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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.

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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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Cloud Data Security

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Data security has become an immutable part of the technology stack for modern applications. Protecting application assets and data against cybercriminal activities, insider threats, and basic human negligence is no longer an afterthought. It must be addressed early and often, both in the application development cycle and the data analytics stack.

The requirements have grown well beyond the simplistic features provided by data platforms, and as a result a competitive industry has emerged to address the security layer. The capabilities of this layer must be more than thorough, they must also be usable and streamlined, adding a minimum of overhead to existing processes.

To measure the policy management burden, we designed a reproducible test that included a standardized, publicly available dataset and a number of access control policy management scenarios based on real world use cases we have observed for cloud data workloads. We tested two options: Apache Ranger with Apache Atlas and Immuta. This study contrasts the differences between a largely role-based access control model with object tagging (OT-RBAC) to a pure attribute-based access control (ABAC) model using these respective technologies.

This study captures the time and effort involved in managing the ever-evolving access control policies at a modern data-driven enterprise. With this study, we show the impacts of data access control policy management in terms of:

  • Dynamic versus static
  • Scalability
  • Evolvability

In our scenarios, Ranger alone took 76x more policy changes than Immuta to accomplish the same data security objectives, while Ranger with Apache Atlas took 63x more policy changes. For our advanced use cases, Immuta only required one policy change each, while Ranger was not able to fulfill the data security requirement at all.

This study exposed the limitations of extending legacy Hadoop security components into cloud use cases. Apache Ranger uses static policies in an OT-RBAC model for the Hadoop ecosystem with very limited support for attributes. The difference between it and Immuta’s attribute-based access control model (ABAC) became clear. By leveraging dynamic variables, nested attributes, and global row-level policies and row-level security, Immuta can be quickly implemented and updated in comparison with Ranger.

Using Ranger as a data security mechanism creates a high policy-management burden compared to Immuta, as organizations migrate and expand cloud data use—which is shown here to provide scalability, clarity, and evolvability in a complex enterprise’s data security and governance needs.

The chart in Figure 1 reveals the difference in cumulative policy changes required for each platform configuration.

Figure 1. Difference in Cumulative Policy Changes

The assessment and scoring rubric and methodology is detailed in the report. We leave the issue of fairness for the reader to determine. We strongly encourage you, as the reader, to discern for yourself what is of value. We hope this report is informative and helpful in uncovering some of the challenges and nuances of data governance platform selection. You are encouraged to compile your own representative use cases and workflows and review these platforms in a way that is applicable to your requirements.

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GigaOm Radar for Data Loss Prevention

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Data is at the core of modern business: It is our intellectual property, the lifeblood of our interactions with our employees, partners, and customers, and a true business asset. But in a world of increasingly distributed workforces, a growing threat from cybercriminals and bad actors, and ever more stringent regulation, our data is at risk and the impact of losing it, or losing access to it, can be catastrophic.

With this in mind, ensuring a strong data management and security strategy must be high on the agenda of any modern enterprise. Security of our data has to be a primary concern. Ensuring we know how, why, and where our data is used is crucial, as is the need to be sure that data does not leave the organization without appropriate checks and balances.

Keeping ahead of this challenge and mitigating the risk requires a multi-faceted approach. People and processes are key, as, of course, is technology in any data loss prevention (DLP) strategy.

This has led to a reevaluation of both technology and approach to DLP; a recognition that we must evolve an approach that is holistic, intelligent, and able to apply context to our data usage. DLP must form part of a broader risk management strategy.

Within this report, we evaluate the leading vendors who are offering solutions that can form part of your DLP strategy—tools that understand data as well as evaluate insider risk to help mitigate the threat of data loss. This report aims to give enterprise decision-makers an overview of how these offerings can be a part of a wider data security approach.

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Key Criteria for Evaluating Data Loss Prevention Platforms

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Data is a crucial asset for modern businesses and has to be protected in the same way as any other corporate asset, with diligence and care. Loss of data can have catastrophic effects, from reputational damage to significant fines for breaking increasingly stringent regulations.

While the risk of data loss is not new, the landscape we operate in is evolving rapidly. Data can leave data centers in many ways, whether accidental or malicious. The routes for exfiltration also continue to grow, ranging from email, USB sticks, and laptops to ever-more-widely-adopted cloud applications, collaboration tools, and mobile devices. This is driving a resurgence in the enterprise’s need to ensure that no data leaves the organization without appropriate checks and balances in place.

Keeping ahead of this challenge and mitigating the risk requires a multi-faceted approach. Policy, people, and technology are critical components in a data loss prevention (DLP) strategy.

As with any information security strategy, technology plays a significant role. DLP technology has traditionally played a part in helping organizations to mitigate some of the risks of uncontrolled data exfiltration. However, both the technology and threat landscape have shifted significantly, which has led to a reevaluation of DLP tools and strategy.

The modern approach to the challenge needs to be holistic and intelligent, capable of applying context to data usage by building a broader understanding of what the data is, who is using it, and why. Systems in place must also be able to learn when user activity should be classified as unusual so they can better interpret signs of a potential breach.

This advanced approach is also driving new ways of defining the discipline of data loss prevention. Dealing with these risks cannot be viewed in isolation; rather, it must be part of a wider insider risk-management strategy.

Stopping the loss of data, accidental or otherwise, is no small task. This GigaOM Key Criteria Report details DLP solutions and identifies key criteria and evaluation metrics for selecting such a solution. The corresponding GigOm Radar Report identifies vendors and products in this sector that excel. Together, these reports will give decision-makers an overview of the market to help them evaluate existing platforms and decide where to invest.

How to Read this Report

This GigaOm report is one of a series of documents that helps IT organizations assess competing solutions in the context of well-defined features and criteria. For a fuller understanding consider reviewing the following reports:

Key Criteria report: A detailed market sector analysis that assesses the impact that key product features and criteria have on top-line solution characteristics—such as scalability, performance, and TCO—that drive purchase decisions.

GigaOm Radar report: A forward-looking analysis that plots the relative value and progression of vendor solutions along multiple axes based on strategy and execution. The Radar report includes a breakdown of each vendor’s offering in the sector.

Solution Profile: An in-depth vendor analysis that builds on the framework developed in the Key Criteria and Radar reports to assess a company’s engagement within a technology sector. This analysis includes forward-looking guidance around both strategy and product.

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