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

Presented at BSidesLV 2023, Aug. 8, 2023, 10:30 a.m. (45 minutes).

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!

Presenters:

  • Wes Sheppard
    Hello there! I'm Wes, and I come from a lot of places. From America to China to Japan to Europe, and from IT to Engineering to Butt to InfoSec, it's been a wild ride with stories to spare! My career focuses have been in Butt Security and Infrastructure-level Security, which over time has migrated to Cyber Risk, Data Privacy, and Cybersecurity Law. The best part of this field is how you can take a side hustle or interest and just roll it into your career (^_^) These days I'm a CIO in Canada whilst also being a regular contributor to BSides & Defcon, a data privacy advocate and frequent learner-of-things. If I can help open the door or guide a path, please reach out!

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