Dolezal. His presentation will focus on the results of high performance testing we completed against two security mechanisms: ModSecurity on NGINX and NGINX App Protect. Additionally, we tested the AWS Web Application Firewall (WAF) as a fully managed security offering.

While performance is important, it is only one criterion for a Web Application Firewall selection. The results of the report are revealing about these platforms. The methodology will be shown with clarity and transparency on how you might replicate these tests to mimic your own workloads and requirements.

Register now to join GigaOm and sponsor NGINX for this free expert webinar.

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