On Leaving New York


After two years as a senior architect and senior principle in software development at Travelocity, Friday is my last day with the company. I joined Travelocity when the travel industry giant acquired the New York-based (and wonderful) startup Site59, where I had been the director of software development and hard at work building interesting and innovative applications and working with a number of really first-rate people.

I don't suppose I ever really intended to stay at as large (and as Dallas-based) a company as Travelocity for as long as I did. Particularly after they were reacquired by Sabre, an even larger company. But loyalty is a funny thing. One minute you don't think you feel it, and the next minute you're two years older and still wanting to see what see what the future holds. Moreover my colleagues, those that I had been closely working with for years, were more than co-workers -- they had become good friends.

And the scale of some of the technical challenges related to the travel industry captivated me. As did the directive to migrate a massive infrastructure off of legacy systems on to more contemporary systems, many of which I was able to design. On the up side, architecting systems that can handle the volume of such a massive site and designing algorithms for the myriad of travel-related problems is simply hard, and hard in a good way. On the down side, tackling problems of that magnitude often require a cast of hundreds, and there are greatly diminishing rewards when team sizes grow to be that big.

However, I wanted to get back to my startup roots (such as Tripod, Eziba, and the defunct Avacet), where the immediacy of every-day problem solving is paramount and it never takes a back seat to bureaucratic wrangling. There is a level of excitement when working with a small team at a small company that simply can not be matched by an organization with thousands of individuals. I missed the little things, such as knowing everyone's name in the company, and quietly set about looking for a new position.

I put out a few feelers to see if the venture capital market was loosening up enough to start something myself. But, as I learned well enough in the past, those things take time and an ungodly amount of patience and luck, so I wasn't holding my breath. I actually did get a lot of positive feedback and interest about a new caching architecture I have been working on, but short of someone walking up and handing me a couple of million dollars, I wasn't about to quit my literal day job.

Then I saw something about a new search company that had inauspiciously just gone beta this spring. Amazon's new subsidiary, named A9, seemed to be in the perfect spot. A9 had a mandate to innovate in search technology and had the financial (and operational) backing of one of the most successful of all "internet revolution" companies. And from what I could see on their beta site, they had the vision and skills to deliver. (I particularly liked the search histories, and saw such a huge potential for the multi-source data aggregation.) So I dusted off my résumé and sent it over to them.

A few days later I was speaking on the phone with their CEO (whom I actually knew all about by reputation and some famous open source software he had built). A few days after that I was in Palo Alto being treated to a rather thorough seven straight hours of interviews. Halfway through the day I had already decided that I would take the job if offered it. By early the next week I had accepted.

The entire process was the most professional, and enjoyable, interview/offer experience I had been through (perhaps second only to getting the program manager job with Microsoft, but I was too young to really appreciate that one at the time). In fact, I wanted to work for A9 not simply because of the opportunity to invent exciting new technologies and work with brilliant people, but also because everything I saw of them was straightforward, honest, and above board. (Prospective employers would do well to take note of that. Far too many companies come off as indecisive, poorly organized, or worse, unethical, in the interview process, and undoubtedly lose quality applicants as a result.)

Perfect job aside, it was partly bittersweet news, as A9 is based in Palo Alto, CA. While the bay area is fantastic, and I have a fondness for San Francisco, my family, my friends, and my life are all around NYC. I briefly entertained a daydream of jetting back and forth between coasts on the weekends, keeping an apartment in each city. Then I realized that was nuts. I would simply have to say goodbye (or rather, farewell), to NYC for a little while. (I'll be back to open up the NYC office of A9 just as soon as I come up with a clever enough justification for it.)

Two parting thoughts on this. One, if A9 sounds good to you, send us your résumé. We are looking for the best and brightest. And two, there will be a going away party. One big enough and rowdy enough that my leaving town for a little while might just be a really good idea...