Given the current market I'd say you have to achieve some basic success before hiring anyone, at least if you're bootstrapping. From my experience it's quite difficult to find early-stage employees that are both affordable and good enough to handle the breadth of technical tasks needed in the early phase of a business.

So, yeah, automation can take away a lot of pain, and how far you can get really depends on how well you automate specific aspects of your business. My takeaway after several SaaS products is that you have to optimize for minimal customer interaction from the start, otherwise you'll drown in support requests once you hit product-market fit. Stuff like billing, subscription management etc. should be solvable in self-service processes for customers, and if you see a speficic support issue more than 5 times in a given week you should ask yourself if you can automate it away or change the product so it won't happen again.