Unscripted | David Raviv

Mailroom to Cybersecurity Chief: Jason Lewkowicz's Unscripted Journey


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Can starting in the mailroom lead to becoming a top cybersecurity executive?

Join us as Jason Lewkowicz shares his incredible journey from the bottom rung to Chief Services Officer at Optiv, revealing insights that redefine career success in the digital age

In this episode of Unscripted, David Raviv sits down with Jason Lewkowicz, a senior cybersecurity professional at Optiv, to discuss his unconventional career path. Jason shares his story of starting in the mailroom at Anderson Consulting and rising to become

Optiv’s Chief Services Officer. He discusses the evolution of cyber threats, the importance of continuous learning, and the challenges faced by organizations today.

Jason also offers practical advice for those looking to enter the cybersecurity field, emphasizing the importance of perseverance, mentorship, and strategic career planning. This episode is a must-watch for anyone interested in cybersecurity, career growth, and leadership.


00:00 - 02:00: Introduction and Welcome

David introduces Jason Lewkowicz, highlighting his role as a senior cybersecurity professional at Optiv.

02:01 - 07:00: Early Career and Mailroom Experience

Jason shares his journey from starting in the mailroom at Anderson Consulting to moving into IT and cybersecurity.

07:01 - 14:00: Transition to IT and Security

Jason discusses his transition from the mailroom to the IT department, and how he first became interested in cybersecurity during the Melissa virus incident.

14:01 - 20:00: Building a Career in Cybersecurity

Jason explains how he progressed within Accenture, his role in creating the information security program, and the importance of mentorship.

20:01 - 27:00: Challenges and Growth at Cognizant

Jason recounts his experience joining Cognizant as CISO during the Maze breach and the challenges of managing a large-scale incident during the pandemic.

27:01 - 33:00: Moving to Optiv and Strategic Leadership

Jason talks about his move to Optiv, his role in consolidating services, and the importance of operational efficiency and client experience.

33:01 - 40:00: Advice for Aspiring Cybersecurity Professionals

Jason offers advice on how to start a career in cybersecurity, emphasizing the value of project management and incident response roles.

40:01 - 46:00: Importance of Continuous Learning

Jason discusses the need for continuous learning and how staying updated with the latest technologies and trends is crucial in cybersecurity.

46:01 - 53:00: The Role of Communication in Cybersecurity

Jason highlights the importance of effective communication between CIOs and CISOs and how it impacts the success of cybersecurity programs.

53:01 - 59:00: Engaging with Clients and Providing Value

Jason explains how Optiv works with clients to understand their needs, manage expectations, and deliver world-class cybersecurity services.

59:01 - End: Final Thoughts and Contact Information

David and Jason wrap up the discussion, with Jason providing his contact information and encouraging viewers to connect with him on LinkedIn for further insights.

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Unscripted | David RavivBy David Raviv