Alex Payne is a writer based in Portland, Oregon.

since 2001, has served as his online home.

Moving On

Over two years ago, I flew across the country to spend hours in a basement in Brooklyn talking with two guys I barely knew. Those two guys were Josh and Shamir, respectively CEO and CFO of Simple (then BankSimple). When we first sat down, they had already put in months of work figuring out how to start a new kind of banking service. Josh and Shamir were ready to turn their vision of online retail banking with stellar technology, design, and customer service into a reality. I was ready for a new role and a big challenge.

During those first conversations, I asked Josh and Shamir where they saw themselves in ten years. Neither hesitated to reply “running this company”. Since then, I’ve witnessed their perserverance and dedication firsthand. Over the past two years the product has evolved from rough prototypes and a list of features on paper to a working, growing banking service. Today, Simple is bringing on customers by the thousands and rapidly becoming the center of their financial lives. It hasn’t been an easy thing to launch, but working on a product that addresses real problems at the intersection of economics and technology has been a fascinating opportunity.

While I’m extremely proud of the work everyone at Simple has done on the road to launch, I’ve come to recognize that the role of CTO isn’t right for me at this point in my career. Part of my motivation for joining Simple was to explore what it’s like to be a founder and executive at a startup. Being CTO afforded me the opportunity to work with and support a number of the most talented people I know. In that and many other respects it was a great experience. As with any job, though, there are tradeoffs.

The biggest tradeoff for me is that this role has taken me further from learning more about the craft of programming. Simple offers many great career opportunities for engineers, but not in some of the areas I’m most passionate about, particularly programming languages and developer tools. I feel that I have an enormous amount left to learn as a programmer, and hopefully a few things to contribute in that capacity as well. For that reason and some personal ones, I’ve stepped down as CTO at Simple.

My relationship with the team at Simple remains strong. The engineering organization there is in extremely capable hands. I have every confidence that the team will continue to do exceptional, industry-leading work. For my part, I’m staying on as an advisor to the company.

My next steps are to take some time off, relocate, and to consider my next move. This will be the first time in my adult life that I haven’t immediately gone from one job to another, and I’m looking forward to the perspective that a breather will lend.

I’d like to extend my thanks to Josh and Shamir for taking a chance on me, to the exceptional people who came to work with us, and to everyone who’s helped Simple along the way.

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