Published on 26 April 2012 by

This week I took on the role of CTO at Puppet Labs, and started reflecting on the awesome journey that led me here.

It was 2006, and I was scrambling to make it onto the last bus back to San Francisco from the Apple WWDC Beer Bash down in Cupertino. I'd been to quite a few Beer Bashes and knew the drill: forget the lineup for the campus store, just concentrate on finding beer and the few Apple employees who could fix the OpenDirectory bugs that were making my life hell. Both objectives were completed, leaving me only minutes to avoid having to spend way too much money getting a taxi back up to the city.

Fatefully, I found a seat next to this intensely opinionated sysadmin, Jeff McCune (later to become one of the first pro services guys at Puppet Labs, and now one of our core developers). He recognized me from my WWDC presentation that year and started grilling me about how I ran my university campus, particularly the file-based configuration management system I used, Radmind, and the hacked up framework I'd put in place to try to manage higher level objects than mere files.

He'd been to a talk by Luke Kanies (now the CEO of Puppet Labs) at LISA and was very excited about this guy who had built a tool that worked the way sysadmins actually needed to work with a pragmatic, model-based approach. Even more importantly though, Luke was serious about fostering adoption, and had helped Jeff write some useful extensions for Puppet. Jeff had already gotten religion about idempotent, declarative approaches for sysadmins, and spent pretty much all of the bus ride bending my ear about this new project called "Puppet" and how it was going to change the world of operations.

After WWDC, I flew back to Australia, fully intending to try out this magical Puppet project, but got distracted by the day to day life of running campus IT operations on a shoestring budget for users who were academics and artists.

I was even more distracted a few months later when one of the MacEnterprise community members came out of lurking and told me I should apply for a role at Google in Mountain View. Several of the toughest interviews of my life followed, and within a couple of months, I was moving my young family to the other side of the world to run Mac Operations at Google HQ.

It was clear that tools like Radmind simply weren't going to work at Google for the many thousands of corporate Macs. Opinionated engineers who demanded a high degree of customization, immense growth, globally distributed offices and a very small team meant that it was completely insane to even think about trying the old methods of file-based config management of the entire system.

We needed a better and more sustainable way, a solution that gave us higher levels of abstraction with meaningful entities such as users, groups, services and packages, and that didn't require you manage the entire machine.

Jeff and I had kept in contact, and he was presenting on Puppet at WWDC that year. I popped up to San Francisco with some of my coworkers, and made sure we turned up to his talk.

10 minutes into his presentation we were getting pretty excited, and we started experimenting over VPN. By the time Jeff finished his talk, we had a working Puppet master back at Google managing the contents and permissions of a few critical files in /etc, and knew we had a great match.

As it turned out, the Mac deployment was such a rapid success that one of the Linux Ops team started a skunkworks project to manage the internal Linux distro with Puppet, as there had been a few failed CFEngine attempts. This worked so well that Puppet eventually managed all the Google corporate Mac and Linux desktops, laptops and servers.

Puppet was a much younger project in those days. We were building a lot of custom Puppet extensions for Mac OS X that went back into the core, and were having to scale Puppet to manage tens of thousands of nodes, so I spent a lot of time on the mailing lists and IRC channels brainstorming with Luke and the community. I quickly fell in love with the community. It was full of thoughtful sysadmins, people who were frustrated with the unreliable state of operations tools, and knew there was a better way out there than continually reinventing arcane bash/ssh frameworks.

We have some great technology with Puppet, but one of our greatest strengths is our outstanding community.

I ended up at the first ever Puppet Camp, San Francisco, 2009. It was small, but was one of the most exhilarating conferences I've ever been to. I love looking back at those photos and seeing how many of that group are now part of the Puppet Labs team. Dan Bode, James Turnbull, Ben Hughes, Gary Larizza, Michael Stahnke, Carl Caum, Deepak Giridharagopal (Little known fact: his last name is actually Tamil for "Grid Computing").

That's an awesome group of people to end up working with, let alone all the other great people we have here at Puppet Labs.

I had an amazing couple of years at Google, surrounded by super sharp minds and working on truly interesting operations problems at a scale greater than anything I'd ever touched before, but I was starting to look enviously at friends who left for early stage startups and the breadth of knowledge they were acquiring. Luke had poked me a couple of times about coming to work for him, but I didn't seriously consider it until late 2010 when he, Teyo and James made a much more concerted effort.

"You're opinionated about Puppet. Want to put your money where your mouth is?"

One visit to Portland and I knew I wanted to live in this awesome food, beer, and cycling-obsessed city full of people following obscure passions. I jumped ship from Google and we moved north, where I dived headfirst into being responsible for Product at a very quickly growing startup.

It's been an immense 18 months. We started with our first commercial release, Puppet Enterprise 1.0, and followed that up with several great releases, all solving real problems for real users. We've brought on the open source MCollective and Hiera projects from the incomparable RI Pienaar, released Puppet 2.7.0, and grown at an amazing pace. We’ve grown from 2 events a year to 15, including the incredibly successful PuppetConf `11 and are building up to an even bigger PuppetConf this year. Nothing like startup speed to quicken the blood.

From the original 20 odd folks I started with in the tiny office in the seedy and urine-drenched Old Town to our shiny digs in the Pearl, with over 80 employees. From a distinct lack of in-house beverages to decent espresso and delicious local beer. From a company that knew the user experience was critical, to one with a growing UX/Design department headed up by Randall of the impenetrable Gandalf gaze.

I love this company. I love what we’ve done already to change the face of operations, I love the ambition we have to change it even more, and I especially love the people I get to do it with.

I'm thrilled to take on the role of CTO, and to concentrate on fostering our culture of technical innovation so that we continue to build applications and platforms that truly advance the state of IT infrastructure. The world of operations is undergoing radical change right now. The cloud, pervasive virtualization, corporate adoption of FOSS, BYOD, IaaS, PaaS and SaaS are all forcing sysadmins to be truly agile and adaptive. Some of the brightest people in our industry work in operations, and it’s going to be incredible to see what they come up with when IT automation gives them space to concentrate on genuinely important matters.

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