To infinity, and beyond

It’s hard to believe it’s been six and a half years. In late 2008 my startup had just collapsed, my wife and I were expecting our first child, we’d just bought a house… Oh yeah, and the world economy was shattering into fist-sized pieces of molten pain. Good thing I’d already burned through my savings – I didn’t have any money left to lose. People sometimes ask me why I joined TripAdvisor, and the honest answer is that they offered me a good job in a moment of need. It was only later that I realized how lucky I’d been.

TripAdvisor, it turned out, was recession-proof – 2009 was its best year ever, until 2010, then 2011, 2012, etc. It had an extremely strong engineering department, and was poised for tremendous growth. The people were incredibly nice. I’d never worked at a company so successful, and it turns out that when you strip away all the existential anxiety about making payroll, extracting a milestone payment from a reluctant client, or even just having a business model that makes any kind of sense, work becomes a lot more fun. Even when I joined, TripAdvisor was the biggest company I’d ever worked at, but it still had a sense of energy, excitement, and speed.

From the beginning, one of the best things about TripAdvisor was just how much you could learn, how much you had to. I was an experienced guy, I’d written a lot of code, managed teams, started a company, but this… This was moving up into the majors. SEO, SEM, scaling, architecture, testing and iteration – Trip was a true software engineering organization wrapped in a hacker mindset, and it was a phenomenal education in how the big kids played the game.

So I dug in, got heavily involved in recruiting, and went from managing one team, to two, to four, to six, at various times being responsible for Community, Social, Mobile, Sales, CRM, Listings, Tools, APAC, and Partner Integration. It was an amazing rollercoaster ride – there were successes and failures, good times and bad, but overall it was one of the most incredible periods of personal growth in my professional life.

Then, about a year ago, I made a change. Operations had always been a huge hole in my experience, and once again, TripAdvisor provided me with the opportunity to take a chance on something new. DevOps wasn’t initially my first choice, but it turned out to be the right one – a combination of tech-ops (hardware), site-ops (application layer), and warehouse (databases), it was the perfect learning opportunity.

I’m so grateful for everything TripAdvisor has given me, and it’s hard to say goodbye to my team, my friends, my mentors, and (if I’m being honest) the security of knowing how things work – but it’s time. Starting next week, I’ll be moving to a twelve person start-up in Cambridge. I’m already bracing for culture shock – all of the technology, infrastructure, processes, and systems we’ve built up over years will be gone. There won’t be dedicated teams to handle important, specialized tasks. Hiring was always important, but will suddenly be a matter of survival. And the tech will go from a traditional, fairly conservative Java-based n-tier stack to a JavaScript-heavy, responsive, single page app. It’s terrifying. It’s unbelievably exciting. And that’s how I know I’m doing the right thing.

So, to all my friends at TripAdvisor – and there are so many of you – you have my gratitude and admiration. It feels like we all grew up together, and built something great. Thank you, take care, and keep in touch.

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* The above image of an owl is © 2011 Tim Daniels. The image has been cropped to fit the space. It is licensed under a Creative Commons share-alike license.

8 thoughts on “To infinity, and beyond

  1. It was a pleasure to have (even briefly!) met you the other week; glad we had the opportunity to connect. Very best of luck in the new gig and I hope you keep blogging! Bon voyage!

    • Same here, Michael, and thanks! Let me know next time you’re in town, and we’ll go out for a beer or a bite or something.

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