What sales leadership and compensation models work for product-led growth firms selling to enterprises?

I think it depends on the stage a lot. Early-stage, especially when you have a product that is a self-serve bottom up product that is meant to expand over time, like the "land and expand" motion, it makes sense to hire go to market people early. But I don't think it necessarily makes sense to set a strict quota or comp them based on a quota because at that point, their goal might not actually be to get people to upgrade to an invoiced enterprise plan. The thing that might be best for the long-term value of both the company and that account might actually be to get them to self-serve upgrade at that moment, let them use the product over the next six months and slowly expand over time, and then come in and try to get them to upgrade.

Early on, I think quotas can be somewhat detrimental. In fact, what you're really trying to do early on is learning. When is the right moment for us to come in and turn this account into an enterprise account? What are the triggers that we can use to do this more scalably in the future? Early on, I think it's just a full normal comp package and salary, and the quota doesn't make as much sense.

Later on, it depends on what the model looks like. I think you see some companies that basically eschew most of the self-serve side of the funnel, and instead, they just say, "If it's a really small company or an individual, sure, they can self-serve. But if you are a real company greater than 100 employees, you're talking to a salesperson, and we're going to get you to upgrade to something. Then we're going to track that over time." In those scenarios, maybe it's so sales-led at that point that quotas are a requirement. But I think that there are other companies that rely much more heavily on the self-serve funnel and can probably get away with not doing quotas for a very long time because of that.