The CTO That Learned to Sell

Rising to the top requires more than technical skills

Mark

Feb 25, 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”.

Goodbye cake on United flight from Singapore — It was a lovely goodbye cake…

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.

I discovered there is a common term for this role called a Field CTO. They have been common to find in larger tech companies that sell technology to big enterprises. These customers tend to spend tens of millions up to billions of dollars with these providers, and Field CTO’s specialize in helping executives in these big companies understand the value of these investments.

The way you become a Field CTO is usually by being a former CTO or a near equivalent IT executive. I have seen Field CTO’s come from Chief Architect roles or Head of Cloud or SVP of Technology Operations. The point is that for someone to be credible in the role, they would have had to walk the walk and talk the talk by having the knowledge, experience, and credibility to understand and empathize with a customer’s CTO and other C-level executives.

AWS has a few teams that function like Field CTO’s, but under different names. One group is called Enterprise Strategy, a team staffed with ex-CIO’s of Fortune 500 companies and large government organizations. They work with CIO’s of our biggest customers to help them with questions about cloud adoption, transformation, cultural readiness, and other strategic topics. Often they take what they learn plus their own experiences and share those insights on the AWS Cloud Enterprise Strategy Blog, which is one of my favorite blogs to read.

Not every CTO is equipped to be a Field CTO. Some Field CTO’s quickly realize that the role is simply not for them. This is because the role requires more than just credibility. It is the rare individual that can have the depth of experience, the strategic outlook, the technical acumen, and the one thing that most technologists shy away from; selling.

The typical caricature of the techie is one of being shy, introverted, and avoids conflict or emotional engagement. This caricature has been the basis of most shows and movies about developers like Mr.Robot. The truth however is that the developers that have the most impact are sociable, have empathy, relish helping others, and can influence others. The most visible of these personas is the Developer Advocate. They are developers that are creating workshops and documentation, speaking at events, and building relationships with other developers.

Many will say that sales skills are not necessary in technical roles. Clearly developers and cloud engineers are not cold calling hundreds of leads or updating information in CRM. But there are activities that readily translate over to work a CTO does such as:

Fostering buy in for new initiatives
Forging partnerships to support initiatives
Managing and building stakeholder relationships
Presenting and pitching projects
Negotiating vendor contracts
Securing budget and funding
Tracking progress and metrics

If you are in a technical leadership role, you have a sales job.

There are times when the CTO has to do some of this sales work outside the company. On a previous AWS Startups Show, I interviewed a CTO that was very involved in the early days of their payments startup in sales calls. Because the customers were banks and the teams were very technical, they would have the CTO involved to lend credibility as well as to be a technical resource fielding questions during those customer meetings. Even CTO’s in enterprises can be customer facing when involved in forming strategic partnerships or being a key spokesperson for a new product launch.

It is hard to imagine anyone being successful as a CTO or technical leader without some basic level of sales acumen. Mostly it is just something that is learned and picked up along the way though. If you are not in a leadership role however but aspire to take on that role, there are few resources that can be helpful.

I like starting with books as they are a good first point in learning any new skill. I recommend the book To Sell is Human by Daniel Pink. I also share some thoughts in an earlier post on helping developers acquire sales skills. I wrote a series of posts on the AWS Startups blog about the ten key sales skills for technical startup founders, many of which are applicable for anyone in a technical leadership role or hoping to become one. Lastly, there are CTO community programs where we talk about many of these skills and more like CTO Connection run by Peter Bell, the CTO Fellowships the AWS Startups team runs throughout the year, and various regional groups.

How much do you value the sales skills in your own role and career aspirations? Of all the skills I mentioned above, which ones woudl you most like to improve?

Mark Birch, Editor & Founder of DEV.BIZ.OPS