The CTO That Learned to Sell

Rising to the top requires more than technical skills

DEV.BIZ.OPS

6 min readMar 4, 2022

I am heading back to Singapore for the first time in nearly two years. In fact, when I leave later today, it would have been exactly 23 months when I got on a plane from Singapore back to the US thinking I would be back soon.

We all thought we would be going back. Even though the plane was full of United flight crew returning to the US on what was the last United flight between Singapore and the US, we figured it was just a short pause. There was even a cake brought on board from the Changi Airport ground crew and said “Come back soon”.

When I first started traveling to Singapore for business, my main objective was to build up Stack Overflow’s business in Asia. While we sold access to our job board and offered an ads product, my main focus was to spread the word about our Teams product for internal knowledge sharing and collaboration. This meant talking to heads of engineering and CTO’s.

What do you do when you know absolutely nobody in a part of the world you are unfamiliar with? My first stop is LinkedIn because that is where the professionals and executives tend to have online profiles. LinkedIn can be a funny thing though because titles are not always the best indicator of what a person actually does.

The title of CTO, Chief Technology Officer, seems self-explanatory. In nearly every case I have ever come across, a CTO is a leader of technology teams that sets the technical vision. The scope may differ, for example startups usually have just one CTO whereas an enterprise will have many, but they do many of the same things to build the team and execute the vision.

When I would reach out to some portion of CTO’s though, they were not technical leaders of teams. They did not even have a single team reporting to them. They owned no goals nor did they track metrics on product deliverability or the business value of technology. They had no authority or decision making power on any technology initiatives or programs. They were CTO’s in name only.