CISO, Skyline Technology Solutions

Ira Winkler

While Ira Winkler’s tenure as CISO within Skyline Technology Solutions has been short, he has made a significant impact. In October 2020, he took over a newly established security department, grown organically out of a successful network and IT services operations.

He implemented formal processes for the performance of security functions and has matured the program significantly. He standardized training and certification requirements for the team and established a vision for career progression for people wanting to pursue cybersecurity as a career.

His efforts have had a significant impact on the security of Skyline as well as its customers, and have resulted in streamlined operations within the organization as a whole. He has worked to standardize proposals, which allows for more seamless back office functions, while simplifying the work of the sales and delivery teams.

“When I arrived at Skyline, there was a very talented team that did not have their work established as repeatable processes. While the efforts are still in progress, many processes are now specifically defined with playbooks. This allows work to not only be more efficient, it provides Skyline’s customers with services that best meet their needs. Additionally, there are career paths being defined. This allows for increased employee satisfaction, which in turn provides for reduced turnover, which itself results in more consistent service to clients,” he says.

Winkler has more than three decades of information security experiences and has worked with law enforcement, performing the first studies on Information Warfare for the Pentagon, among other iconic work. He began his career at the National Security Agency, where he served in various roles as an Intelligence and Computer Systems Analyst. After leaving government service, he went on to serve as President of the Internet Security Advisors Group, Chief Security Strategist at HP Consulting, and Director of Technology of the National Computer Security Association. He was also on the Graduate and Undergraduate faculties of the Johns Hopkins University and the University of Maryland.

The project he is most proud of is when he was brought in by the CISO of a Global 5 company, who was frustrated with the lack of support he was receiving from his CEO. “The [CISO] had previously brought in the Big 4 firms to perform penetration tests, which all showed the corporate network and systems to be vulnerable. For lack of a better term, they couldn’t make a business case for improved cybersecurity efforts,” Winkler explains. “He brought me in, and as opposed to proving the networks vulnerable, I performed an espionage simulation and within three days provided the CISO with information ‘stolen’ that is worth billions of dollars to the company. The CISO took the findings to the CEO. The next week, the cybersecurity budget was increased by more than $10,000,000, and they hired CISOs for each business unit of the company. Not only did the company drastically improve its security posture, there are more than a dozen people who have established careers as a result of my work.”

Winkler is also author of six books, including “Spies Among Us” and “Advanced Persistent Security” — both of which were named to the Cybersecurity Canon Hall of Fame — and the bestseller “Through the Eyes of the Enemy.” He has won a Hall of Fame award from the Information Systems Security Association, as well as several other prestigious industry awards.