Hiring for roles outside of their area of expertise is one of the biggest challenges start-up founders face.
The early phase of a software start-up is usually characterised by rapid product experimentation, selling to “friends and family” and a lack of formal structure or processes. During this phase, hiring enthusiastic generalists typically works very well for founders.
Once the business starts scaling however, the pace of everything increases, including the volume and complexity of paying customers.
It is at this stage that organisational gaps, a lack of specific skills and process shortcomings can start to negatively impact paying customers, with things like slow deployments, product quality issues or low user adoption generating negative customer sentiment and even a loss of existing revenue.
A founder’s natural instinct when faced with these kinds of issues is to fill the organisational gaps by creating a Customer Success function and to bring in the domain expertise they lack by hiring the most tenured Customer executive they can find.
This instinct to hire in a tenured executive makes total sense, but it is not always the right one (and can be costly to the business and its culture).