The purpose of this document is to provide some clarity around our hiring philosophy, which covers concepts like who we hire, when we hire, and other ideas related to hiring.
This document supersedes ‣, which is hereby deprecated. All ideas from that document that are still relevant have been incorporated into this document.
Some companies prefer to hire from a place of pain, while others prefer to hire proactively when there are roles they know they have upcoming. There are no right answers here, as both have costs and benefits.
One of the biggest advantages of hiring proactively (meaning, hiring someone in advance of experiencing pain from the lack of a person in that role) is that you can grow more comfortably and it's lower stress on the team. It also allows you to appropriately invest in your hiring pipeline and process so that you don't feel pressured to make a hire quickly, which can lead to a better hire at the end of the process.
Hiring proactively reduces the chances that you end up making a hire out of desperation. I've been in this situation personally where I was so underwater that I was willing to hire anyone who had even the faintest chance of getting me out from under my workload. I should have made more of a priority to hire someone months earlier, but by the time I needed to make it a priority, I was so underwater that I didn't have the time to put together a job description or go through the hiring process.
The most obvious downside of proactive hiring is that it increases burn, but in general, if you're hiring this person a few months earlier than you otherwise would, the amount of cash you'll spend on them to bring them on earlier is ultimately negligible.
Probably the most likely risk of proactive hiring is that, at an early stage startup, you don't really know what you'll need until it becomes painful. In large corporations, there are well defined positions that you need to fill on a regular basis with clearly defined job descriptions and responsibilities. In a startup, the roles you're hiring for might be completely different in 6 months — in fact, the entire company strategy might be different in 6 months!
At our stage, there are only a few circumstances when we should consider hiring proactively:
As a general rule, at the current stage of our company (~25 people), we should default to hiring from a place of pain rather than hiring proactively. It's only when we have a clear understanding of gaps in areas of responsibility that we should bring someone on full-time to solve for that problem.