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Daniel Doubrovkine

aka dB., CTO at artsy.net, fun at playplay.io, NYC

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My job title has recently changed from Head of Engineering to CTO, and many people outside of Artsy have been asking me to explain the logic behind this. A more important question is what is the difference between a CTO and a VP or Head of Engineering? Are these different jobs? Is it all about the title and why do titles matter at all?

A company has many possible successful outcomes. Organizations iterate and find a business by trial and error. The job of a CTO is to continuously ensure that all possible outcomes are enabled with technology, while the job of a VP or Head of Engineering is to execute on the outcome currently chosen.

What do I mean by all possible outcomes? A brilliant example of business transformation enabled with technology is Amazon, which began by selling books, but succeeded at becoming an infrastructure company and an e-commerce behemoth. Amazon continues to innovate and experiment heavily and explore many new business opportunities, but is also executing very well.

These two jobs are different responsibilities, but involve a lot of doing the same kinds of things. A CTO carries a unique responsibility of placing technology within the non-engineering organizations and to represent the technology point-of-view with investors or the board. They help everyone take a step back and look at the big picture with tech in mind, while a VP or Head of Engineering helps individual contributors and leads focus on the tasks at hand and drums up the beat of continuous delivery. When done right this yields a healthy tension that strikes the balance between short, medium and long-term thinking.

An Internal or an External Facing Job

Sometimes this difference is referred to as an external vs. internal facing job, which is also true but doesn’t tell the whole story. A big part of remaining competitive with technology is understanding the business, competition and the entire technical landscape, which means looking out vs. focusing on product delivery, which is looking in. Practically being a CTO means being less focused on the day-to-day in order to avoid getting caught up in your own bubble and missing the next big turn, sinking a company into years of painful un-digging from their own systems. Microsoft is a prime example of a very profitable corporation that completely missed the open-source bandwagon and is now trying to catch up at a massive cost, vs. Facebook. Similarly, media companies are generally failing at digital streaming, unlike MLB, which has invested in streaming tech ten years ago and is now riding its huge competitive advantage.

Do Titles Matter?

Titles don’t matter much in a small organization, and you definitely want to avoid title inflation in early stage startups. That means using less shiny titles, such as Lead vs. Director or Head of Engineering vs. VP of Engineering. This emphasizes company mission over beefing up individual resumes. That said, you won’t be at your current job forever, and giving people titles that represent their job clearly to other people outside of your company is important, particularly relevant for jobs that require a lot of external relationships.

Thanks

What I do every day has not changed. But I now try to focus a bit less on product delivery and more on longer term or outward facing tech. This is only possible because I have incredible Engineering leads working with me, and they have taken on all of the software systems. I am always thankful and feel privileged to have so much freedom to organize my time whichever way I want!

I also want to thank Camille who should be credited the majority of my CTO vs. VP or Head of Engineering definition above and Carter for working so hard on the Artsy company culture and contributing most of the thinking around titles.