About SeanSean Kilgore is an Architect at Twilio, where he draws boxes, lighthouses and soapboxes. In Sean’s spare time, he enjoys reading, walking, gaming, and a well-made drink.Links:
Twilio: https://www.twilio.com/

Silvia Botros's Twitter: https://twitter.com/dbsmasher

Sean's Twitter: https://twitter.com/log1kal

TranscriptAnnouncer: Hello, and welcome to Screaming in the Cloud with your host, Chief Cloud Economist at the Duckbill Group, Corey Quinn. This weekly show features conversations with people doing interesting work in the world of cloud, thoughtful commentary on the state of the technical world, and ridiculous titles for which Corey refuses to apologize. This is Screaming in the Cloud.Corey: Your company might be stuck in the middle of a DevOps revolution without even realizing it. Lucky you! Does your company culture discourage risk? Are you willing to admit it? Does your team have clear responsibilities? Depends on who you ask. Are you struggling to get buy in on DevOps practices? Well, download the 2021 State of DevOps report brought to you annually by Puppet since 2011 to explore the trends and blockers keeping evolution firms stuck in the middle of their DevOps evolution. Because they fail to evolve or die like dinosaurs. The significance of organizational buy in, and oh it is significant indeed, and why team identities and interaction models matter. Not to mention weither the use of automation and the cloud translate to DevOps success. All that and more awaits you. Visit: www.puppet.com to download your copy of the report now!Corey: Up next we’ve got the latest hits from Veem. Its climbing charts everywhere and soon its going to climb right into your heart. Here it is!Corey: Welcome to Screaming in the Cloud. I’m Corey Quinn. I’m joined this week by Sean Kilgore who’s an architect at a small company called Twilio. Sean, welcome to the show.Sean: Corey, it’s a pleasure to be here.Corey: It really is. You’re one of those fun people that I always mean to catch up with and really do a deep dive in, but we keep passing like ships in the night. And in fact, I want to go back to more or less what is pretty damn close to your first real job in technology. You were a network administrator at Lutheran High School in Orange, California.Sean: I was.Corey: And at that same time, I was a network administrator down the street at Chapman University, also in Orange, California. And despite that, we have traveled in many of the same circles since, but we have never met in person despite copious opportunities to do so.Sean: That is amazing.Corey: Talking to you is like looking into a funhouse mirror of what would it have been like if I could, you know, hold down a job, and was actually good at things. It’s really fun. Apparently, I’d be able to grow a better beard.Sean: I don’t know about that. My beard is pretty patchy.Corey: Yeah, I look like an angry 14-year-old trying to prove a point to Mommy and Daddy. But that’s not really the direction that we need to take this in today. And you’ve done a lot of stuff that aligns with things that are near and dear to my heart. For the last—what is it now?—six years and change? Seven years and change? You’ve been at SendGrid, then Twilio through acquisition?Sean: Mm-hm.Corey: And you have done basically every operations-looking job at that company. You’ve had a bunch of titles. You wound up going from DevOps engineer to a team lead, then to a senior DevOps engineer again, and you call—you voluntarily move back to an individual contributor role. Let’s start there. What was management like?Sean: The management was interesting. My first go at that, I had no idea what I was doing, and so I didn’t know how to ask for the help that I needed. And so my wife and I refer to that time as the time that I played a lot of video games. Just, I wasn’t prepared for the emotional outlay that managing humans costs. And so I would end up spending my nights just playing video games trying to unwind and un