Hiring is always challenging, though hiring in a startup is a unique beast. I believe that every hire must immediately be placed into two buckets.
They are either a builder or a strategizer.
Builders are people who identify a problem and fix it. They are often considered to be engineers, but in reality they can be anywhere from the sales team to product management.
Strategizers mostly anticipate future problems and put together processes to mitigate those issues. These are people who may traditionally be thought of as senior management, but they can be any level.
The goal is a startup is the hire the appropriate ratio of builders to strategizers.
Too many builders and the company can build too far in the wrong direction. Too many strategizers and the company won’t move forward fast enough.
The ideal startup hire is getting someone to who is both willing to build and able to strategize. They should start as a builder until they learn enough and can hire builders to replace them. And they must have the social awareness to manage those who they hire.
This build / strategize ratio is essential to any company. But in a startup leaning too far one way or another can lead to the death of a company. After all, one wrong hire in an organization of around 20 means that your company is structured 5-10% incorrectly.