Confessions of a First-time Startup CTO

The struggles and glory of growing from a coder to leader

“I don’t think I can keep going.”

It came out of nowhere, so I just stayed silent.

“I mean I love coding. I love what we are building. I just don’t love my job.”

I first met Chris at an early mentorship session of the accelerator her startup attended. We were paired up based on similar industry experiences and found we had an instant rapport. Since meeting several months back, we got into a regular cadence of chatting every two weeks for advice and brainstorming.

Chris was the pragmatic, down to earth type. Never prone to exaggeration or overly expressive conversation, we tended to stick with more practical how-to topics and matter of fact things. Our chats were always technically minded, so this was new territory.

I replied, “What about the job do you not love?”

“Not sure, I just feel like I am failing at everything. There is all this other stuff I was never prepared for and the one thing I’m good at, coding, I hardly do anymore!”

Chris let out a sigh and looked away. This was the first time I saw her optimism turn to defeat as she seemed resigned to her inadequacy.

I have heard many similar thoughts from first-time CTO’s in startups. What I shared above is a real conversation, just with the name changed to protect the identity of someone that shared her personal struggles in confidence. The common thread in each conversation though is the feeling of not being suited for the role.

There are unique struggles and questions as a first-time startup Chief Technical Officer

The role of a Chief Technical Officer is not an easy one. There is the constant balancing act of keeping the engineering team productive and shipping reliable code with the need to be the technical ambassador to the executive team and board.

For CTO’s in early stage startups however, the stakes are higher. Often much of the initial codebase is the product of the CTO, who starts out as the first developer. Then there is the added pressure of building an entire engineering organization from the ground up. It is a huge responsibility that can humble the most confident of persons.