Failing Upwards: How to Rise in Cybersecurity by finding (and exploiting) your weaknesses

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Presented at BSidesLV 2023 by

Wes Sheppard

One day as an sysadmin I was asked to just deal with the WAF one day and now I’m a CSO, 18,000 miles, 5 countries and 6 years later. How did this happen?! Full disclosure: I’m a mediocre sysadmin, an okay engineer, an acceptable architect, and a reasonably good infosec officer. What links them, and my rise through the corporate layers, is that at one point or another my hard work hit a wall and they said “you know what? You’ve done well but how about you head upward while the more apt people finish what you started?” So here I am, rising far too quickly, doing just enough to keep the Imposter Syndrome at bay, and somehow succeeding at (cybersec) business without really trying. Come find out how!