Christopher Clai
Senior Director, Information Security (CISO)
Green Thumb
Christopher Clai is the Senior Director, Information Security (CISO) at Green Thumb. He is a results-driven IT professional with over 25 years of experience across multiple industries and IT disciplines with a passion for leveraging governance and technology to drive positive outcomes.
Beyond technical expertise, he has a long history of managing both for-profit and non-profit organizations. He regularly helps organizations develop or build their community stewardship efforts and DE&I initiatives. You may find him as a speaker at various events as he loves to share knowledge and resources to help level up our communities.
A fun fact about Christopher: In the early 2000s, he ran a network of online radio stations which went on for almost a decade.
Learn more about the Chicago CISO community here.
Give us a brief overview of the path that led to your current role.
My journey to my current role has been a culmination of all my experiences coming together. From my early days as a developer and running several businesses, pivoting from various IT responsibilities and roles, to running a Network Operations Center, then a Security Operations Center.
One day, a CISO I was working for helped me realize that the underlying theme in my career had always been Information Security, and he was confident that I could make a positive contribution to the field and industry and encouraged me to specialize. Almost a decade later, here I am, doing exactly that and paying it forward to others.
What is one of your guiding leadership principles?
Resilience. To me, that means being able to change directions, lifting up others, handling adversity, never seeing anything as a permanent obstacle, and standing strong on one’s core principles.
What is the greatest challenge CISOs face today, and how are you addressing it?
Avoiding apathy around security in an organization. It’s all in the messaging, how you support and respond to your end users and your team, and how you partner with the business. Stay positive and supportive, avoid using Fear, Uncertainty, and Doubt, and always find ways to align and be flexible when appropriate and necessary to keep the organization innovative.
What is the key to success for someone just starting out as a CISO?
Learn, live, and contribute positively to the culture of the organization that you serve as it is vital to our ability to run an effective security program, regardless of your scope.
How do you measure success as a leader?
By witnessing and celebrating the growth of those I have led (past and present) and the positive changes I have contributed to my industry, organization, and communities.
What is the value of being a member of Gartner C-level Communities?
For me, the value in being a member is the exchange of ideas and shared challenges that foster a collaborative problem solving environment that can help you bolster your programs.
Gartner C-level Communities Governing Body members share their insights and leadership perspectives to shape the agendas and topics that address the top priorities impacting business leaders today.
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