Damian Schenkelman - Principal Architect at Okta, Scaling from Employee 10 to Exit at Auth0

Welcome to Software Snack Bites the Podcast! This podcast will be an exploration of all things enterprise software from technology trend deep dives, to company building, to enterprise purchase decisions.


Damian Schenkelman was Employee 10 at Auth0 and has played multiple roles in the company from early engineer, to first Director of Engineering, to Principal Architect at Okta/Auth0 Lab which is exploring new products in the auth space. He is also an angel investor and advisor to numerous startups and is happy to help any founders who reach out! He joins us today to share the journey of Auth0 from the beginning and how early decisions on things like supporting on-prem and cloud customers can impact a company in the long term. We talk about the differences between being an individual contributor and a manager and also cover topics related to scaling reliability, tradeoffs between microservices & monoliths, and how phase shifts in a company lead to needing to build and codify new decision making frameworks over time. There are numerous insights in here for companies in the early stage and also at scale as to how to avoid potential pitfalls and grow with their customers. For those who don’t know, Auth0 was acquired by Okta for $6.5B in 2020.


Please subscribe directly on Apple Podcasts or Spotify to help support the show!


Where to Find Damian:


LinkedIn:   / damianschenkelman  


Twitter:   / dschenkelman  


Personal Blog: https://yenkel.dev/


Where to Find Shomik:


Twitter:   / shomikghosh21  


LinkedIn:   / shomik-ghosh-a5a71319  


Software Snack Bites Newsletter: https://www.shomik.substack.com


In this episode, we cover:


(00:00) - Damian’s Background


(01:30) - What Auth0 Does & What is Authentication and Authorization


(07:43) - Why Auth0 Focused on Developers from Day One


(10:15) - Signing the First Customers


(14:43) - Tradoffs Between On-Prem and Cloud Customers


(19:06) - Becoming Director of Engineering


(24:05) - Returning Back to Being an Individual Contributor


(27:40) - Leading the Platform Eng Team to Increase Reliability & Scalability


(36:56) - Dealing with Phase Shifts in Auth0 as the Company Scaled


(40:30) - Improving Alignment Between Eng Teams


(44:51) - Working on New Products at Auth0 Lab


(49:20) - Favorite New Technology


(50:43) - Favorite Snack


Additional Show Notes:


Excellent Written Interview about Damian’s Experience: https://staffeng.com/stories/damian-s...


Damian’s Auth0 Podcast Series that Goes Deep into Auth Topics: https://authorizationinsoftware.auth0...


Auth0 Lab’s Twitter:   / auth0lab  


How to Subscribe:


Available on Apple Podcasts (https://podcasts.apple.com/us/podcast...) or Spotify (https://open.spotify.com/show/5voKCX3...) .


This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit shomik.substack.com (https://shomik.substack.com?utm_medium=podcast&utm_campaign=CTA_1)