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7 Questions on Leadership with David B. Cross

Name: David B. Cross

Title: SVP and CISO for Oracle SaaS Cloud

Organisation: Oracle and Rain Capital VC

David holds a B.S. in CIS as well as an MBA with a MIS concentration and is a longtime advocate of security application and technology stemming back to his military service when David first started his work in encryption, information protection and analysis of data with his five years’ active-duty service with the aviation electronic warfare community of the United States Navy. David was awarded with numerous honors including a Navy Achievement Medal, Southwest Asia Service Medal, Armed Forces Service Medal and NATO medal for his combat-based tours. David is now the Senior Vice President and Chief Information Security Officer for the Oracle SaaS Cloud Security engineering and operations organization. Previously, David built the public Cloud Security Engineering organization as a Director in the Google Security and Privacy organization for 3 years with his preceding 18 years spent with Microsoft in numerous security platform, cloud, product and engineering leadership roles. David is also a Venture Partner with Rain Capital VC with successful track record with notable acquisitions starting with his seed investment of Twistlock which was acquired by Palo Alto. In addition, David has been a long-time security IP innovator with 30+ patents as well as a contributing author and presenter on many cybersecurity whitepapers, conferences and webinars.

Thank you to the 2,000 leaders who’ve generously done the 7 Questions on Leadership!

I hope David's answers will encourage you in your leadership journey. Enjoy!


Jonno White

1. What have you found most challenging as a leader?

The imposter syndrome is something that will never disappear. Whenever you take on a new position, role, project or leadership opportunity, a natural fear will appear. It is similar to the fear of speaking on stage or in large audiences. It will never disappear, but you can always be prepared and expect what will occur again and again with much more comfort.

2. How did you become a leader? Can you please briefly tell the story?

For myself, I have always been thankful to all the more senior leaders and technology experts that have take the time to help guide, mentor and coach me throughout the years. I believe leadership is about helping others be successful and my responsibility and desire is to provide the same value and experience of guiding, mentoring and coaching to others in the organization who can be more successful and productive as a result.

3. How do you structure your work days from waking up to going to sleep?

Overall, I like to describe my daily as being "work-life choice". It is important to have clear goals individually, as a family and employment. I "choose" and structure every week to have daily goals for physical exercise, family time, critical work activities and individual downtime. I wake up and go to sleep the same time every day. As a military veteran, I have found consistent structure and plans to be very comfortable and help in achieving all my short and long term goals.

4. What's a recent leadership lesson you've learned for the first time or been reminded of?

I am always reminded that the number one priority is "the people". It is not technology, it is not process, it is not knowledge, it is not experience. It is about how you are always bringing people together, how you welcome everyone and how you bring diversity into everything that you do because that will always be the foundation for strong teams.

5. What's one book that has had a profound impact on your leadership so far? Can you please briefly tell the story of how that book impacted your leadership?

It is so hard to choose, but if I had to name one book that has become my personal brand throughout my career it would have to be "Execution: The Discipline of Getting Things Done" by Ram Charan and Larry Bossidy. Every company and organization can have amazing vision or strategy, but in the end it is all about execution. I have continued to extend from my military experience in how I am always focused on completing a mission, accomplishing the target goals and be known as an overall execution expert who "makes things happen".

6. If you could only give one piece of advice to a young leader, what would you say to them?

Never stop learning. Mental fitness and agility comes from continued investment in yourself. It is not about how hard or how many hours you work, it is about how much you invest in yourself. You should never stop investing 4 hours a week in yourself for the rest of your life. Growth, results and opportunities come from learning. Lead by example.

7. What is one meaningful story that comes to mind from your time as a leader, so far?

I will never forget or stop sharing the three best practices one of my first managers shared with me after I transitioned away from my military service:

1. It is not about career ladders, promotion criteria or role checklists - it is about "making things happen". If you continuously make things happen for the company, you will be recognized and rewarded.

2. Whatever you own, do or manage - be the "expert" in the company. Whether it is a project, program, feature, technology or process, be the clear owner and expert that every seeks out for guidance and accountability.

3. The most valuable people in a given company are the people who make others great. Those who contribute and strive for others to be successful are often the most desired and valuable resource in the company.

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