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Assuming that I don't know anything about or have zero experience in the skill-sets I am hiring for, how does one start? What questions to ask, what to look for and where to look for the talent?
So for instance try doing marketing yourself for a month. One benefit: you may discover you're good at it and don't need to hire someone, or hire someone freelance or part-time. The more important benefit: when you're interviewing a candidate, you know what you're looking for and can explain what you need from experience.
You are over complicating. Start with one person and grow from there. The 1st person is the most important
Can't speak from experience, but my recommendation would be to never hire someone to do work you've not done yourself. (I believe Joel Spolsky mentions this.) So for instance try doing marketing yourself for a month. One benefit: you may discover you're good at it and don't need to hire someone, or hire someone freelance or part-time. The more important benefit: when you're interviewing a candidate, you know what you…
What stage is your business? Pre-rev, rev, profitable? What business are you in? What part of the world are you located? Are you looking too go remote, hybrid or Co located?
Really you need an advisor if I take these questions at face value.
If you have funds to be able to hire a team (esp cyber security), then you've likely raised money or made money. If you've raised money your investors should be able to deeply help you. If you've made money, I feel like you would know what you need more than anyone here and you should just interview for your biggest problem you can't solve yourself.
If you really need the second person to do something critical that you cannot do yourself consider a cofounder, not an employee. My 2c.
The best thing is to know a lot of people and just happen to know somebody who can help you. The second best is to scour the internet and your network for people who are good at what they are doing. Trying to hire your first person on a job board is probably the worst thing you can do.
Rather than start with a position, start with the person and figure out how they can help you given their skills and personality.
This is not the time to standardise your positions, you have to make best use of the flexibility that startup setting provides and use that flexibility for your advantage.
You will have to give them a lot of freedom anyway.
Don't hire people who can't deal with ambiguity and/or need a good precise description of what they are supposed to do. Most of the work is defining what you are supposed to do so you will be getting very little value out of them if you have to provide all of the direction.
If you are starting with a vision and try to force somebody into that vision then you are already fighting an uphill battle.
Can't speak from experience, but my recommendation would be to never hire someone to do work you've not done yourself. (I believe Joel Spolsky mentions this.) So for instance try doing marketing yourself for a month. One benefit: you may discover you're good at it and don't need to hire someone, or hire someone freelance or part-time. The more important benefit: when you're interviewing a candidate, you know what you…
Do you have a good guide on how to "try doing marketing yourself for a month"? To me this shit is so alien, I can't imagine I'll even scratch the surface in a month.
How will you be able to discern a charlatan from a good fit to your company, if what they're supposed to be at at is totally alien to you?!
Go to the library, ask around, google. Even if you completely fail at marketing, you've learned something about the skills you're missing. Which your company is missing.
You start by doing the tasks you need done yourself. When you learn what is needed and can't manage it yourself anymore then you know what to ask and hire for.